AI to ROI (fka Metrics that Measure Up)

Pricing is one of the most underleveraged strategic levers in B2B SaaS and AI Software. Most companies are getting it wrong. In this episode, Ray Rike sits down with Dan Balcauski, founder of Product Tranquility and a 20-year software industry veteran, to cut through the noise around consumption, usage, outcome, and hybrid pricing models. Dan brings a practitioner's perspective on when to review pricing, who should own it, and how the CFO fits into the equation.Signs Your Pricing Needs a ReviewBest-in-class companies review pricing at least quarterly -- but review does not always mean changeKey warning signals include declining net revenue retention and unexpected shifts in win/loss conversion ratesAI-native companies are iterating on pricing monthly due to rapid competitive dynamicsSales cycle length is a practical constraint: a 12-month enterprise cycle limits how frequently you can test and observe pricing changesThe Role of Customers in Pricing StrategyNever anchor your pricing strategy entirely to your existing customer base -- they carry inherent biasA practical research mix: roughly one-third existing customers, two-thirds prospectsExisting customers know your real value; prospects only know what you show them -- both perspectives matterWhen introducing a second product, maintain structural similarity in pricing tiers even if the pricing metric differsPricing Ownership and GovernanceBelow $5M ARR, the founder/CEO owns pricing; above $20M it shifts to Product or Marketing -- the gap in between is where ownership gets dangerously vagueProduct Marketing is best positioned to own pricing because it sits at the intersection of positioning and value communicationSales owning pricing is a misalignment of incentives -- "like putting Dracula in charge of the blood bank"Best practice is a pricing council with a designated decision-maker, not design by committeeDiscounting and the CFO's RoleDiscounting policy is often the easiest and fastest win -- and one of the first places Dan looks with any clientEnforcement matters as much as policy: without monitoring, no new pricing strategy will ever reach the market as intendedThe CFO plays a dual role -- operational (contracts, billing, deal desk guardrails) and strategic (modeling cash flow and KPI impact when shifting pricing models)Caution: A finance-led focus on consistent margin profiles across products can misread how different market segments actually behaveOutcome-Based Pricing: Hype vs. RealityOutcome-based pricing is "the future and always will be" -- it is not new, and it is genuinely difficult to executeTrue outcome pricing only works when you are directly in the revenue or savings transaction, as Stripe isA more practical frame is output-based pricing -- Intercom's 99 cents per resolved support ticket is a strong example of measuring a clear, attributable unit of valueIf you are involved in how best to monetize and price your B2B AI or SaaS product - this is a very valuable listen!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

While the AI headlines obsess over foundation model fundraises and hyperscaler spending, a quieter revolution is generating real, measurable returns. In this episode of AI to ROI: The Big Story, Ray Rike and Peter Buchanan break down why vertical AI companies may be building the most durable and valuable businesses in the history of enterprise software, and why most people aren't paying attention yet.What's covered in this episode:Defining Vertical AI: What separates vertical AI from horizontal tools like Microsoft Copilot or Google Workspace AI, and why the distinction matters for buyers and investors alikeA fundamentally different business model: Why vertical AI companies target labor budgets (10x the size of enterprise software budgets) rather than IT spend, and how outcome- and consumption-based pricing is replacing the traditional per-seat modelThe funding explosion: Vertical AI investment grew from $8B in 2023 to $22B in 2024 to $42B in 2025, with unicorn counts in the sector jumping nearly 6x in just two yearsHarvey (Legal AI): How this $8B+ valuation company grew ARR from $100M to $190M in just four months by orchestrating multiple AI models across legal workflows and embedding deeply into law firm operationsAbridge (Healthcare AI): How a cardiologist-founded company reached a $5.3B valuation by turning physician-patient conversations into structured clinical documentation in real time, with deep Epic EHR integration across 150+ health systemsSierra (Customer Experience AI): How Brett Taylor's enterprise AI platform hit $100M ARR in just 21 months and crossed the $10B decacorn threshold, raising the question of whether the agent era could produce the first trillion-dollar enterprise software companiesMaintainX (Industrial/Manufacturing AI):How this maintenance management platform is tackling $1.4 trillion in annual equipment failure costs across 11,000 customers and 11 million assets — with a 34% reduction in unplanned downtime for customersWhy vertical AI moats are so durable: Proprietary data that compounds with every transaction, embedded institutional knowledge that makes switching costs higher than any legacy ERP migration, and a model architecture that gets stronger as foundational models improveAdvice for enterprise buyers: Why 2026 is the year to evaluate vertical AI vendors, insist on outcome-based pricing, and start with one workflow before expandingInterested in reading the details on the Vertical AI industry and trends? Check out the AI to ROI Newsletter providing even more detail by clicking here.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of the AI to ROI Podcast, host Ray Rike sits down with Amanda Kahlow, founder and CEO of 1Mind. Prior to 1Mind, Amanda was the founder and former CEO of 6sense, an early pioneer in intent data.The Vision Behind 1Mind: Amanda founded 6sense to help companies find buyers; she founded 1Mind to close them. 1Mind builds what she calls "go-to-market superhumans", AI agents that take on multiple roles across the full customer lifecycle, from inbound qualification and live demo delivery to deal closing for SMB/commercial accounts, and even post-sale onboarding, upsell, and cross-sell motions.Why the Buyer Journey Has Fundamentally Changed: Amanda argues that traditional intent data and one-way marketing are becoming obsolete. Buyers no longer follow a linear path of Google searches and form fills; they expect real-time, two-way, solution-oriented conversations, much like they get from interacting with large language models today. The old model of blasting outbound emails or routing inbound leads through a sequential SDR → AE → SE handoff chain is increasingly misaligned with how modern buyers want to engage.Top Use Cases: How Customers Deploy 1Mind: The most common starting point is the inbound website use case, customers start by placing a superhuman on the website that can qualify a visitor, deliver a personalized live demo, answer deep technical questions, and in some cases take the deal all the way to close, all on first touch. From there, customers frequently expand to the "ride-along" use case, where the superhuman joins every sales call as an always-available AI sales engineer. Human sellers retain control but can call on the superhuman in real time to answer hard questions, surface the right case study or slide, run an integration demo, or ask the qualifying questions (MEDDIC and similar) that sellers often avoid.Measurable Business Impact: Amanda shares compelling early results from enterprise customers, including a ~40% reduction in sales cycle length (from ~90 days to ~60 days) and a doubling of ACV for deals that passed through the superhuman pipeline versus the traditional pipeline. She attributes the ACV lift to getting buyers to vendor-of-choice status earlier in the cycle, eliminating the need to compete on price. 1Mind also has use cases for existing customer bases — proactively engaging customers about new features to drive upsell and cross-sell, a task that human CS teams increasingly can't keep pace with, given the speed of product development.How Customers Measure ROI: Amanda is direct: the right measurement framework is revenue impact, not top-of-funnel pipeline metrics. She encourages customers to tie superhuman performance to shortened deal cycles, higher ACV, and bottom-of-funnel revenue influence. She acknowledges there is a maturity curve — some customers start by measuring meetings booked — but the companies seeing the most value are those willing to shift away from MQL-based thinking toward board-level outcomes: revenue growth, lower CAC, and expansion revenue.Onboarding & Time to Value: 1Mind has invested heavily in its self-serve platform to reduce deployment time from a four-month process to an average of about four weeks today, with some customers going live in as little as four days. All deployments are full enterprise contracts, as 1Mind does not run pilots.Advice for Leaders on AI ROI Amanda emphasizes that realizing meaningful AI ROI requires a top-down mandate from the CEO. Incremental point solutions can improve efficiency at the margins, but the big needle-movers require new playbooks and organizational willingness to change how work gets done, not just layer AI on top of existing processes.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

On this AI to ROI Big Story episode, our hosts Ray Rike and Peter Buchanan dig into Deloitte's 2026 State of AI Report, a 41-page annual study surveying over 3,300 business leaders on the state of enterprise AI adoption. Deloitte calls it "The Untapped Edge," and Ray and Peter unpack exactly why.They walk through the report's seven key inflection points from scaling pilots into production and reimagining business processes, to agentic AI, sovereign AI, and physical AI, with a focus on what the data actually means for companies trying to drive real ROI in 2026.Key topics covered in this episode include:Pilot to Production: Why 54% of respondents expect a major leap in production deployment in the next 3–6 months, and why 37% of companies are still making little or no change to existing processesProductivity & Revenue: How 66% of organizations report efficiency gains today, but only 20% are seeing actual revenue impact from AI - and what it will take to close that gapBusiness Transformation: Why 84% of companies have yet to redesign jobs around AI, and what that means for long-term competitivenessAgentic AI: What the jump from 26% to 74% expected adoption of agentic AI over two years signals, and the top enterprise use cases including customer support, supply chain, R&D, and cybersecurityGovernance: Why only 21% of companies have a mature governance model for autonomous agents, and what leading companies are doing to build responsible frameworks from the ground upSovereign AI: How 83% of multinational board members view sovereign AI as at least moderately important, and why the US, Europe, and the Middle East are approaching it very differentlyRay and Peter close with a clear-eyed summary of what enterprises need to do now: close the gap between strategy and operational readiness, redesign work with an AI-first mindset, and shift focus from incremental efficiency to genuine strategic reinvention.📰 This episode is based on the February 19th edition of the AI to ROI newsletter. Subscribe at ai2roi.substack.comSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Is the trillion-dollar AI bet actually going to pay off? In this episode of AI to ROI, hosts Ray Rike and Peter Buchanan tackle the big question head-on: with hyperscalers pouring over $600 billion into AI infrastructure this year alone, enterprises struggling to move pilots into production, and white-collar job postings already falling 16% year-over-year, the anxiety is real and justified. But so is the optimism.Ray and Peter break down why the same supply constraints slowing AI buildout may actually give companies and workers more time to adapt, why foundation model costs have plummeted 97% since 2023, and how IBM's internally deployed AI has already generated $4.5 billion in productivity savings. From healthcare transcription to AI-native go-to-market tools, the ROI is emerging, but not evenly or quickly enough for most.What We Cover in This Episode:The staggering scale of AI infrastructure spending: The five largest hyperscalers (Amazon, Microsoft, Alphabet, Meta, and Oracle) are on track to spend over $600 billion in CapEx this year, with Oracle committing 57% of its annual revenue and Microsoft 45%, ratios more typical of heavy industrial companies than software firmsWhy the build-out is slower than everyone thinks: Grid upgrade timelines in the US run 8+ years, data center construction is broadly behind schedule, and critical shortages in chips, transformers, skilled labor, and construction materials aren't expected to ease until at least 2028The pilot-to-production gap is real: Only 6% of enterprise AI projects are delivering returns within a year, and most organizations lack the frameworks and experience to move from experimentation to operational deployment at scaleTrust, hallucinations, and governance are still major blockers: Regulated industries like financial services and healthcare face compounding uncertainty, caught between pre-AI regulations still on the books and a patchwork of conflicting state, federal, and international AI policyThe workforce impact is already being felt : Salesforce cut 4,000 customer support roles, Klarna reduced headcount by 40%, white-collar job postings are down 16% year-over-year, and college graduate placement rates have dropped from 83-88% to roughly 23%, hitting data science, software development, and graphic design hardestBut the technology itself is accelerating fast: Foundation model costs have dropped 97% since early 2023, the number of available models has grown from 60 to 650, and enterprises are getting smarter about orchestrating multiple models for different tasksReal ROI stories are emerging: IBM has generated $4.5 billion in productivity savings from internally deployed AI since January 2023, automating nearly 4 million hours of work annually at $3.50 returned for every dollar investedVertical AI is gaining serious traction: Healthcare AI is the fastest-growing vertical, with one transcription tool alone saving 50,000 clinician hours. Legal, cybersecurity, customer support, and IT operations are all seeing meaningful gainsThe competitive pressure is intensifying: 54% of business leaders in a Mercer study believe they won't remain competitive in five years without AI at scale, and 92% of firms plan to increase AI budgets over the next three yearsWhy You Should Listen:If you're a business leader, investor, or professional trying to cut through AI hype and understand what's actually happening on the ground, this episode delivers the balanced, data-driven perspective that's hard to find. Ray and Peter don't just cheerlead or catastrophize; they give you the real picture: where the bottlenecks are, where the returns are genuinely showing up, and why the next two to three years of slower-than-expected adoption might actually be the window your organization needs to get AI right.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What does it actually mean for an ERP to be AI-native and why does it matter for your finance team? In this episode of the AI to ROI podcast, host Ray Rike sits down with Santiago Nestares (Santi), Founder and CEO of DualEntry, to unpack the real differences between legacy ERP systems and a ground-up AI-native platform.Santi shares the origin story behind DualEntry, born from a painful nine-month ERP implementation at his previous company that cost a team of 12 and hundreds of thousands of dollars—and explains why simply adding AI features on top of old database architecture misses the point entirely. AI, he argues, isn't a feature you plug in; it's a design philosophy that must be embedded at every layer of the product.Ray and Santi dig into one of the thorniest challenges in enterprise finance: the tension between probabilistic AI models and the zero-error standard that accounting demands. Their answer? Deterministic guardrails—approval workflows, permissioning layers, and audit trails—that let AI work freely in draft mode while keeping humans accountable for every posted transaction.You'll also hear about DualEntry's "Next Day Migration" approach, including how the company uses AI to map and migrate every transaction (not just trial balances) in hours rather than months, giving prospects a live sandbox with their own data before they ever sign a contract.What You'll LearnWhy adding AI to a legacy ERP is like "running an on-prem system with a CD on the cloud", and what truly AI-native architecture looks like insteadThe difference between deterministic and probabilistic systems, and why accounting can't afford to get it right only 99.9% of the time without the right guardrailsHow DualEntry's Next Day Migration works: AI-assisted mapping, atomic transactions, and a live sandbox demo using the prospect's own dataThe real ROI of AI-native ERP from eliminating manual categorization drudgery to enabling multi-dimensional segmentation that surfaces hidden pockets of value and riskHow Dto build audit-ready explainability without being able to explain the AI itself - by tracing every decision back to a human approvalWhy early-career finance professionals are "living the luckiest time" in the professionand how to lean into AI rather than fear itEpisode Topics at a Glance00:00 — Welcome & guest introduction00:51 — Santi's origin story: a nine-month legacy ERP nightmare that sparked DualEntry02:52 — AI-native vs. legacy ERP: what's the real difference?04:48 — Deterministic vs. probabilistic systems explained06:49 — How to identify a truly AI-first platform vs. an AI add-on10:07 — Next Day Migration: using AI to accelerate ERP transitions14:11 — Implementation team design: finance practitioners + forward-deployed engineers17:18 — Measurable ROI: from real-time bank feeds to AI-driven business insights22:52 — AI explainability, audit trails, and the permissioning layer25:06 — Rapid fire: CFO ROI variables, who owns AI ROI, and advice for early-career finance professionalsSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Is your company leaving money on the table by not having a Chief AI Officer? In this episode, Ray Rike and Peter Buchanan dig into groundbreaking research from IBM's Institute of Business Value, spanning 600+ executives across 22 geographies and 21 industries to unpack why dedicated AI leadership is quickly becoming non-negotiable for enterprises competing in today's market.The numbers tell a compelling story: only 26% of companies currently have a CAIO, yet those that do are seeing 10% higher ROI on their AI investments and are 24% more likely to outperform their peers. And that gap? It's widening. With 66% of existing CAIOs predicting most organizations will have someone in this role within 24 months, the window to gain a first-mover advantage is open — but not for long.Ray and Peter go deep on some of the episode's most surprising findings, including:Who's actually getting hired: 73% of CAIOs come from data-focused backgrounds, but the most effective ones are hybrid leaders equally fluent in business strategy and data science. And 57% were promoted from within, because institutional knowledge often matters more than technical expertise.Where they sit in the org chart matters enormously: CAIOs who report directly to the CEO and control the AI budget (61% do) drive far greater results than those positioned as glorified advisors without real authority.The hub-and-spoke model delivers 36% higher ROI: companies that pair a centralized AI function with embedded business unit partners outperform those with fully decentralized AI decision-making, giving them both governance and agility.Three pillars that make or break a CAIO: measurement tied to real business outcomes, cross-functional teamwork across the entire C-suite, and genuine authority to make tough decisions. Strip away any one of these and ROI suffers.What to do if you're not ready to hire one yet : Ray and Peter offer practical alternatives, from AI steering committees to centers of excellence, and explain why accountability can't be an afterthought regardless of your company's size or structure.They also tackle the growing complexity of managing AI at scale, the average large enterprise is now running 11 generative AI models and why the rise of agentic AI makes centralized leadership even more critical before things become, as Ray puts it, "a hot mess."Whether you're a Fortune 500 executive or a mid-market leader trying to figure out your AI strategy, this episode is packed with data-backed insights to help you move from AI experimentation to measurable, scalable ROI.Prefer to read more detail - check out the AI to ROI Newsletter covering this topic at: ai2roi.substack.com/p/the-chief-ai-officer-from-nice-to?r=2ldi4pSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This episode of the AI to ROI podcast, hosted by Ray Rike and Peter Buchanan, explores how leading SaaS companies are surviving the "SaaSpocalypse" - a massive market cap devaluation triggered by the rise of AI. The hosts break down the transition from traditional SaaS to AI-first models, emphasizing that simple "feature bloating" isn't enough; companies must undergo a fundamental "organ replacement" of their architecture, pricing, and culture.The discussion deep-dives into three success stories:Notion: Transformed from a document suite into an agentic execution platform through strategic acquisitions, moving toward autonomous workflows.Canva: Democratized design by making AI features invisible and intuitive, resulting in a 700% increase in AI tool usage and massive revenue growth.ServiceNow: Leveraged its 20-year history in workflow automation to pivot from seat-based pricing to task-based pricing, using AI agents to orchestrate complex enterprise processes.If you are a SaaS company executive looking for great examples of how they transitioned to be AI-first - this episode is full of great examples, strategies, and tactics.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode, our host Ray Rike sits down with Jacco van der Kooij, founde and CEO, Winning by Design, to discuss the real-world deployment of "Jack" - an AI SDR that has spent the last 12 months redefining the front line of Go-To-Market (GTM) strategy. Jacco shares the "AHA" moments and hard truths discovered while moving beyond human constraints like slow response times and inconsistent qualification. Discover how treating an AI SDR (agent) as a "system" rather than a "product" initially led to 2,030 conversations, 100% CRM capture, and a $200,000 deal.Episode SummaryWinning by Design set out to prove that if AI can handle the high-risk, high-empathy role of an SDR, it can work anywhere in GTM. Over the course of a year, their AI agent, Jack was built on a foundation of 1mind logic and Clay enrichment. The agent evolved from a simple chatbot into a trained GTM operator.Key Highlights:Breaking Human Constraints: The project addressed critical issues like burnout, limited global coverage, and poor CRM hygiene that even the best human reps struggle to maintain.The "AHA" Moments: Jacco details how the team realized Jack shouldn't just "chat" but perform industrial-scale qualification while supporting buyers in their buying journey.The Power of Iteration: Initial surprises, such as a low 8% email capture rate, were overcome by designing a better "value exchange" rather than just tweaking prompts.Tangible Results: After refinement, email capture jumped to 20%, MQL conversion rose by 36%, and the system successfully captured nearly 9,000 SPICED answers.The Ultimate Do’s and Don’ts: Success requires anchoring the agent in a GTM system and iterating weekly; failures stem from treating AI like an unstructured chatbot or deploying without clear ownership.The Do'sDesign the value exchange first: Ensure the AI provides something useful to the buyer before asking for informationEarn the next step: Focus on providing enough value to merit the next stage of the conversationAnchor the agent in your GTM system: AI should scale a pre-designed, structured system rather than an improvised process.Start narrow, then expand: Focus on one specific motion and one outcome before attempting to scale.Iterate weekly: Small, frequent changes to the system drive the most significant gains in performance.Focus on the buyer's journey: Design the experience to help the buyer buy, rather than just helping the seller sell.The Don'tsTreat AI like a chatbot: Avoid unstructured "chatting," as it kills conversion rates; focus on industrial-scale qualification instead.Chase volume over quality: Remember that activity is not the same as a healthy pipeline.Hide the AI behind humans: Be transparent about using an AI agent to build trust with the buyer.Deploy without ownership: AI implementation is a Go-to-Market responsibility, not just an IT project.Expect AI to fix a bad process: AI will not fix poor GTM design; it will only expose and amplify existing flaws.Point AI at unstructured data: Do not simply point the AI at a massive folder of research; start with specific, high-quality training materials.If you are considering deploying agentic AI into your Sales organization and process, this episode is full of great insights, experiences, and measurements for your AI investment in Sales.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Are we witnessing a productivity revolution or the greatest labor displacement in history?In this detailed episode of AI to ROI, Peter Buchanan and Ray Rike break down the "Great AI Jobs War," a period of massive upheaval where corporate gleefulness meets workforce anxiety. They move past the "AI washing" to find the real metrics that define success in the age of intelligence.Key Discussion Points:The Historical Context: Ray draws parallels between the AI revolution and past disruptions like the Industrial Revolution, the cotton gin, and the assembly line, noting that AI is moving with a magnitude and speed never seen beforeThe "Mother May I" Productivity Gap: While 47% of S&P 500 companies now discuss AI in earnings calls, only 10% are seeing meaningful ROI, leaving a "staggering" 56% of companies getting "little to nothing" out of their implementationsThe Million-Dollar Employee: A deep dive into Klarna’s radical transformation—reducing headcount from 5,000 to 3,000 through attrition while doubling revenue to reach the "magic number" of $1.1 million in revenue per employeeThe War on Early Careers: Why entry-level IT hires have plummeted from 25% to 7% of all hires, and the "structural problem" of junior roles requiring 2–3 years of experience because AI is now doing the "digital grunt work"Blue-Collar as the "Gold-Collar" Future: Why the CEO of NVIDIA suggests young people skip computer programming for mechanical trades, and how salaries for AI-related construction and electrical roles have doubledCustomer Service Autonomy: How Bank of America's "Erica" handled 2 billion interactions with a 98% resolution rate in under 44 seconds, signaling a massive shift in how businesses handle scaleActionable Insights for Leaders:Measure Revenue Per Employee: This is the ultimate metric for AI productivity.Bake AI Aptitude into Hiring: Every new white-collar job description should require "AI curiosity" and applicable tool skills.Strategic Augmentation: The goal isn't just headcount reduction, but using the "free cash flow" from AI efficiencies to build a war chest for growth and sales.To read more details and subscribe to the AI to ROI Newsletter for more data-driven strategies on turning AI hype into bottom-line results.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In the second episode of AI to ROI: The Big Story, Ray Rike and Peter Buchanan analyze the critical transformation required for traditional SaaS companies to become AI-first organizations. With the SaaS industry generating $273 billion annually, the hosts warn that incumbents are under "two-front" attack: internal refactoring of legacy systems and external disruption from hyper-efficient AI-native startups.Key Highlights of the Episode:The "SaaS to AI" Pivot: Ray compares the current shift to the on-premise-to-SaaS transition of 20 years ago, noting that today’s change requires a fundamental rewrite of an operating culture rather than just adding "AI veils" like prompt enginesThe Rise of AI-Native Efficiency: Peter highlights companies like Lovable and Cursor, which have achieved hundreds of millions (or billions) in valuation in under a year with minimal staff, challenging the traditional SaaS model of linear employee growthThe Shift in Financial Metrics: The hosts discuss the new economic reality: forgetting 80% gross margins in favor of a 50-65% range to account for high token and inference costs. Success will depend on the "COGS to CAC" model, offsetting higher infrastructure costs with dramatically lower customer acquisition costs via AI automationA Roadmap for Success: To fight back, SaaS incumbents must re-architect around outcomes rather than features. This includes leveraging their "crown jewel data" and status as systems of record to build decision intelligence layers that AI-native startups lackThe HubSpot Success Story: Ray details how HubSpot successfully scrapped its 2023 roadmap within weeks of ChatGPT’s launch, shipping AI-native products in under 90 days and moving toward a "Results-as-a-Service" futureAdvice for Leaders and Employees: Ray suggests that CEOs must re-engineer every department to be AI-first, while employees should commit to learning new AI tools every month to remain employable in an increasingly automated landscape.Listen to the full episode for a deep dive into how to avoid becoming an "orphan" SaaS company in the age of Agentic AI.You can read the newsletter edition covering this topic by clicking here.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of the AI to ROI podcast, host Ray sits down with Drew Laxton, CFO at Outreach, to explore the profound transformation of sales technology and financial metrics in the age of AI. Drew shares the strategic reasoning behind his return to Outreach, driven by a conviction that the company is uniquely positioned to lead the next era of agentic AI and automated revenue workflows.The conversation goes beyond the hype, offering a masterclass in how finance leaders must adapt to a software landscape that is moving from seat-based subscriptions to consumption-driven models. Drew provides an inside look at how Outreach is re-engineering its own financial playbook to account for the high compute costs and non-linear revenue growth associated with AI.Key discussion points include:The "Personal Productivity" vs. "Financial ROI" Debate: Why the initial wave of AI efficiency must eventually translate into higher quotas and lower OpEx to satisfy the board.Maintaining Margins in an AI-Native World: A deep dive into the "triumvirate" of Product, Engineering, and Finance that manages gross margins as compute costs replace traditional SaaS overhead.The Metric Recalibration: Why traditional SaaS snowballs don't work for AI, and how Outreach is using "spend-as-truth" to normalize data for NRR and CAC calculations.Agentic AI in Action: How Outreach's "revenue agents" are replacing manual prospecting with autonomous, data-tuned interactions that learn from previous customer engagement.Some Key Insights and Quotes pulled from the conversation with Drew:On the "Boring" Wins of AI: While many look for revolutionary shifts, Drew emphasizes the value in automating the mundane:"A lot of the AI tools that I’ve seen so far... there's kind of boring outcomes that are very impactful... like our QA process within the coding side has very much streamlined."On the Changing Economics of SaaS: Drew acknowledges that AI-native products fundamentally alter the 80%+ gross margin expectations of the past decade:"We do need to bring gross margin into our understanding of SaaS tools because it's just not the same... You've got to be more efficient on the go-to-market side to make the economics work."On the Rise of Consumption Pricing: The shift to variable pricing means the "snowball" metric of the past is no longer sufficient:"What is your ARR has become a lot more challenging question than it used to be... consumption is not linear on these products. It’s kind of zero, very little, and then a lot."On the Importance of Usage Over Revenue: In a variable world, product utilization becomes the primary indicator of a healthy business:"Product utilization... becomes a core signal to retention. It's not just revenue anymore, it's utilization month by month... spend is truth."Advice for Aspiring CFOs: For those looking to reach the C-suite in the AI era, Drew suggests one primary trait:"Be curious. Just be curious about everything... Ask questions, get time with the CFO or the leaders of the various organizations... wanting to understand their business has only benefited me."See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In the first episode of the AI to ROI: Big Story podcast, our co-hosts Peter Buchanan and Ray Rike discuss the emerging importance of Context Graphs in AI Software.Why are context graphs suddenly being called a trillion-dollar opportunity in enterprise AI? In this inaugural episode of The Big Story, hosts Ray Rike (CEO of Benchmarkit) and Peter Buchanan (Managing Partner of New Plan) dive into the "glue technology" that fills the missing gap in the AI stack.While traditional knowledge graphs tell you what happened, context graphs reveal the why! Context Graphs capture the decision traces, policy constraints, and precedents that make AI agents truly auditable and trustworthy. From preventing "data breakage" in regulated workflows to revolutionizing supply chain quality control, discover why context is the key to moving AI from experimental pilots to reliable production.Key TakeawaysThe Why Behind the Action: Context graphs provide the connectivity that agentic AI lacks, recording who made a decision and under what specific constraints.A Trillion-Dollar Value Add: Industry leaders believe context is a massive economic value driver for companies in the era of AI.Beyond Knowledge Graphs: Moving from simple data points to decision lineages that explain the "why" behind an event.Real-World Use Cases: Deep dives into data governance at firms like Vanguard and Prudential, and quality control in the automotive supply chain.The Vendor Landscape: Discussion on current players like Atlan, Neo4j, and Writer, and why tech giants like Microsoft and Salesforce are the "lurkers" to watch.Timestamps00:00 Introduction to the AI to ROI podcast series.02:40 Defining Context Graphs: The missing gap in the AI stack.04:15 The Trillion-Dollar Opportunity: Economic value vs. market size.06:30 Knowledge Graphs vs. Context Graphs: Moving from "what" to "why".09:20 Who should care? Roles from the CEO to the Chief Risk Officer.12:45 Use Case 1: Data Governance and preventing "downstream breakage".15:10 Use Case 2: Unifying the Go-To-Market (GTM) stack.18:30 Use Case 3: Supply chain visibility and automotive quality control.21:40 The Market Map: Current leaders and "Lurker" strategies from Big Tech.25:50 Executive Summary: Things every leader must do right now.Context graphs are a key component to turn Agentic AI software vision into Agentic AI explainability!Read the AI to ROI Newsletter on Substack to dive deeper into this week's Big Story!Subscribe at: ai2roi.substack.comSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Welcome to the first episode of AI to ROI, the newly re-imagined evolution of the highly successful Metrics That Measure Up podcast. In this launch episode, our host, Ray Rike sets the stage for a new era of conversations focused on turning artificial intelligence from hype into measurable business outcomes.The inaugural guest is Todd Olson, Founder and CEO of Pendo, who joins the show for an interactive, unscripted discussion on how companies should measure the real impact of AI agents inside modern SaaS and cloud organizations. Together, they explore how AI-driven “digital workers” are reshaping productivity, workflows, and operating models across the enterpriseKey topics include how companies can measure the performance and business impact of AI agents, the emerging metrics that define agent adoption and activation, and why connecting usage data to tangible outcomes like time saved, cost reduction, and revenue impact is critical for ROI. Todd also shares his perspective on outcome-based pricing, why it remains rare in AI-native software today, and what must change for it to scale.The conversation wraps with a forward-looking discussion on SaaS and AI convergence, as agents increasingly appear on org charts and product roadmaps, followed by practical advice on developing AI competencies for the next generation of business leaders.If you care about moving beyond AI experimentation toward measurable economic value, AI to ROI is your new go-to podcast.Subscribe, rate, and follow AI to ROI on your favorite podcast platform.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

The world of FP&A is having its day in the spotlight. New pricing models, a new focus on near real-time business planning, the increased focus on balancing revenue growth and profitability, coupled with the dynamic impact that AI is having on the SaaS market, are all making the role of FP&A a more strategic asset. Albert Gozzi, is the founder and CEO of Aleph, a modern FP&A platform and company that recently raised $29M in their Series B financing from Khosla Ventures.During today's episode, our host, Ray Rike is joined by Albert Gozzi, Founder and CEO Aleph, to discuss the strategic future of FP&A including:The vision behind founding AlephThe evolution of AI in FP&AFP&A’s role in developing corporate strategyGrowth strategies being used in a crowded categoryIf you are a finance leader, FP&A professional or fellow B2B SaaS founder with a product purpose built for the Office of Finance, this conversation with Albert Gozzi is full of unique insights, ideas and opportunity to make your Financial Planning and Analysis organization a strategic asset!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Think about the unparalleled growth that OpenAI has experienced since the public introduction of ChatGPT on November 30, 2022. Now, think about being in finance, or being the controller who had to scale their financial processes, including closing the books to keep up with a company that has scaled from less than $100M in revenue to $10B+ in less than 3 years!?!?That was the situation that Sowmya Ranganathan, Former Controller OpenAI and CEO, Lumera found herself facing in the early part of 2023.During today's conversation with Sowmya, our host Ray Rike discusses several important lessons and use cases of AI at OpenAI in the Finance department including:Why there was no existing playbook for scaling Finance in a company like OpenAIChallenges in one of the fastest growing software companies of all timeUnderstanding compute expenses is critical to understanding the financial performance today and tomorrow at an AI companyWhy excel could not work at the scale of OpenAI (1M+ rows)Using OpenAI to enable finance to write the python code to write the statistical model to analyze financial dataWhy historic analysis is not a good place to start for forecasting in a hypergrowth, compute intensive companyLeveraging AI in the Financial close process - leveraging data warehouse information to build a repeatable processTracking GPU costs in real-time throughout the month - not an excel scale requirementHallucinations are a real concern - but once your AI is encapsulated as standard code - the concerns are minimizedHuman review on any stochastic model is a best practice - such as contract data fields from signed contracts to establish billingA long description would not do the conversation justice - so jump in and be ready to pause the audio to capture the highlights.Sowmya has been in financial leaderships at Square and Rippling in addition to OpenAI, so she has a very unique perspective on not scaling finance to meet the unparalleled growth at OpenAI, and two other hyper growth companies. If you are interested in learning about real-life stories of using AI in Finance at the world's largest AI software company - this episode is a must listen!!!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Christina Ross is the founder and CEO of Cube. Prior to founding a SaaS platform purpose built for everyone of those companies still using Excel (majority of companies) for business modeling but want to enhance the collaboration of business budgeting, planning and performance across the company, Christina was a corporate audit executive at GE, financial transformation consultant at Deloitte and a multi-time CFO at companies including Rent the Runway, Criteo and Eyeview.During today's episode, Christina and our host, Ray Rike discuss multiple aspects of the Financial Planning and Analysis role, department and the strategic opportunity for FP&A to materially increase the impact on business strategy and performance. Topics we discussed include:How the experiences at larger companies including GE and Deloitte shaped her view on the strategic role of FP&AThe biggest challenges facing CFOs with the FP&A function todayThe role of FP&A in business strategyThe impact of FP&A on business performanceIf you are a CFO, FP&A leader or even the CEO this episode is full of great insights and ideas on how to increase the business impact of your FP&A function!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Exit Ready Analytics is a concept that any B2B SaaS company CFO and CEO should become familiar with before entering into any potential strategic company sell initiative, deal due diligence and/or data room preparation.During this episode, Will Sullivan, Managing Partner at Predictive Analytics Partners discusses his experiences from over $30 Billion in strategic acquisitions across 20 transactions. Topics discussed include:Exit Ready Analytics - the when, what, and howThe differences between a strategic Chief Revenue Officer and a Head of SalesWhen to hire a CRO and their responsibilitiesHow to bridge the CRO and CFO relationshipIf you are a CEO, CFO or CRO in a B2B SaaS company that is either considering a strategic sell process and/or want to increase the strength of the CFO and CFO relationship - this episode has something for you!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Imagine leading Finance for a company that has made 31 acquisitions over the last six years. Then, imagine the challenges of having near real-time visibility into a recently acquired company to ensure the forecast accuracy that a Private Equity firm expects from their portfolio companies, specifically from their CFO.That is exactly the environment that Josh Schauer, CFO at insightsoftware, operates in every day! During today's episode, we discuss three main topics that are part and parcel to achieving near real-time insight into the data, performance metrics, and trends required to drive financial decisions - quickly. Those topics include:The challenges with fragmented data for financial decision-makingMoving from historic to real-time data for Financial decision-makingDeveloping a process to quickly integrate acquired companies into your financial systemsModifying budgets based on actual performance insightsIf you are considering private equity as a potential exit strategy, or are part of a company that is growing through acquisition, this is a must-listen-to episode!!!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Casey Woo, Founder and CEO of the Operators Guild has a very interesting journey, from being a West Point cadet, a Harvard graduate, an investment banker at Goldman Sachs, a multiple-time CFO and now the founder and CEO of the Operators Guild, and General Partner at Fog Ventures. With this background Casey has been able to experience and identify the critical role of the "scaler" in companies.During the conversation with Casey we cover multiple topics including:The role of the scaler versus specialist in businessThe personality traits of a scalerHow process and performance interact from a scaler's perspectiveHow the Operators Guild became a community of scalersIf you have ever felt that one department, one role and doing the same thing day over day was not fully leveraging your skill set and talents - this conversation is thought provoking and inspirational.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Melissa Howatson is the CFO of Vena Solutions, a $100M+ ARR cloud-based financial planning and analysis (FP&A) platform that helps companies streamline budgeting, forecasting, reporting, and financial modeling, with a strong emphasis on Excel integration.During the episode, we covered multiple topics with Melissa including:Latest trends in B2B SaaS FP&AAI in Finance - the importance of change managementMetrics that Matter at > $100M ARRMeasuring the Impact of a podcastThe 30-minute conversation hit upon multiple key trending topics including: 1) how FP&A is evolving as a strategic business partner to the other key functions; 2) why the CFO needs to lead a culture of experimentation with AI; 3) how EBITDA increases in importance as a company scales and; 4) how to measure the impact of a company sponsored podcast!If you are an aspiring CFO, or a CFO looking to scale your company beyond $100M ARR or are interested in how a world-class CFO came to be this conversation has something for you!!!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Marcos Rivera is the founder and CEO, Pricing I/O. Marcos has a long career as a B2B Software operating executive and now leverages that experience to help B2B SaaS and AI-Native companies optimize monetization, pricing, and packaging.9 ingredients for a winning pricing strategy9 psychology concepts for pricingDifferences between SaaS and AI pricingThe value of pricing frameworksMarco was the head of pricing and packaging at Vista Equity, one of the top Private Equity firms in the B2B SaaS industry - an incredible foundation to see how leading companies leverage pricing as a strategic growth lever.Marcos started by sharing the key ingredients to developing a winning strategy, explains all nine, and highlighted why he believes the top four are most critical:Knowing the compelling value that our software deliversEstablish a clear market positionPricing that builds trustCase studies and ROI proof Have a pricing point of viewConsistent pricing messagingData-Driven pricing insightsSocial proof and testimonialsOngoing price optimizationAnother key topic discussed was the 9 psychological concepts for pricing, including:Halo effectLoss aversion (FOMO)Social proofConfirmation biasScarcity effectMere exposure effectAnchoring effectAuthority biasGoal gradient effectIf you are responsible for creating, testing, refining, or selling B2B SaaS or AI-Native products - this episode is a great way to understand the "why and how" of pricing - not just the what!!!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Shane Murphy-Reuter, GTM President at Calendly, has been part of multiple B2B SaaS companies during their hypergrowth phase, including Webflow, ZoomInfo, and Intercom. He recently joined Calendly to integrate the Go-to-Market functions and continue to find new opportunities to increase growth and growth efficiency. Shane is responsible for creating a more seamless customer experience across each stage of the Calendly customer journey. During today's episode, the discussion covers a wide variety of topics including:The Primary Role of the GTM Executive in a PLG CompanyThe key inflection points in scaling a PLG companyHow to evolve a brand - from the buyer’s perspective How to build an integrated GTM team in a PLG companyOne of the key aspects of this conversation is that we dive deep into how to leverage and apply B2C best practices in a B2B and PLG environment - at scale. Another key insight here is the importance of becoming a multi-product company and evolving the brand of a primarily self-service, single-product company.If you are evaluating or recently transitioned to an integrated GTM organizational structure that begins and ends with the customer experience in a Product-Led Growth environment - this conversation is for you!!!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Josh Aharonoff, better known as "Your CFO Guy" and the founder of Might Digits, a consultancy specializing in accounting, finance and fractional CFO services. Josh has amassed 450,000+ followers on LinkedIn, which is extremely rare for anyone, especially someone who caters to the corporate finance community!During Josh's appearance on the Metrics that Measure Up Podcast, he and our host, Ray Rike discuss a wide variety of topics including:The Role of the Fractional CFOWhen to consider an internal VP Finance or CFOWhy excel is a CFOs best friend…or NOTBuilding a LinkedIn following of 450K+ - the business case and the processIf you are a small or medium size business CEO, and are interested in when it might be the right time to bring in a VP Finance or CFO, or a finance professional looking to scale-up your personal brand, want to enhance your excel skills or considering starting your own business this conversation with Josh is chalked full of great insights, ideas and best practices!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Dan Miller, CFO at RightRev, has been at the center of Usage-Based Pricing, having served as CFO at Fastly and previously as VP of Finance and General Manager at NetSuite. During today's episode, Dan and Ray discuss how Usage-Based Pricing and AI Outcome-Based Pricing are impacting ARR Reporting and Revenue Recognition Management.During today's episode, Dan and Ray cover several emerging trends in SaaS and Native-AI companies including:How variable pricing models impact revenue recognitionHow does the evolution of Outcome-Based pricing impact revenue recognitionHow AI is and will impact the Office of FinanceA few key takeaways from the episode that are worthy of a deeper dive and listen include:Understanding how contract modifications impact revenue recognition policy, process, and reportingBlended offerings including a fixed fee + usage are great for customers - but hard to manage revenue recognitionHow token and credit-based pricing impacts revenue recognition and gross profit calculation and reportingThe strategic impact and tactical challenges of transitioning from pure subscription or hybrid Usage-Based PricingIf you are a CFO or SaaS executive looking to better understand how pricing trends are challenging existing revenue recognition processes, infrastructure, and automation - this episode is a great listen!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

There is a famous saying that goes something like this "Half of my advertising (marketing) investment is wasted, the trouble is I do not know which half". This quote is credited to John Wanamaker over 100 years ago, and many marketers feel the same in 2025!Pranav Piyush is the founder and CEO, Paramark and they are attempting to make this quote not quite as relevant or correct in the future. Paramark is a marketing measurement and optimization platform designed to help businesses understand the true impact of their marketing efforts across various channels. By leveraging advanced statistical methods and machine learning, marketing and finance teams are better enabled to make data-driven decisions with confidence.During today's conversation with Pranav, we cover a wide array of topics including:Aligning Marketing Investment to Outcomes - that matter to a CFOThe concept of incrementalityHow to anticipate and measure channel specific diminishing returnsBrand vs Performance measurementsThe top 3 metrics a CMO should be sharing with their CFOIf you are B2B Marketing leader responsible for budget and delivering an ROI on that budget, or a CFO looking to better understand how to measure the ROI on marketing expenses, this episode is a great listen.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

B2B Marketing and AI Trends are evolving rapidly in 2025, and who better to discuss those trends with than Sydney Sloan, Chief Marketing Officer at G2 - the leader in B2B Software reviews!During today's episode we discuss a wide array of topics with Sydney including:Marketing Budget Allocation for B2B tech companies in 2025Peer reviews and their impact on B2B SaaS purchasesThe growth in AI - as measured by categories and vendors with G2 reviewsThe opportunity to exploit the power of AI for B2B MarketersIf you are in the B2B SaaS industry, a B2B SaaS Marketing executive or a B2B SaaS customer this episode has something for you!!!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

The Data and Sales Intelligence category includes a list of well known players such as ZoomInfo, Seamless and Apollo, and are now joined by new entrants like Clay and Lusha. But where does a pure play Data (Sales) Intelligence provider like People Data Labs fit - their CEO, Brian Eisenberg who has grown through the ranks at People Data Labs from Data Engineer to CEO provides his insights in how the Sales (People) Intelligence category is evolving.During today's episode, our host Ray Rike discusses multiple topics with Ben including:The top challenges customers are facing with today’s Data Intelligence solutions?How does People Data Labs ensure they remain compliant with the evolving data privacy laws and vendor specific Terms of ServiceHow will next generation Data Intelligence solutions address the current challengesBen’s personal career journey - from Data Engineer to CEO in 7 yearsIf your B2B SaaS or technology company uses Sales Intelligence Data to feed your outbound machine - this conversation is a must listen!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Bill Koefoed is the CFO of OneStream which went public in 2024 after being acquired by KKR in 2021. The CFO journey from being a Private Equity owned company to preparing for an IPO and beyond, while also transitioning from a perpetual license model to a subscription business is a fascinating experience and story.During this episode, Bill and Ray discuss a wide variety of topics and experiences during this CFO journey including:How the role of CFO changes in a Private Equity majority owned B2B SaaS companyThe lessons learned in transitioning from a perpetual license to a B2B SaaS subscription modelThe preparation required to take a B2B SaaS company publicHow technology has changed the Office of Finance and the CFO roleThe journey to becoming a B2B SaaS CFO - the Bill Koefoed pathBill mentioned that he had previously been the CFO of a Private equity-owned company. Once you have the first experience under your belt, your reputation as a Private equity-experienced CFO will be the access ticket to the next CFO position.Bill highlighted the importance that pricing plays when first starting the transition from perpetual to subscription. The cross-over or break-even point was targeted at 5 years, which essentially says that beginning in Year 6 the benefit of operating in a subscription business model materially increase.Bill shared the metrics that he prioritizes, and he started with the 98% Gross Revenue Retention Rate which highlights their priority and focus on customer satisfaction. In addition, Net New ARR, Net Revenue Retention and how much of Net New ARR is coming from "new customers" versus customer expansion. In fact, new logo acquisition is a top focus for 2025, including going from 1,600 customer to 10,000 plus new customers.  New customer ARR contributes about 60% of the total new ARR.What customer acquisition efficiency metric does Bill use - he really likes LTV:CAC Ratio and the CAC Payback Period which they currently stand at 24 months - but that is with a $340K ACV!If you are a CFO in a B2B SaaS company, or are an executive leader looking to evolve into a private equity acquisition or initial public offering - this conversation with Bill Koefoed, Chief Financial Officer at OneStream is an enlightening conversation that covers a broad variety of insights, experiences and inspiration!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Aviv Canaani is the Chief Revenue Officer at Datarails who recently transformed their Go-to-Market motion to be primarily inbound from the traditional outbound motion. During today's episode Aviv and our host, Ray Rike dive deep into multiple GTM strategies and measurements including:Top performance measurements for a B2B SaaS CROThe catalyst for transitioning to an "inbound GTM motion"The ROI for an Inbound vs Outbound GTM motionLeveraging Social Media to build awareness with the Office of FinanceMeasuring ROI in content and media investmentsAviv was initially the head of Marketing and then took overall responsibility for Sales, Marketing, and Customer Success. Soon thereafter, he quickly realized that they needed to increase the efficiency of their Go-to-Market investments and associated processes. But before we dive into the transition from a 90% outbound strategy, we discussed the top metrics for CROs.First, Aviv highlighted that CAC efficiency, as measured by the CAC Payback Period (CPP) where they have decreased the CAC Payback Period by 50% is a TOP metric for CROs. One of the first topics we discussed was the primary "input signals" to decrease the payback period. One of the things Aviv highlighted is that increasing the quality of leads that are provided to AEs was a good first place to start. The ultimate goal was that AEs could spend the majority of their time on selling and closing opportunities, versus doing cold outbound prospecting.Another key tactic was to ensure he had a very predictable way to know for each dollar investment in Go-to-Market, what the expected outcomes as measured by new customer ARR could be generated. Using a "waterfall" methodology, Aviv knows that for every dollar of Marketing spend what are the predictable outcomes as measured by meetings, opportunities, new customers, and the associated new ARR.By having a predictable model, Aviv can go to the CFO and confidently show what the ROI is for every dollar invested in Marketing, they can begin to allocate more to brand building which will have more impact in a few quarters versus just measuring the short-term ROI on Demand investments.Next, we dove into the transition from a primarily outbound GTM motion to primarily an inbound GTM motion. First, in 2022, even though SDRs were hitting their "meeting goals" they were not converting to customers. As a result, they increased the focus on "high intent" leads which increased the efficiency of the GTM investments. One of the primary measurements they used to validate the inbound focus, they found a 3x-4x higher win rate, and a shorter sales cycle all leading to increased GTM efficiency.What is the primary source for 90% of new ARR coming from inbound? First, they brought on a team of B2C Marketing professionals who used paid search, paid media, and social media strategies to drive higher intent inbounds. This even included the use of Instagram and TikTok...to reach the Office of Finance! In addition, they focused on SEO and even a podcast to get their brand and message in front of finance executives. Now that the brand has been enhanced through the media investments will over time also increase the efficiency of the outbound activities.Another strategy was to divide outbound and inbound SDRs, and in fact, a majority of the outbound SDRs are now located in the Philippines which maintained effectiveness and increased efficiency as measured by outputs (New ARR) versus inputs (SDR investments).If you are a B2B SaaS CFO or GTM leader, this conversation with Aviv is full of ideas, insights, and successful experiences in evolving the GTM playbook!!!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This episode of the “Metrics that Measure Up” Podcast features James D. Wilton, Author of Capturing Value - The Definitive Guide to Transforming SaaS Pricing and Unshackling Growth and Managing Partner, MonevateDuring our conversation we covered four primary topics with James:Actual Value versus Perceived Value - which matters mostPrice Metric Evaluation CriteriaInnovative Monetization StrategiesMeasuring a Customer’s Willingness to PayIf you are considering changing your existing pricing model and/or introducing new pricing for either an existing or new product - like a new AI module, this conversation is loaded with great ideas and insights into the different pricing models being used in the B2B SaaS industry!!!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

SaaS Pricing is evolving to better align the value received to the pricing model. The trend to using new pricing models including Usage-Base Pricing, Value-Based Pricing and Outcome-Based Pricing is evolving quickly and Bill provides his insights into the current trends and future of SaaS and AI pricing.During the episode Bill and Ray discuss several trends including:The top trends in SaaS pricingHow SaaS companies are adapting their pricing modelsThe risks and rewards of changing pricing modelsOverview of the FAST "Pricing Page" FrameworkBill’s crystal ball on where AI pricing is headedIf you are evaluating evolving your SaaS pricing model - this is a highly informative and instructive conversation.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Enterprise Resource Planning (ERP) has been the foundation for larger companies dating back to the introduction of SAP R-3 in the late nineties. Sandeep Chopra, Co-Founder and Co-CEO of Everest Systems says that ERP vendors have lost their "customer focus" and believes their is a large opportunity to re-invent ERP in the cloud to help companies run their business more efficiently. Introducing Next Generation ERP to the SaaS industry is the first step.During today's episode our host Ray Rike and Sandeep discuss the next era of ERP includingThe need for a next generation ERP platformAdvantage of leading edge technology to re-engineer business processesWhat stage of company should evaluate ERPOffice of Finance use cases for leveraging AIBenefits of integrating accounting, billing and planning in one platformIf you are currently a Quick Books user and/or are evaluating the benefits of an integrated accounting, billing, revenue management and planning platform this conversation is full of interesting ideas and business reasons to consider this strategy.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

The Rule of X is a recently published SaaS metric that factors in the relevant importance of growth rate and operating profitability for B2B SaaS companies. Sam Bondy is the co-author of this metric and shares the catalyst for creating the metric, the latest trends and how the Rule of X impacts Enterprise Value to Revenue multiples.Sam joined me as a speaker at the recent SaaS Metrics Palooza to provide the details behind the metric and why it is an important metric that helps to evolve the traditional Rule of 40 metric.This episode is part of the "SaaS Metrics Palooza" re-load series on the Metric that Measure Up podcast.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

SaaS buyers complete ~70% of the buying process before they speak to a vendor's sales organization. As a result more and more SaaS companies are leveraging interactive product demonstrations on their website which is the topic of today's episode. Natalie Marcotullio, Head of Growth at Navattic discusses their recent "State of Interactive Product Demonstrations" with our host Ray Rike where they cover multiple topics including:The State of Interactive Product DemonstrationsTo Gate or Not to Gate - what is the best practiceMeasuring the Impact of “Self-Directed” Interactive DemonstrationsIn 2024, almost 12% of SaaS companies are providing interactive product demonstrations on their website which is an increase from 9.3% in 2023. Surprisingly, 73% of interactive demonstrations are not gated, and one primary reason is that non-gated interactive demonstrations have a 10% higher engagement rate.How do we measure engagement on interactive demonstrations? Natalie highlighted four: 1) Number of users who get past step one of the demo; 2) Number of users who complete the demo; 3) Users who click at least one CTA to an external resource and; 4) time spent on the interactive demonstration.Of course, at the end of the day measuring the outcomes from an investment in an interactive demo is critical, and the top two metrics that Natalie recommends include the number of qualified leads and win rate from those leads and users who engaged with the interactive demonstration.If you are looking for new ways to engage with your target buyers and ensure your product is initially understood and evaluated by potential buyers, this is a great conversation to understand how to introduce and leverage the power of self-guided, interactive demonstrations on your website!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

The possibilities of combining AI with the collective intelligence from hundreds of B2B companies to increase their customer acquisition efficiency are limitless. Stephen Messer, Founder and CEO of Collective[I] shares his unique insights into how the potential is becoming a reality for many B2B companies. During today's episode, Stephen and our host, Ray Rike will cover the following topics:The vision behind founding Collective[I] and the Economic Foundation ModelWhy buyer’s historic behavior is more important than a selling processThe challenges and benefits of a “give to get” collective for go-to-market data sharingIf you have ever used Waze to identify the shortest time from where you are to where you need to go, you understand the value of "collective intelligence". When you start to think about being able to understand which companies are most likely to buy your product and/or to understand why a specific customer buys, and who are the key decision makers you need to engage with, the possibilities that come to mind are limitless!Stephen shares how a Neural Network (AI) is being applied to Go-to-Market data to help B2B companies materially increase the ROI on their customer acquisition investments.Stephen shares how his experience founding LinkShare and the concept of affiliate networks is foundational to Collective[I]. Over 10 years ago, Stephen identified that salespeople create a new "roadmap" for every new opportunity. He envisioned building a network where everyone shares their sales process data anonymously so that the collective group can benefit from the collective wisdom generated by the group.The result was building one large neural network and creating an economic foundation model trained on how buyers buy from real-world processes.One of the fundamental premises is that companies cannot build their own neural network and thus not build their own foundational model - as they do not have the insights required into how new target companies actually buy.If you are responsible for leading a B2B Sales team, rely upon a sales team to achieve your financial plan, or are an individual sales professional who would like to know more about how a target customer or existing prospect buys, this conversation is one of the most thought-provoking discussions that we have had on the Metrics that Measure Up podcast.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

SaaS company acquisition velocity will increase in 2025 and the role of marketplaces purpose built for buyer and sellers will become a must visit for both. If you are considering selling or buying a SaaS company, this discussion with Andrew Gazdecki, Founder and CEO at Acquire.com is a must listen. During the episode Andrew and our host, Ray Rike cover the following topics:The catalyst for founding Acquire.comThe trends in B2B SaaS start-up and early stage company acquisitionsTop lessons learned from the insights of hundreds of B2B SaaS acquisitionsSome of the key insights shared during the episode include:The value of preparing for the Confidential Information Memorandum (CIM)The importance of a discovery call with buyers prior to the Letter of Intent (LOI) The role of international buyers for U.S. companiesValuation expectations need to be realistic and reflect the current realityEBITDA is key for companies under $5M - know the current rangesDeal structures are widely varied - be open to different structuresGrowth Rate, Churn and Quality of Revenue are key metrics to highlightIf you are considering selling your SaaS company or a buyer thinking about buying an existing SaaS company, this conversation with Andrew Gazdecki, Founder and CEO of Acqiure.com is a must listen!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

HubSpot was an early mover in building a media asset inside a B2B SaaS company with the purchase of The Hustle in 2021. Rob Litterst is the Head of Growth for the HubSpot Media Network which has expanded far beyond those early days in building out their media network!During today's episode, Rob and Ray discuss many aspects of building, growing and measuring the business impact of a media asset within a B2B SaaS company including:The vision for building a media asset within a B2B SaaS Company Measuring the business impact of an internal media assetLessons learned from growing the HubSpot media networkIf you are a Chief Marketing Officer considering how or if to build a media brand within your B2B SaaS company, or a CFO or CEO considering approving the investment in developing media assets in our SaaS company, this conversation with some who have been involved in doing it at both ProfitWell (acquired by Paddle) and HubSpot provides insights that only come with the experiences of doing it in two of the industry's best examples!!!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

AI Monetization Strategies - Balancing Revenue and Adoption with Gary Survis and Ethan DeSilva, Insight Partners was a top rated session at SaaS Metrics Palooza '24 that is a can't miss conversation for anyone in SaaS interested in how B2B SaaS companies are introducing, pricing and monetizing AI functionality.Key points covered during this conversation include:Is it the time to charge existing customers moreAI Scalability Gap from individual tasks to cross-functional workflows is a challengeAdoption before MonetizationAs value increase the monetization strategy will evolveIf you are considering launching new AI functionality in your SaaS product or already have and are rethinking the pricing strategy this episode is a great listenSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Poya Osgouei has been responsible for securing sponsorships for some of the largest B2B events including SaaStr, Lenny's and Friends Summit, Elevate by Plato and shares his insights on the future of B2B tech events.During this episode, Poya and Ray discuss the following topics:The state of B2B tech eventsThe future of B2B tech eventsCommunity, Brand or Revenue - the "why" behind B2B tech eventsThe Power of NetworkingThe ROI of B2B tech eventsIf you are considering hosting a b2b tech event, sponsoring a b2b tech event or attending a b2b tech event, this episode is chalked full of insights, perspectives and the return on investment thesis to consider.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

As SaaS pricing evolves to be more variable in nature, such as in Usage-Based Pricing or Value-Based Pricing the requirements for a more flexible billing platform that also enhances the customer experience and also becomes a foundational component of financial reporting.Apurv Bansal, founder at Zenskar is converting that evolving need into a next generation billing platform. During this conversation with Apurv, our host Ray Rike covers the following topics with Apurv:The evolving nature of Usage-Based pricing and its Impact on Billing Software RequirementsThe role of customer experience in billing -Revenue Management - beyond manual processes and platformsRevenue Operations - The impact of Billing PlatformsRecent benchmarking research indicates that over 50% of B2B SaaS companies are leveraging some level of variable pricing, such as Usage-Based Pricing and Value-Based Pricing. If a company's billing is not based upon a flat-rate subscription model, such as a "seat-based" model, the vendor knows the # users BEFORE the next months or years invoice is being calculated - because it is based upon the contact.In a Usage-Based Pricing model - the number of units required to create the bill/invoice needs to come from both the agreement and the "store of usage". This adds a significant level of nuance and complexity to the next generation of SaaS billing.When monthly invoicing is highly variable and dependent the latest usage - not only is calculating the monthly charges become more complex - the customer now needs a more detailed "customer usage report", which may also may need to be provided by user, by system or by whatever triggers a usage based trigger leading to a charge.If you are currently using or considering introducing a highly variable pricing model, and are considering both the infrastructure and the customer experience resulting from monthly invoices which vary materially based upon usage - this conversation is a highly informative and educational on the evolution of pricing models and the resultant billing technology required.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

As B2B SaaS companies scale beyond $20M the complexity of their internal process, systems and SaaS metrics calculations become much more complex. As companies begin to consider a next round of financing and/or evaluate the strategic acquisition option, being able to quickly and reliably provide potential investors the metrics that matter to them is a key factor in how investors will determine not only the "if they will invest" but also "what the enterprise value" is.During this episode, Ray discusses the below topics with J.T. Cecchini, CEO of LevelUp Finance:SaaS Reporting RoadMap5x5 Reporting MatrixLevelUp Finance Valuation FrameworkA Reporting ScoreCardIf you are a CEO, CFO or Revenue Operations leader who is responsible for ensuring the financial reporting and metrics infrastructure, data and processes are ready to scale and stand up to the scrutiny of potential investors, this episode is a great listen!!!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.