AI to ROI (fka Metrics that Measure Up)

Ray Rike
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AI to ROI is a podcast that shares how enterprises translate AI investments into measurable business value. Hosted by Ray Rike, Founder and CEO of Benchmarkit, the show features senior enterprise leaders and AI software executives who share how AI initiatives move from pilots to production, and how ROI is actually measured and achieved. In addition, each week, we publish a bonus episode with AI to ROI Newsletter co-author, Peter Buchanan to discuss the Big Story of the Week. The AI to ROI podcast is the evolution of the original "Metrics to Measure Up" podcast.

  1. SaaS to AI-First Transformation

    2D AGO

    SaaS to AI-First Transformation

    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 engines The 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 growth The 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 automation A 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 lack The 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" future Advice 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.

    33 min
  2. Navigating the Shift to AI-Powered Revenue Workflows - A CFOs Perspective with Drew Laxton, CFO Outreach

    4D AGO

    Navigating the Shift to AI-Powered Revenue Workflows - A CFOs Perspective with Drew Laxton, CFO Outreach

    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.

    31 min
  3. Context Graphs - AI’s Trillion-Dollar Technology

    FEB 6

    Context Graphs - AI’s Trillion-Dollar Technology

    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 Takeaways The 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.Timestamps 00:00 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.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    25 min
  4. Measuring the performance and business impact of AI agents - with Todd Olson, Founder and CEO Pendo

    FEB 4

    Measuring the performance and business impact of AI agents - with Todd Olson, Founder and CEO Pendo

    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 enterprise Key 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.

    28 min
  5. The Strategic Future of FP&A - with Albert Gozzi, Founder and CEO Aleph

    10/08/2025

    The Strategic Future of FP&A - with Albert Gozzi, Founder and CEO Aleph

    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 category If 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.

    31 min
  6. The Use and ROI of AI in Finance - with Sowmya Ranganathan, Former Controller OpenAI and CEO, Lumera

    10/01/2025

    The Use and ROI of AI in Finance - with Sowmya Ranganathan, Former Controller OpenAI and CEO, Lumera

    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 billing A 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.

    31 min
  7. The Role of FP&A in Business Strategy - with Christina Ross, Founder and CEO Cube

    09/18/2025

    The Role of FP&A in Business Strategy - with Christina Ross, Founder and CEO Cube

    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 performance If 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.

    31 min
  8. Exit Ready Analytics - with Will Sullivan, Managing Partner at Predictive Analytics

    08/19/2025

    Exit Ready Analytics - with Will Sullivan, Managing Partner at Predictive Analytics

    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 relationship If 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.

    29 min
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About

AI to ROI is a podcast that shares how enterprises translate AI investments into measurable business value. Hosted by Ray Rike, Founder and CEO of Benchmarkit, the show features senior enterprise leaders and AI software executives who share how AI initiatives move from pilots to production, and how ROI is actually measured and achieved. In addition, each week, we publish a bonus episode with AI to ROI Newsletter co-author, Peter Buchanan to discuss the Big Story of the Week. The AI to ROI podcast is the evolution of the original "Metrics to Measure Up" podcast.

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