
Advertise on podcast: AI to ROI (fka Metrics that Measure Up)
Rating
4.9from
This podcast has
220 episodes
Language
EnglishPublisher
Ray RikeExplicit
No
Date created
2020/07/29
Latest episode
2026/02/04
Average duration
32 min.
Release period
20 days
Description
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. AI to ROI is the evolution of the original "Metrics to Measure Up" podcast for the AI era.
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Check latest episodes from AI to ROI (fka Metrics that Measure Up) podcast
Measuring the performance and business impact of AI agents - with Todd Olson, Founder and CEO Pendo
2026/02/04
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.
The Strategic Future of FP&A - with Albert Gozzi, Founder and CEO Aleph
2025/10/08
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.
The Use and ROI of AI in Finance - with Sowmya Ranganathan, Former Controller OpenAI and CEO, Lumera
2025/10/01
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.
The Role of FP&A in Business Strategy - with Christina Ross, Founder and CEO Cube
2025/09/18
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.
Exit Ready Analytics - with Will Sullivan, Managing Partner at Predictive Analytics
2025/08/19
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.
Real-time Data-Driven Insights and Decisions - with Josh Schauer, CFO insightsoftware
2025/08/15
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 insights
If 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.
The Scaler Role, Personality Traits and Business Impact - with Casey Woo, Founder and CEO Operators Guild
2025/07/17
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 scalers
If 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.
Future of FP&A + AI - with Melissa Howatson, CFO Vena Solutions
2025/07/11
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 podcast
The 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.
B2B SaaS and AI-Native Pricing Frameworks - with Marcos Rivera, Founder and CEO Pricing I/O
2025/07/02
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 frameworks
Marco 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 optimization
Another key topic discussed was the 9 psychological concepts for pricing, including:
Halo effectLoss aversion (FOMO)Social proofConfirmation biasScarcity effectMere exposure effectAnchoring effectAuthority biasGoal gradient effect
If 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.
Integrating GTM in a PLG Company - with Shane Murphy-Reuter, President GTM Calendly
2025/06/18
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 company
One 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.
The Role of the Fractional CFO - with Josh Aharonoff, Your CFO Guy and Founder Mighty Digits
2025/06/11
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 process
If 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.
Revenue Recognition in B2B SaaS and Native-AI has never been harder - with Dan Miller, CFO RightRev
2025/06/04
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 Pricing
If 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.
Measuring and Forecasting Marketing ROI - with Pranav Piyush, Founder and CEO Paramark
2025/05/23
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 CFO
If 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 with Sydney Sloan - Chief Marketing Officer at G2
2025/05/16
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 Marketers
If 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 Intelligence Market in 2025 - with Ben Eisenberg, CEO People Data Labs
2025/05/08
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 years
If 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.
Podcast reviews
Read AI to ROI (fka Metrics that Measure Up) podcast reviews
PeteSteg 2024/03/04
If metrics matter to you, listen to this show
If you’re a SaaS leader, then metrics are important to you - and this show is a great place to stay up-to-date on the latest trends and up your game o...
mvelasco07 2023/02/03
Great podcast!
Can’t believe an incredibly valuable resource like this podcast is FREE! 🤩
No matter the subject, you’re guaranteed to gain something from Ray and ...
Bluesky13579 2022/10/23
Must listen for SaaS professionals!
Great content!
McQuillen.56 2021/12/19
A required podcast for all associates in the firm
We have started to aggressively look to make more investments in B2B SaaS and Cloud companies and needed a base level primer on metrics for the indust...
Miguel.131 2021/12/19
Why have I not heard of this podcast before?
I listen to the SaaStr and Masters of Scale podcasts, and thought those were enough B2B SaaS podcasts - so happy I stumbled onto this one when I was t...
Moshe611 2021/12/19
Great podcast - highly recomme
Every day I am dealing with new areas and topics that I have not personally been responsible. Ray's guests have a wide variety of experiences that ra...
Guerrilla999 2021/08/21
Great content, great interviewer
Ray is a phenomenal interviewer. You can tell that he prepares well for each interview, and he has a knack for asking the right questions to get great...
maxcfo 2021/01/23
Great SaaS podcast
Ray has great guests and valuable insights for founders, executives, and investors alike. Engaging and fun to listen to.
twihasa 2021/01/11
Great insight
Rays attention to detail and his network of top sales leaders guarantees value in every episode.
Pete Hurtubise 2021/01/11
SaaS Professionals
This is great podcast for SaaS sales, marketing, product and leadership teams!
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