AI to ROI

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 co...

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 t...

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 i...

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 an...

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...

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...

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 transaction...

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, operat...

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. Dur...

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&A AI in Finance - the importance of...

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 strategy 9 psychology concepts for pricing Differences between SaaS and AI pricing The value of pricing frameworks Marco wa...

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 ac...

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...

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 tre...

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. Para...

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 2025 Peer reviews and their impact on B2B SaaS purchases The growth in AI - a...

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 h...

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 experien...

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 CRO The catalyst for transitioning to an "inbound GTM motion" The...

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, Monevate During our conversation we covered four primary topics with James: Actual Value versus Perceived Value - which matters most Price Metric Evaluation Criteria Innovative Monetization Strateg...

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...

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...

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...

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 co...

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...