

Metrics that Measure Up
Ray Rike
B2B SaaS and Cloud founders, CEOs, and Go-To-Market operating executives share their journey as they scaled their business from $0M ARR to $100M and beyond. The guests share their insights on measurements of success, performance metrics, and benchmarks they use to guide and inform their decision-making and growth journey.Guests include founders and CEOs of amazing success stories such as LinkedIn, DocuSign, Marketo, Gainsight, Salesforce Commerce Cloud, ringDNA, InsightSquared, Cloudera and Gong. Beyond founders and CEOs, we also speak with leading Venture Capitalists, Go-To-Market executives and industry thought leaders who share their experience and insights into customer acquisition, customer retention, and customer expansion best practices.
Episodes
Mentioned books

Aug 19, 2025 • 29min
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 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.

Aug 15, 2025 • 34min
Real-time Data-Driven Insights and Decisions - with Josh Schauer, CFO insightsoftware
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.

Jul 17, 2025 • 32min
The Scaler Role, Personality Traits and Business Impact - with Casey Woo, Founder and CEO Operators Guild
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.

Jul 11, 2025 • 37min
Future of FP&A + AI - with Melissa Howatson, CFO Vena Solutions
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.

Jul 2, 2025 • 39min
B2B SaaS and AI-Native Pricing Frameworks - with Marcos Rivera, Founder and CEO Pricing I/O
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.

Jun 18, 2025 • 33min
Integrating GTM in a PLG Company - with Shane Murphy-Reuter, President GTM Calendly
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.

Jun 11, 2025 • 30min
The Role of the Fractional CFO - with Josh Aharonoff, Your CFO Guy and Founder Mighty Digits
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.

Jun 4, 2025 • 32min
Revenue Recognition in B2B SaaS and Native-AI has never been harder - with Dan Miller, CFO RightRev
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.

May 23, 2025 • 32min
Measuring and Forecasting Marketing ROI - with Pranav Piyush, Founder and CEO Paramark
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.

May 16, 2025 • 32min
B2B Marketing and AI trends with Sydney Sloan - Chief Marketing Officer at G2
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.