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Metrics that Measure Up

Author: Ray Rike

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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.


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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.
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