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 business
• The personality traits of a scaler
• How process and performance interact from a scaler's perspective
• How 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.

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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 change management
• Metrics that Matter at > $100M ARR
• Measuring 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.

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 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 delivers
• Establish a clear market position
• Pricing that builds trust
• Case studies and ROI proof
• Have a pricing point of view
• Consistent pricing messaging
• Data-Driven pricing insights
• Social proof and testimonials
• Ongoing price optimization

Another key topic discussed was the 9 psychological concepts for pricing, including:

• Halo effect
• Loss aversion (FOMO)
• Social proof
• Confirmation bias
• Scarcity effect
• Mere exposure effect
• Anchoring effect
• Authority bias
• Goal 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!!!

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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 Company
• The key inflection points in scaling a PLG company
• How 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.

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 CFO
• When to consider an internal VP Finance or CFO
• Why excel is a CFOs best friend…or NOT
• Building 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.

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 recognition
• How does the evolution of Outcome-Based pricing impact revenue recognition
• How AI is and will impact the Office of Finance

A 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 reporting
• Blended offerings including a fixed fee + usage are great for customers - but hard to manage revenue recognition
• How token and credit-based pricing impacts revenue recognition and gross profit calculation and reporting
• The 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.

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 CFO
• The concept of incrementality
• How to anticipate and measure channel specific diminishing returns
• Brand vs Performance measurements
• The 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 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 - as measured by categories and vendors with G2 reviews
• The 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 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 Service
• How will next generation Data Intelligence solutions address the current challenges
• Ben’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.

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 company
• The lessons learned in transitioning from a perpetual license to a B2B SaaS subscription model
• The preparation required to take a B2B SaaS company public
• How technology has changed the Office of Finance and the CFO role
• The journey to becoming a B2B SaaS CFO - the Bill Koefoed path

Bill 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.