AI to ROI

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.

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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 Aleph
• The evolution of AI in FP&A
• FP&A’s role in developing corporate strategy
• Growth 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!

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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 OpenAI
• Challenges in one of the fastest growing software companies of all time
• Understanding compute expenses is critical to understanding the financial performance today and tomorrow at an AI company
• Why 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 data
• Why historic analysis is not a good place to start for forecasting in a hypergrowth, compute intensive company
• Leveraging AI in the Financial close process - leveraging data warehouse information to build a repeatable process
• Tracking GPU costs in real-time throughout the month - not an excel scale requirement
• Hallucinations are a real concern - but once your AI is encapsulated as standard code - the concerns are minimized
• Human 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!!!

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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&A
• The biggest challenges facing CFOs with the FP&A function today
• The role of FP&A in business strategy
• The 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!

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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 how
• The differences between a strategic Chief Revenue Officer and a Head of Sales
• When to hire a CRO and their responsibilities
• How 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!

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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-making
• Moving from historic to real-time data for Financial decision-making
• Developing a process to quickly integrate acquired companies into your financial systems
• Modifying 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!!!

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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!!!

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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!!!

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