Run the Numbers

CJ Gustafson
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10 snips
Jan 29, 2026 • 47min

The CFO Rule for AI Forecasting: “It’s Not Zero” | Dan Griggs

Dan Griggs, CFO of Intercom who led its AI pivot and launched the Fin product, shares practical finance rules for AI-era decision making. He explains the “it’s not zero” forecasting mindset. Short takes cover pricing Fin at $0.99 per resolution, unit economics, model selection to cut costs, scenario planning, and handling potential cannibalization while scaling AI.
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5 snips
Jan 26, 2026 • 53min

How finance shows its value beyond being the “no” department | Maria Izurieta

Maria Izurieta, CFO of Huntress who builds people-first, scalable finance functions across VC, PE, and public companies. She talks about finance as connective tissue in organizations. Short wins build trust. Data transparency and centralized BI turn disputes into strategy. CFOs partnering with revenue teams unlock predictability and margin-aware deal-making.
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8 snips
Jan 22, 2026 • 55min

How the Best CFOs Lead Without Being the CEO | Ken Stillwell

Ken Stillwell, CFO and COO of Pegasystems, is a seasoned leader in finance and operational transformations. He discusses the nuances of supporting a CEO while providing directional clarity and trust in sales compensation changes. Ken highlights the risks of KPI obsession, advocating for a focus on meaningful metrics instead. He also compares private equity's discipline with public market challenges, reflecting on Pega's strategic shift to cloud and subscription models. His candid insights on communication and adapting goals to various teams round out this enlightening conversation.
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7 snips
Jan 19, 2026 • 50min

How Finance Becomes a GTM Partner, Not a Bottleneck | Chris Brubaker

In this engaging discussion, Chris Brubaker, SVP of Finance at Postscript, shares his insights on transforming finance into a collaborative partner for go-to-market teams. He emphasizes the importance of establishing deal desks early and setting pricing guardrails based on data analysis. Chris showcases innovative automation strategies using AI, like a Slack bot streamlining deal processes. He touches on evolving metrics for forecasting and the critical balance between internal data and benchmarks. Plus, he shares a lighthearted private jet accounting story!
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21 snips
Jan 15, 2026 • 53min

The CFO Case for Probabilistic Forecasting With AI | Bruno Annicq

Bruno Annicq, CFO of Wellhub and former consultant at McKinsey and AOL, shares insights on reshaping finance with AI-driven probabilistic forecasting. He contrasts traditional forecasting with a more flexible, ensemble model, dramatically improving accuracy. Bruno discusses his EMPOWER planning framework, emphasizing transparency and joint OKRs to align finance and HR for better employee well-being. He also highlights the importance of cash discipline for sustainable growth, positioning finance as a strategic partner in employee health and company performance.
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33 snips
Jan 12, 2026 • 57min

Automation Outside the Tech Bubble | Jason Kong

In this conversation, Jason Kong, General Partner at Base10 Ventures, reveals insights into 'automation for the real economy,' focusing on software solutions for often overlooked industries. He discusses the challenges of Series B investing and why the real economy is underserved by tech investors. Jason also highlights Base10's unique model of donating 50% of profits for scholarships, fostering meaningful founder relationships. He shares lessons from hedge funds, such as avoiding echo chambers, and wraps up with a quickfire session covering topics from IPO chaos to fantasy football.
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Jan 8, 2026 • 1h 3min

Scaling to $1B+ Revenue: From ServiceNow to Samsara | Dominic Phillips

Dominic Phillips, CFO of Samsara, has navigated the company through hypergrowth, a tough down round during COVID, and a successful IPO in 2021. He discusses his journey from ServiceNow, emphasizing lessons in capital allocation and investor education. The conversation highlights Samsara's innovative IoT solutions, the importance of clear ROI in operations software, and the challenges of selling into non-discretionary budgets. Dominic also shares insights on building credibility with analysts and the strategic nuances of managing investor expectations.
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Jan 5, 2026 • 57min

Hackers and Hidden Risks: Business Insurance Breakdown with Gordon Coyle

Gordon Coyle, a 40-year veteran in commercial insurance and principal of The Coyle Group, shares invaluable insights into business insurance for startups. He explains the rising pressure from investors for D&O coverage and why founders often misunderstand critical components of policies. Gordon elaborates on the complexities of E&O and cyber coverage, underscoring the importance of having robust response resources. Additionally, he offers advice on balancing budget and risk tolerance, emphasizing the need for experienced brokers in navigating these waters.
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Jan 1, 2026 • 49min

a16z’s Alex Immerman on How AI Is Redefining the Modern CFO | Mostly Classics

In this conversation, Alex Immerman, a partner at Andreessen Horowitz specializing in fintech, discusses the evolving role of CFOs in the AI era. He highlights key traits of successful CFOs, such as strategic thinking and founder-like energy. Immerman emphasizes the necessity of AI deployment in internal processes and the importance of addressing investor concerns candidly. He also contrasts financial metrics between AI-native and traditional companies, stressing the significance of LTV to CAC and the changing landscape of IPO readiness.
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Dec 29, 2025 • 1h 4min

The Strategic Power of Investor Relations | Mostly Classics

In this insightful discussion, investor relations experts Samuel Levenson and Jon Neitzell dive into the strategic role of IR in aligning communication with business goals. Levenson emphasizes the importance of targeting the right investors and tailoring messages based on different investor types. Neitzell shares how data-driven insights can avoid poor capital allocation decisions and improve investor confidence. They also explore adapting IR strategies for algorithmic trading, highlighting the blend of metrics with compelling narratives.

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