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Ep 28: How Planning Aces Are Made

Planning Aces

Release Date: 10/27/2023

Ep 50: Discipline at the Heart of Innovation show art Ep 50: Discipline at the Heart of Innovation

Planning Aces

In this episode of Planning Aces, we spotlight FP&A insights from three CFOs leading innovation with discipline: Chris Sands (InvoiceCloud), Steve Sutter (Celigo), and Niels Boon (Cint). Each shares how finance is shaping AI, go-to-market models, and data-driven transformation without losing rigor. From building an “AI Ops” function and embedding finance in sales strategy, to piloting AI tools in small, staged experiments, these leaders treat innovation as a managed process. Our resident thought leader joins to connect the dots, emphasizing structure, clear metrics,...

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Ep 49: AI's Early Returns show art Ep 49: AI's Early Returns

Planning Aces

In this episode of Planning Aces, host Jack Sweeney and resident thought leader Brett Knowles explore how finance leaders are approaching AI’s early returns—balancing efficiency, experimentation, and human judgment. CFO Craig Foster of Pax8 discusses how AI enablement is driving measurable productivity gains. CFO David Obstler of Datadog reflects on finding ROI amid rapid innovation and market demand. And CFO Ben Gammell of Brex shares why forecasting still requires human intuition despite data-driven progress. Together, their insights reveal a spectrum of FP&A strategies defining...

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Ep 48: Finance Leaders Decode AI's Promise show art Ep 48: Finance Leaders Decode AI's Promise

Planning Aces

In this Planning Aces special, three finance leaders map how AI is moving FP&A from dashboards to decisions. Andrew Casey (Amplitude) shows agents automating analytics, experiments, and order-to-cash checks to democratize insight and speed action. Eric Brown (Cohesity) contrasts AI’s capital intensity with the cloud era and spotlights an “epic data battle” where privileged datasets drive advantage. Chris Miorin (APEX Analytix) links on-prem investment and clean data to faster product velocity. Co-host Brett Knowles ties it together: avoid AI-washing; structure data; target...

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Ep 47: The Prove-It Mentality: Rethinking ROI in the Age of AI show art Ep 47: The Prove-It Mentality: Rethinking ROI in the Age of AI

Planning Aces

In Episode 47 of Planning Aces, Jack Sweeney and resident thought leader Brett Knowles explore the evolving role of FP&A through the lens of three forward-looking CFOs. Dan Zhang (ClickUp), John Rettig (Bill), and Josh Schauer (insightsoftware) share how they’re driving enterprise agility, leveraging AI to eliminate inefficiencies, and rethinking capital allocation. From Zhang’s battle against “SaaS overload” to Rettig’s “prove-it mentality” and Schauer’s daily forecasting, each CFO reveals a distinct approach to enabling smarter, faster decision-making. Their insights...

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Ep 46: From Flailing to AI Forward Motion show art Ep 46: From Flailing to AI Forward Motion

Planning Aces

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Ep 45: Redefining Efficiency: The Three Dimensions of AI ROI show art Ep 45: Redefining Efficiency: The Three Dimensions of AI ROI

Planning Aces

In this episode of Planning Aces, co-hosts Jack Sweeney and Brett Knowles spotlight the FP&A strategies and AI adoption journeys of three CFOs—Jillian Munson (Vimeo), Dan Fletcher (Planful), and Chad Gold (FullStory). Each finance leader discusses how AI is reshaping their planning processes, from accelerating automation and revenue generation to transforming cross-functional collaboration. Brett introduces a framework for evaluating AI ROI across three dimensions: operating cost reduction, risk mitigation, and revenue generation. The episode reveals how FP&A teams are becoming...

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Ep 44: Built for Turbulence: Finance Planning in Motion show art Ep 44: Built for Turbulence: Finance Planning in Motion

Planning Aces

This Planning Aces episode explores how finance leaders navigate volatility without drifting into political cross‑currents like tariffs. Prologis CFO Tim Arndt explains why e‑commerce triples warehouse demand and how real‑estate strategies must adapt. Genworth CFO Jerome Upton shows how disciplined leverage and balanced product exposure turn rate uncertainty into opportunity while guarding against inflationary claim spikes. Flexport CFO Stuart Leung reveals the weekly two‑hour operating cadence and scenario drills that keep freight flows nimble amid strikes, conflicts, and...

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Ep 43: The ROI Equation for AI Starts Here  show art Ep 43: The ROI Equation for AI Starts Here

Planning Aces

In this episode of Planning Aces, three forward-looking finance leaders share how they’re transforming planning and forecasting inside their organizations. CFO Kevin Rhodes of Extreme Networks discusses the dual lens through which he evaluates AI—external monetization and internal productivity. Brendon Sullivan, CFO of 2X, reveals how a post-PE investment reality check led him to pioneer a weekly reporting cadence to drive faster decision-making. Meanwhile, Gabi Gantus of Mytra AI draws on her Tesla FP&A roots to illustrate how finance can lead long-term operational planning. Brett...

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Ep 42: From Misaligned Commissions to Unified Goals show art Ep 42: From Misaligned Commissions to Unified Goals

Planning Aces

In our latest Planning Aces episode of CFO Thought Leader, Jack Sweeney teams with FP&A veteran Brett Knowles to spotlight three finance leaders tackling one of business’s most critical challenges: aligning sales, operations, and finance around a common goal. First, Orion Innovation CFO Cyrus Lam recalls how transparent metrics and well-crafted incentives helped double profit margins by bridging the gap between sales and delivery teams. Then, Jellyfish CFO Joanne Cheng reveals the power of being a “connector”—a finance leader who unifies fast-scaling startups by integrating hires,...

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Ep 41: The FP&A Spectrum: Technology, Culture, and Long-Term Value show art Ep 41: The FP&A Spectrum: Technology, Culture, and Long-Term Value

Planning Aces

In this episode of Planning Aces, co-hosts Jack Sweeney and Brett Knowles explore insights from CFOs Sandra Wallach (Amprius Technologies), David Morris (Guardian Pharmacy Services), and David Eckstein (Vanta). The discussion highlights themes around technology adoption and data-driven decision-making. Sandra Wallach emphasizes the importance of hands-on involvement, leveraging weekly meetings and direct collaboration to stay aligned with supply chain and customer needs. David Morris reflects on Guardian's long-term journey to IPO, underscoring rigorous planning processes, investment in data...

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More Episodes

This episode features insights and commentary from three finance leaders: CFO Michael Linford of Affirm, CFO Ana Chadwick of Pitney Bowse, and CFO Jason Leet of Zylo.

Imagine if these three finance leaders were to meet and have a discussion about their past roles. Each of them has a unique story to tell. Michael Linford, for example, was previously part of HP's M&A integration group and later became the first CFO of Hewlett Packard Enterprise after the split-off. Anna Chadwick played a key role in GE Capital's divestiture chapter, overseeing more than 50 divestitures globally. Jason Leet, on the other hand, has extensive experience in M&A, having been involved in over 40 different acquisitions during his time at Salesforce and Exact Target.