Speaking C-Suite

Johnnie Walker
  • 5.0 (1)
  • Technology

Speaking C-Suite is a podcast series that dives into the high-stakes conversations between CFOs and other key executives at scaling startups and growth-stage companies. As businesses mature, the role of the CFO becomes increasingly strategic—focused not only on financial oversight, but also on integrating data across teams, driving operational efficiency, and enabling smarter, faster decision-making. Each episode explores how modern CFOs leverage advanced analytics, scalable tech platforms and cross-functional collaboration to solve real challenges—from optimizing sales performance to building out data infrastructure and managing complex compensation planning.

Episodes

  1. 2d ago

    Andrew Rea & Aman Samra Speak C-Suite

    In this episode of Speaking C-Suite, hosts Johnnie Walker (Rooled) and David Hemenway (The Angel Nest) sit down with Andrew Rea, founder and CEO of Taxwire, and Aman Samra, VP of Finance at Spellbook, to talk through how growing companies handle sales tax compliance across thousands of jurisdictions. Andrew traces the shift back to the 2018 Supreme Court ruling that removed the physical presence requirement for sales tax, combined with remote hiring creating nexus in new states and software increasingly becoming taxable. California will start taxing software for the first time starting January 1. Taxwire now files and remits around $100 million a year in sales tax for its customers, pairing a tax engine with an in-house research team of four people covering roughly a dozen industries. Aman shares how he evaluates compliance vendors as Spellbook scaled from the Canadian and US markets to over 100 countries in three years. He set a $10 million ARR threshold for bringing in a dedicated sales tax platform, and explains why he passed on vendors charging a percentage of revenue in favor of a flat, predictable cost. The conversation also covers Taxwire's free nexus exposure tool for accounting firm partners like Rooled, letting controllers flag a client's exposure before it becomes a problem. Key topics include: The 2018 Supreme Court ruling that changed how sales tax nexus worksWhy software taxability is expanding state by stateSetting a revenue threshold for when to bring in a compliance platformEvaluating vendors on service model instead of percentage-of-revenue pricingHow large language models are used to structure tax law into a rules engineBuilding a tax research team that supports a dozen industriesUsing a free nexus tool to catch exposure before it becomes historical liabilityAndrew Rea's path from Columbus, Ohio to founding Taxwire Speaking C-Suite is supported by Aleph, Rillet, Tabs, and Taxwire. This episode also features Taxwire's own founder as a guest. Thank you for helping make this series possible. Subscribe on YouTube and follow Speaking C-Suite for conversations with operators shaping the future of finance and growth.

    Andrew Rea & Aman Samra Speak C-Suite

  2. Aug 31

    Jim Cook Speaks C-Suite

    In this episode of Speaking C-Suite, hosts Johnnie Walker (Rooled) and David Hemenway (The Angel Nest) sit down with Jim Cook, a founding team member at Netflix and an early finance hire at both Intuit and Mozilla, to talk about building a finance function from the first hire through a thousand employees. Jim traces his approach to systems back to Quicken, which shipped without any budgeting feature for its first two years. He walks through why budgeting isn't the earliest system a company needs, and describes the lesson he learned touring a 200,000-square-foot postal warehouse before Netflix designed its first shipping envelope. That experience shaped his view of the CFO as the hub connecting every department's activity back to the numbers. The conversation covers his argument that ERPs are giving way to a shared data layer where AI agents function like today's version of pivot tables and Excel macros, Dunbar's number and the specific headcount points where company structure breaks down, the office strategy that took Mozilla from roughly 25 employees to 1,100 across twelve countries, and how he brought in outside treasury experts once the balance sheet crossed $500 million. Key topics include: Why budgeting isn't the first system a startup needsBuilding systems that remove friction for the rest of the teamHow touring a postal warehouse shaped Jim's view of the CFO roleThe CFO scorecard he built for tracking growthWhy ERPs are giving way to a shared data layer for AI agentsDunbar's number and the headcount points where companies breakBringing in outside experts to manage treasury risk at scaleCommunicating with boards by asking questions instead of making statements Speaking C-Suite is supported by Aleph, Rillet, Tabs, and Taxwire. Thank you for helping make this series possible. Subscribe on YouTube and follow Speaking C-Suite for conversations with operators shaping the future of finance and growth.

    Jim Cook Speaks C-Suite

  3. Apr 27

    David Johnson & Johnnie Walker Speak C-Suite

    In this episode of Speaking C-Suite, host David Hemenway (The Angel Nest) turns the mic on his co-hosts — Johnnie Walker and David "DJ" Johnson, the co-founders of Rooled, the outsourced finance firm serving founders and VC-backed companies across accounting, CFO advisory, and tax, and the pioneering sponsor behind this podcast series. DJ and Johnnie pull back the curtain on what it actually takes to build an outsourced finance company from the ground up — from the early days of Temp CFO in the late '90s, when startups couldn't produce a financial statement to save their lives, to building Rooled into a 30-person, tech-enabled firm trusted by companies like Stripe, Slack, and Pinterest. The conversation gets into the unglamorous but critical realities of startup finance: revenue recognition mistakes founders don't know they're making, fraud uncovered on the job, why clients stay longer than ever (and which ones get fired), and how AI is reshaping the transactional work without replacing the human judgment that actually matters. DJ and Johnnie also share what the next five to seven years look like for outsourced finance — and why firms that invest in technology and people will come out ahead. Whether you're a founder trying to get your books right before your next raise, a CFO curious about where the industry is heading, or an operator who wants to understand what separates good financial infrastructure from a house of cards — this episode is a grounded, candid look at the finance function most people overlook until it's too late. Key topics include: Why outsourced finance took off — and what really drove its growthThe most common structural mistakes founders make in the early stagesRevenue recognition: why founders almost always get it wrong at firstReal stories of financial fraud uncovered inside VC-backed companiesHow AI is changing transactional accounting — and what it can't replaceWhy Rooled fires clients (and how they spot the red flags early)The team-first culture behind Rooled's long client and staff retentionWhat outsourced finance looks like in five to seven years Speaking C-Suite is proudly supported by Aleph, Tabs, and Rillet — thank you for helping make this series possible! Subscribe on YouTube and follow Speaking C-Suite for more conversations with operators shaping the future of finance and growth.

    David Johnson & Johnnie Walker Speak C-Suite

  4. Jan 20

    Katie Royce Speaks C-Suite

    In this episode of Speaking C-Suite, hosts Johnnie Walker (Rooled) and David Hemenway (The Angel Nest) sit down with Katie Royce, Chief Financial Officer at ZenBusiness, to break down how modern finance leaders build scalable operations, evaluate tech platforms, and turn finance into a strategic growth engine — not just a reporting function. Katie shares an inside look at how she helped transform ZenBusiness into a subscription-first, tech-enabled platform serving nearly one million entrepreneurs. She explains why great CFOs don’t just communicate numbers — they provide context — helping teams, boards, and product leaders “see around corners” and make smarter decisions. The conversation dives into how emerging finance tools are evaluated, how to balance customization versus scale, why “boring infrastructure wins,” and what it really takes to drive adoption across cross-functional teams. Katie also discusses where AI is genuinely delivering ROI today (and where it isn’t), how to think about data privacy in a shifting tool landscape, and why judgment will always remain a competitive advantage for finance leaders. Whether you’re a CFO, FP&A leader, founder, or operator, this episode offers a grounded, experience-driven playbook for building a modern finance function that informs product, accelerates strategy, and scales without adding unnecessary headcount. Key topics include: How to evaluate finance tech platforms without getting lost in edge cases When rigidity in product strategy becomes a scaling advantage The hidden cost of implementations: change management vs. configuration Why adoption determines ROI — not just feature lists Where AI is delivering real productivity gains in finance today Data security and privacy considerations for AI-enabled platforms How to build high-leverage finance teams and identify SME hires Why context (not reporting) defines modern CFO leadership Speaking C-Suite is proudly supported by Aleph, Tabs, and Rillet — thank you for helping make this series possible! Subscribe on YouTube and follow Speaking C-Suite for more conversations with operators shaping the future of finance and growth.

    Katie Royce Speaks C-Suite

  5. 12/22/2025

    Harini Gokul Speaks C-Suite

    Customer success has become one of the most powerful drivers of sustainable growth. In this episode of Speaking C-Suite, hosts David Hemenway and Johnnie Walker sit down with Harini Gokul, Chief Customer Officer at Entrust, to explore how modern customer success organizations fuel retention, expansion, and predictable revenue. Harini breaks down the shift from customer service to customer-centric growth, sharing how customer success teams partner with CFOs to de-risk recurring revenue, improve forecasting, and drive expansion within the installed base. She explains why adoption and value realization are the strongest leading indicators of retention, and how data, telemetry, and AI are reshaping post-sales strategy. This episode is essential listening for CFOs, founders, CCOs, and revenue leaders building efficient growth in subscription and consumption-based business models. Key topics include: Customer success as a revenue and growth strategyRetention, expansion, and churn in SaaS and enterprise businessesHow CFOs evaluate customer success investmentsMeasuring customer adoption and usageThe role of AI in modern customer success teams Speaking C-Suite is proudly supported by Aleph, Tabs, and Rillet.

    Harini Gokul Speaks C-Suite

  6. 12/01/2025

    Jocelyn Goldfein Speaks C-Suite

    In this episode, we sit down with Jocelyn Goldfein, Managing Director at Zetta Venture Partners, former engineering leader at Facebook and VMware, and one of the most respected voices in AI-driven innovation. Jocelyn offers a candid look into how today’s leaders evaluate AI opportunities, why project selection determines 80% of success, and what executives get wrong when adopting emerging technologies. From identifying tractable use cases to building for real ROI, Jocelyn breaks down the frameworks every CFO, CTO, and operator needs to ensure their AI investments create meaningful business impact—not just impressive demos. Whether you're navigating early experimentation or scaling AI across the enterprise, this conversation delivers the clarity modern leaders need to make confident strategic decisions. Key TakeawaysProject selection is the make-or-break factor in AI success — most failures stem from choosing problems that are too high-stakes or too low-impact.“Toy problems” kill momentum — even technically successful AI builds won’t get deployed if they don’t deliver value.Successful AI adoption requires cross-functional ownership — CFOs and technical leaders must align on resources, constraints, and business outcomes.The AI frontier is accelerating scientific innovation — many recent Nobel-adjacent breakthroughs have leveraged AI to expand the boundaries of discovery.Experimentation is essential, but it must be purposeful — companies need intentional guardrails to avoid wasted cycles and stalled pilots.

    Jocelyn Goldfein Speaks C-Suite

  7. 11/03/2025

    Kiran Hebbar Speaks C-Suite

    In Episode 2, we’re joined by Kiran Hebbar, Chief Financial Officer at Alloy, the leading identity decisioning and fraud prevention platform serving over 750 financial institutions and fintechs. Kiran brings a uniquely well-rounded perspective—blending experience as a CFO, venture investor, and engineer. Before Alloy, he served as CFO at mParticle and spent a decade as General Partner at Valhalla Partners, investing in early-stage B2B SaaS companies. Kiran sits down with hosts Johnnie Walker (Rooled) and David Hemenway (The Angel Nest Podcast) to explore: -How Kiran’s venture background shaped his approach to operational strategy and investor relations. -How Alloy’s leadership turned a CEO’s mission into measurable strategic pillars and financial targets. -Lessons in scaling a usage-based model and defining metrics that matter. -How Alloy is innovating with AI-driven fraud detection and balancing automation with customer experience. -Why modern CFOs must master sales, marketing, and product fluency to drive enterprise value. -The communication, forecasting, and data discipline every CFO needs to inspire investor confidence.

    Kiran Hebbar Speaks C-Suite

  8. 09/03/2025

    Cassie Young Speaks C-Suite

    Cassie Young, General Partner at Primary Venture Partners, sits down with Johnnie Walker, co-founder of Rooled, and David Hemenway, host of the Angel Nest to Speak C-Suite.

    Cassie Young Speaks C-Suite
  • 8 Episodes

About

Speaking C-Suite is a podcast series that dives into the high-stakes conversations between CFOs and other key executives at scaling startups and growth-stage companies. As businesses mature, the role of the CFO becomes increasingly strategic—focused not only on financial oversight, but also on integrating data across teams, driving operational efficiency, and enabling smarter, faster decision-making. Each episode explores how modern CFOs leverage advanced analytics, scalable tech platforms and cross-functional collaboration to solve real challenges—from optimizing sales performance to building out data infrastructure and managing complex compensation planning.

Information

  • Creator
    Johnnie Walker
  • Years Active
    2025 - 2026
  • Episodes
    8
  • Rating
    Clean
  • Copyright
    © Copyright 2025 Rooled, Inc.
  • Show Website
    Speaking C-Suite