Speaking C-Suite

In this episode of Speaking C-Suite, hosts Johnnie Walker (Rooled) and David Hemenway (The Angel Nest) sit down with Stephen Hedlund, head of finance at Rillet, the AI-native general ledger built by accountants, and Brock Beyer, controller at JUMP, the AI operating system for financial advisors and a Rillet customer, to talk through what it takes to actually replace a company's accounting system instead of just patching it.

Rillet has grown past six hundred customers and raised more than $100 million in under a year, and Stephen explains how the company now pulls finance teams off SAP and Oracle Fusion in addition to QuickBooks. About half of Rillet's staff are CPAs, including customer success managers who write and ship production code themselves; one of them, a CPA named Ethan, builds features that go directly into the product. Brock walks through what happened when JUMP moved off QuickBooks: the company migrated its historical data in about twenty-four hours, went live, and closed its August 2025 books by September 10, compared to the four to six months his last company spent on a NetSuite implementation.

Both guests dig into where AI actually saves time day to day, from Rillet's fully automated prepaid subledger to the automations Brock built in Claude on top of Ramp and Rillet. Brock describes vibe-coding a desk management tool for JUMP that took him four to six hours the first time and less than 45 minutes once he knew what he was doing, and why he thinks finance teams should expect to fail with these tools quickly rather than avoid them. JUMP has doubled in headcount since Brock joined as its first accounting hire, and he explains why he thinks accountants have historically spent too much of their time coding transactions instead of advising the rest of the business.

Key topics include:

• How Rillet grew past six hundred customers and started pulling companies off SAP and Oracle Fusion
• Why half of Rillet's team are CPAs, including customer success managers who ship production code
• JUMP's Rillet implementation: a twenty-four-hour data migration and closed books within weeks
• How Rillet's prepaid subledger automates capitalization and amortization without manual input
• Brock's experience vibe-coding a desk management tool for JUMP in Claude
• Why Brock thinks finance teams should lean into existing automations before building their own
• What JUMP's finance team does with the time it used to spend on transaction coding

Speaking C-Suite is supported by Aleph, Rillet, Tabs, and Taxwire. Subscribe on YouTube and follow Speaking C-Suite for conversations with operators shaping the future of finance and growth.

In this episode of Speaking C-Suite, hosts Johnnie Walker (Rooled) and David Hemenway (The Angel Nest) sit down with Marshall Hawks, author of Venture Debt Deals and a two-decade veteran of venture lending who spent sixteen years at Silicon Valley Bank working with companies like Airbnb, Twitch, and Fitbit.

Marshall breaks down where venture debt gets used well: early-stage companies borrowing from venture banks right after a Series A, and later-stage companies pulling in tens or hundreds of millions from private credit firms to avoid diluting a business that's already de-risked. He walks through the Planet Labs deal he led at SVB, where debt financed satellite builds and launch costs with SpaceX and Rocket Lab instead of a dilutive growth equity round. He also covers the timing question companies get wrong (most venture debt processes run three to five months, and venture banks like to lend within six to nine months of an equity round to lean on the diligence investors already did), and a mistake he sees repeatedly: handing a venture debt deal to general counsel instead of a lawyer who does this work regularly.

The conversation also covers the fallout from Silicon Valley Bank's 2023 collapse, now operating as part of First Citizens Bank and set to retire the SVB name entirely by the end of this year, and how HSBC, Stifel, and JPMorgan absorbed SVB alumni to build out their own venture lending practices. Marshall explains that trust and relationship quality, more than any number on a spreadsheet, decide whether a lender grants flexibility when something in the business goes sideways.

Key topics include:

• Where venture debt works: Series A companies borrowing from venture banks versus Series C-plus companies using private credit
• How the Planet Labs deal used debt to fund satellite builds and launch costs without a dilutive equity round
• Why venture banks want to lend within six to nine months of an equity round
• The general counsel mistake that slows down and inflates the cost of venture debt deals
• What happened to Silicon Valley Bank after 2023 and its move to the First Citizens name
• How trust and relationship quality drive a lender's willingness to grant flexibility
• Why founders should tell their lender what they're building instead of waiting to be asked

Speaking C-Suite is supported by Aleph, Rillet, Tabs, and Taxwire. Subscribe on YouTube and follow Speaking C-Suite for conversations with operators shaping the future of finance and growth.

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 works
• Why software taxability is expanding state by state
• Setting a revenue threshold for when to bring in a compliance platform
• Evaluating vendors on service model instead of percentage-of-revenue pricing
• How large language models are used to structure tax law into a rules engine
• Building a tax research team that supports a dozen industries
• Using a free nexus tool to catch exposure before it becomes historical liability
• Andrew 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.

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 needs
• Building systems that remove friction for the rest of the team
• How touring a postal warehouse shaped Jim's view of the CFO role
• The CFO scorecard he built for tracking growth
• Why ERPs are giving way to a shared data layer for AI agents
• Dunbar's number and the headcount points where companies break
• Bringing in outside experts to manage treasury risk at scale
• Communicating 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.

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:

1. Why outsourced finance took off — and what really drove its growth
2. The most common structural mistakes founders make in the early stages
3. Revenue recognition: why founders almost always get it wrong at first
4. Real stories of financial fraud uncovered inside VC-backed companies
5. How AI is changing transactional accounting — and what it can't replace
6. Why Rooled fires clients (and how they spot the red flags early)
7. The team-first culture behind Rooled's long client and staff retention
8. What 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.

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:

1. How to evaluate finance tech platforms without getting lost in edge cases
2. When rigidity in product strategy becomes a scaling advantage
3. The hidden cost of implementations: change management vs. configuration
4. Why adoption determines ROI — not just feature lists
5. Where AI is delivering real productivity gains in finance today
6. Data security and privacy considerations for AI-enabled platforms
7. How to build high-leverage finance teams and identify SME hires
8. 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.

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:

1. Customer success as a revenue and growth strategy
2. Retention, expansion, and churn in SaaS and enterprise businesses
3. How CFOs evaluate customer success investments
4. Measuring customer adoption and usage
5. The role of AI in modern customer success teams

Speaking C-Suite is proudly supported by Aleph, Tabs, and Rillet.

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.

• Project 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.

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.

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.