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.