In this episode of Voices in Compliance, host Jason Thomas sits down with Ross Osborne, UK CEO of Rippling, to explore the complexities of scaling compliance functions within high-growth fintech environments. Ross shares his perspective on why compliance should be a business enabler rather than a "policing" unit and discusses the critical importance of building a "compliance culture" from the ground up.

The conversation covers the tactical realities of international expansion, the "red flags" to watch for during rapid hiring, and how to maintain a strong relationship with the regulator while moving at pace. Whether you are navigating a new license application or managing a global compliance footprint, Ross provides a roadmap for balancing commercial ambition with regulatory integrity.

Episode Timestamps:

• [00:00:15] Introduction: Jason welcomes Ross Osborne, CEO of Rippling, to discuss his extensive background in the fintech and payments space.
• [00:01:30] The Growth Friction: Ross explains how to manage the natural tension between commercial targets and compliance guardrails.
• [00:03:45] Compliance by Design: Why tech and product teams must be aligned with compliance goals from the very beginning of the development lifecycle.
• [00:06:20] Navigating Global Footprints: Tactical advice on managing different regulatory requirements across multiple jurisdictions.
• [00:09:50] Building the Right Team: The qualities Ross looks for when hiring compliance professionals who can thrive in a fast-paced environment.
• [00:13:10] The Role of Technology: How automation and AI are being utilized to streamline the "first line" of defense.
• [00:16:45] Engaging the Regulator: Why transparency and proactive communication are the foundations of a successful relationship with the FCA.
• [00:20:15] The Strategic MLRO: Shifting the perception of the MLRO role from a cost center to a value-add for the business.
• [00:24:40] Quick Fire Section: Ross reveals his favorite morning habits, his "Queen for a day" regulatory change, and his guilty pleasures.

In Episode 3 of Voices in Compliance, host Jason Thomas (Co-Founder of Alexander Barnes) is joined by Heather O'Gorman, Associate Director and Head of Digital Assets at FSCOM. Heather brings over a decade of experience to a deep-dive conversation on the rapidly evolving world of payments, e-money, and crypto assets.

We explore the reality of AI in compliance - moving away from the idea of AI as an "expert" to focus on how technology can realistically strip the administrative burden out of daily life. Heather also pulls back the curtain on FCA authorization, explaining why some firms fail and how a "live" Business Wide Risk Assessment (BWRA) is the secret to regulatory success.

Whether you’re a Fintech founder navigating your first EMI application or a compliance professional looking to step up into an MLRO role, this episode is packed with actionable insights on leadership, innovation, and the upcoming regulatory roadmap.

Key Topics Covered:

The AI Misconception: Why technology should replace admin, not human intelligence.

FCA Focus Areas: Mastering the methodology of Business Wide Risk Assessments.

EMI Application Strategies: Success tips for navigating the iterative authorization process.

The Future of Money: The role of stablecoins in cross-border payments.

Career Evolution: The personality traits needed to move from banking into compliance consulting.

Episode Timestamps

00:00 – Intro: Meet Heather O'Gorman, Head of Digital Assets at FSCOM

01:25 – Restructuring compliance teams for the UK market

02:27 – AI in Compliance: Replacing admin vs. replacing experts

03:55 – The "Live" Document: Mastering Business Wide Risk Assessments (BWRA)

05:48 – FCA Guidance: Best practices for methodology and control

06:30 – EMI Applications: Why success rates are picking up

07:48 – Finding the right expertise for the MLRO role

08:43 – "Act like a regulated firm before you are one"

09:30 – Why interim MLROs are difficult to approve

10:15 – Building a transparent relationship with the FCA

10:55 – Top 3 tips for a successful EMI application

12:55 – The MLRO as a business enabler, not a "police officer"

13:42 – Innovation and managing up: Advice for future MLROs

14:59 – Banking vs. Consulting: Does your personality fit the pace?

17:43 – 2026 Horizon: Safeguarding and the new Crypto Asset Regime

18:32 – Stablecoins and the future of cross-border payments

20:20 – The UK's regulatory roadmap for crypto firms

21:30 – Quickfire Round: Morning routines, Adam Lambert, and career "what ifs"

In this episode of Voices in Compliance, host Jason Thomas sits down with Willem Wellinghoff, Chief Compliance Officer at eCommPay, to discuss the evolving intersection of innovation and regulation. With over two decades of experience in the industry, Willem offers a unique perspective on shifting the compliance narrative from a "business blocker" to a strategic "revenue protector".

The conversation dives into the sophisticated reality of modern financial crime, the "pendulum swing" of UK and EU regulatory burdens, and the critical importance of a "curious mindset" when building future-ready compliance teams. Whether discussing the nuances of EMI applications or the tactical use of AI in onboarding, Willem provides actionable insights for founders and compliance leaders navigating the high-stakes global payments landscape.

Episode Timestamps

[00:00:47] Growth and Global Operations: Willem discusses eCommPay’s current growth phase and their strategic presence in London, Cyprus, and Riga.

[00:01:44] The Sophistication of Modern Crime: Insights into the dynamic nature of borderless financial crime and why teams need a "curious mindset" to stay ahead.

[00:03:25] The "Liveness" Trap: A tactical look at how criminals spoof onboarding security and the simple tests that can stop them.

[00:04:38] AI and the Human Element: Why technology is an efficiency enabler rather than a replacement for human oversight in compliance.

[00:06:15] Regulatory Intelligence: How the FCA’s approach has evolved from generic guidance to detailed "good vs. bad" thematic reviews.

[00:08:41] The EMI Application Conundrum: Why license pass rates are low and how the regulatory "pendulum" has swung toward higher burdens for founders.

[00:11:55] Pro-Level AI Prompting: Willem shares his personal process for using AI models to build better compliance frameworks.

[00:14:09] The Recruitment Dilemma: Advice on when to hire a senior MLRO versus utilizing fractional support during the licensing journey.

[00:17:40] Building a "Marriage" with the Regulator: The importance of openness, transparency, and coming to the regulator with solutions rather than just problems.

[00:22:14] Revenue Protection vs. Business Prevention: Rebranding the role of the MLRO as a strategic business enabler.

[00:25:45] The UK Tenure Trend: Analyzing why the average UK MLRO stays for only three years compared to longer tenures in other jurisdictions.

[00:34:50] The Evolution of Crypto and Stablecoins: Why the industry is shifting toward B2B payments and instant cross-border settlements.

[00:40:07] Staying Current After Two Decades: How Willem maintains his passion for the industry through news, AI queries, and community collaboration.

[00:43:23] Beyond the Boardroom: Willem shares his background in music and basketball, and his favorite Stanley Kubrick films.