Hiring and structuring commercial leadership roles is one of the toughest, and most critical, challenges fintech founders face during scale-up. To demystify the evolving role of revenue leaders, Erevena hosted a webinar in partnership with Fidelity, featuring expert insights from Matt Mills (former CRO at Featurespace, now advisor to tech companies) and James Allgrove (ex-Stripe and former CRO at Fidel API), moderated by Maria Josife, Partner at Erevena.
Here are the key takeaways from a rich discussion that spanned hiring strategy, performance management, US expansion, and the CRO vs VP of Sales debate.
What’s the Difference Between a CRO and a VP of Sales?
One of the most commonly asked questions during the webinar was: what’s the real difference between a CRO and a VP of Sales? According to Matt Mills, “If there’s a debate about whether or not your CRO needs a quota, you’re not hiring a CRO.” The distinction is fundamental. A VP of Sales is responsible for executing a predefined plan and leading the sales team. A CRO, by contrast, is a strategic partner to the CEO, shaping the commercial vision, market positioning, and overall go-to-market approach.
James Allgrove reinforced the difference by explaining that a CRO typically owns not only sales but also customer success and sometimes marketing. This executive-level role is about aligning commercial functions, influencing strategic decisions, and helping scale the business through each growth stage. Most companies reach a point, often around $10M in revenue, when this kind of leadership becomes critical.
When (and When Not) to Replace a CRO
Recent years have seen a wave of CRO transitions, particularly in companies that raised capital during the high-growth era of 2019–2021. However, Matt Mills warned against rash decisions: “There’s often a knee-jerk reaction to replace the CRO, but before making that call, ask: is this a product-market fit issue? A competitor problem? Or a service issue?”
The panel emphasised the importance of diagnosis. Replacing the CRO won’t fix underlying issues with product readiness, marketing alignment, or unrealistic board expectations. Companies must align performance expectations with realistic timelines, particularly in enterprise sales environments where cycles are long and complexity is high.
The Right CRO for Your Stage
A recurring theme was the importance of stage-appropriate hiring. Companies often make the mistake of hiring senior candidates from large corporations for the prestige or their Rolodex, only to discover they’re not the right cultural or operational fit.
Instead, founders should focus on candidates who are comfortable operating in ambiguity, thrive in fast-moving environments, and have experience scaling from similar stages. James Allgrove described three key axes when evaluating a CRO:
- Sales leadership and coaching ability
- Numerical fluency and forecasting
- Strategic thinking and go-to-market vision
The right CRO will spike in one or two of these areas based on the company’s customer type, motion (SMB vs enterprise), and existing team strengths.
Should Marketing Report to the CRO?
The short answer: usually, yes. In today’s B2B environment, marketing and sales are more closely connected than ever. Matt Mills argued that marketing should sit under the CRO unless there’s a compelling reason not to, especially when go-to-market efforts rely heavily on ABM or hybrid BDR strategies.
James Allgrove agreed, noting that separating the two functions can lead to misalignment, particularly when sales dismiss marketing leads as unqualified or irrelevant. However, he added nuance, if a company operates with both self-serve and sales-assisted motions, such as in SMB SaaS, it may make sense to separate demand generation from strategic marketing leadership.
Managing Expectations: Leading Indicators Matter
New CROs must establish expectations early and shift the focus from lagging indicators (like revenue) to leading ones (like pipeline health). “Introduce a micro-win strategy,” advised Matt Mills. “Track RFPs, SQLs, accepted proposals, every leading indicator.”
James Allgrove added that new CROs should immediately clear out stale pipeline and assess the team’s readiness. Only by resetting the forecast and being transparent with the board can they create the space needed to rebuild and grow sustainably. Both speakers emphasized that strong CROs communicate openly and measure progress in a way that reflects business complexity and maturity.
Expanding into the US: Start Small, Stay Close
US expansion was another hot topic. Both Matt and James advocated for a bottom-up approach over a top-heavy leadership hire. “Start with what you have in your home market and try to find product-market fit in the US, don’t reinvent from scratch,” said James Allgrove.
He recommended a “landing team” model: a pod of 3–5 cross-functional people who understand the product and culture. Importantly, at least one or two should come from HQ to preserve values and momentum. Matt Mills added, “Americans don’t care about international case studies. Your first US client is everything.”
Founders must stay involved, ideally visiting monthly or relocating temporarily, to replicate the early energy that drove domestic success. And they must resist over hiring or overspending on expensive execs who may not understand the product or team.
Favourite Interview Questions for CROs
To close, both speakers shared their favourite interview questions to assess CRO candidates:
James Allgrove: “Can you explain what our product does and who it’s for?” A deceptively simple question, but one that filters out underprepared candidates quickly.
Matt Mills: “Who historically do you fall out with?” This sheds light on the candidate’s ability to collaborate with peers across finance, product, and delivery, and whether they may create tension in high-stakes leadership teams.
Final Thoughts
As Maria Josife noted in closing, many early-stage companies over-index on titles too early. Instead of naming everyone a CRO, it’s more effective to layer your leadership team, bringing in a VP of Sales first, and layering in a CRO when true executive-level strategy is needed.
The key to hiring a successful CRO lies in diagnosing what your company truly needs: a quota-carrying deal-closer, or a strategic leader who will shape your entire commercial motion.
About the Authors:
Maria Josife
Partner, Erevena
Maria leads the European FinTech group at Erevena, with a focus on Consumer FinTech, InsurTech, Payments, Open Banking, Banking Technology, and Data and Fraud Detection. With over 20 years of executive search experience, she is also actively involved in the firm’s Board practice, specialising in CEO and Founder succession in both FinTech and Digital sectors. Recent clients include FinTech companies like Moneybox, Preqin, Payhawk, Moonfare, Monavate, and FastSpring, as well as CEO placements with companies such as Polarsteps, Huboo, Jodel, and CountingUP.
Matt Mills
Go-to-Market Advisor & Former CRO
Matt is an experienced commercial leader who most recently led the commercial function at Featurespace, a UK technology success story acquired by Visa. With a background that includes launching advanced tech propositions and scaling go-to-market operations globally, Matt now advises high-growth companies on commercial strategy, sales performance, and turnaround execution. He’s passionate about aligning commercial teams with company strategy and building scalable, efficient revenue organisations.
James Allgrove
Go-to-Market Advisor & Former CRO, Fidel API
James began his career at Bain & Company before moving into fintech and SaaS. He was Stripe’s first commercial hire in Europe, where he built out the UK and US teams, scaling the latter from 5 to over 200 people. Most recently, he served as CRO at Fidel API and now advises seed to Series B startups on go-to-market strategy, international expansion, and team design. James brings deep operational experience and a strategic mindset to help founders scale revenue in complex, evolving markets.
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