In a recent Fidelity portfolio webinar co-hosted with Erevena, two seasoned operators broke it down with refreshing honesty and insight:

• Matt Mills, former CRO at 10x Banking & CCO at Featurespace

• James Allgrove, former Head of Revenue & Growth at Stripe & CRO at Fidel API

They explored when to make the leap, what to look for in a commercial leader, how to avoid costly mis-hires, and what “good” really looks like, especially when you're in growth mode.

Whether you’re prepping for your first strategic hire or questioning if your current setup is working, this write-up shares the most valuable takeaways from that conversation.

Here’s the short answer: A VP of Sales drives deals; a CRO drives strategy.

While a VP of Sales typically manages a sales team and quota, a CRO owns the entire commercial engine, sales, marketing, and customer success, and ensures alignment with product and leadership strategy.

They’re a core member of the executive team in the boardroom, influencing go-to-market direction, and not just managing pipeline. If you're asking whether your CRO should have a quota, you're probably still looking for a great VP of Sales.

A common milestone is around the $10M ARR mark. Founder-led sales can start to hit limits, and the commercial side of the business becomes too complex to manage ad hoc. That’s when having someone to lead and align all go-to-market activity starts to add real value.

Timing matters here. Don't make knee-jerk hiring decisions based on a single bad quarter or macroeconomic pressures. Instead, assess what you are really hiring for and what you are wanting them to do.

• Are you solving a leadership bandwidth problem?

• Are you trying to reposition your entire GTM function?

• Or is the issue process? Product-market fit? Pipeline quality?

Getting this wrong may lead to mis-hires, with CROs and management having conflicting expectations. A CRO can't fix a 24-month sales cycle in six, so be clear on what issues you’re trying to solve for and set expectations accordingly.

James broke it down into three axes:

1. Sales leadership: Can they get in the weeds and close deals when needed?

2. Team leadership and coaching ability: Can they coach teams and lead culture?

3. Operational discipline: Can they dig into the numbers to understand pipeline and forecasting as well as shift strategic CTM dynamics?

The catch? Most people don’t spike in all three. So calibrate based on what your company needs. Are you doing enterprise? Is your marketing underpowered? Do you need better alignment with the product?

CROs are great at selling—especially themselves. Here's how to get signal, not noise:

• Check their prep: Can they explain your product, GTM motion, and customer profile from just your website?

• Conflict history: “Who do you usually clash with?” reveals how they work cross-functionally.

• Reference widely: Go beyond direct reports and managers—ask product, finance, and ops peers how the CRO worked cross-functionally.

Also, don’t rely too heavily on whether they hit quota. It’s important, but context matters. You want to understand how they think, not just what their number was.

Going stateside is a common tipping point. It’s also where the CRO role really earns its keep. A few principles came through strongly in the conversation:

• Start with a pod: sales, support, marketing, and ops.

• Seed with 1–2 internal transfers to maintain culture.

• Localise your approach. US buyers often value domestic case studies over international wins. You may need to offer your first few US clients favourable terms just to get a foot in the door.

• Ensure you still have senior presence. One week a month on a plane, building relationships—that still moves the needle.

A CRO isn’t just a title; if hired right, they are a transformational hire. They bring structure, alignment, and long-term thinking. But to succeed, they need clarity of mandate, cultural fit, and the space to build—not just to sell.

A big thanks again to Erevena and panellists James Allgrove and Matt Mills for their candid insights.