The VP or Head of Customer Success at a high-growth SaaS company is managing a revenue function. They own gross revenue retention, net revenue retention, and expansion ARR from the existing customer base. In many businesses, the expansion revenue owned by CS rivals or exceeds the new business number. This is not a support function. It is a commercial function with a different motion: relationship-led rather than acquisition-led, but no less commercially demanding.
The modern CS leader also manages an increasingly data-driven operation. They are expected to build and interpret health score frameworks, identify at-risk accounts before they churn, build playbooks for expansion conversations, and report on the commercial performance of the CS function with the same rigour as a sales leader. The days of Customer Success operating on instinct and relationship are not over, but the best leaders combine that instinct with data-driven operational discipline.
The Timing Question
The most common mistake SaaS scale-ups make when hiring a Head of Sales is moving too early. A sales leader hired before the product has found its market, before the sales process has been proven, and before there is enough deal history to understand what a good customer looks like is being set up to fail. They are being asked to lead a function that does not yet know what it is. The best Head of Sales candidates in the market understand this intuitively, which is why the most capable people often decline roles at companies that are not yet ready for them.
The signal that a company is ready for a Head of Sales is usually a combination of consistent deal closure from at least two non-founder salespeople, a repeatable sales process that can be documented, and a clear ICP that the team is executing against. Once these conditions exist, a Head of Sales can do what they are best at: build the team and process that replicates and scales the proven motion.
Builder vs Manager: The Critical Distinction
Not all sales leaders are the same. The most important distinction at the Head of Sales level is between people who thrive building from the foundations up and people who thrive optimising a system that is already working. These are different profiles and they require different things from a company.
A builder needs autonomy, tolerance for ambiguity, and the willingness to do things themselves before they hire people to do them. They need to be comfortable without a playbook, because their job is to write one. They need to be resilient when the first version of the process does not work and they have to iterate quickly. This profile is rare and commands a premium because the demand for it consistently outstrips the supply.
A manager needs structure, a clear brief, and the operational infrastructure to support a team. They thrive when the playbook exists and their job is to hold people accountable to it. This profile is more common and more expensive when placed in the wrong environment: a strong manager who has spent their career operating in mature sales organisations will struggle in a 15-person SaaS company without systems, processes, or certainty.
What the Brief Needs to Specify
A vague brief produces a vague search. If the role description says ‘build and lead a high-performing sales team,’ it tells a search partner almost nothing useful. It needs to specify: what does the team look like today, and what should it look like in 18 months? What markets are they covering? What ACV are they selling? What is the current sales cycle length and deal complexity? What has worked, and what has not?
The more specific the brief, the more precisely the search can be targeted. A Head of Sales who has spent ten years selling complex enterprise software at long sales cycles is a different person from a Head of Sales who has built a high-velocity mid-market function at sub-$50k ACV. Both are experienced sales leaders. Neither is right for both environments. The brief needs to specify which environment this is.
Assessing Leadership Credibility
The hardest thing to assess in a Head of Sales candidate is whether their success was genuinely theirs or largely structural. Someone who has delivered strong numbers at a well-known brand with an established product, strong marketing support, and a large SDR function has had significant structural advantages. Someone who has built and consistently delivered at a less well-known company without those advantages has demonstrated something harder and rarer. The numbers on a CV do not distinguish between these two profiles. A rigorous assessment process does.
Strong Search probes this distinction in every sales leadership search. We look at the conditions under which results were achieved, not just the results themselves. We speak to people who worked alongside the candidate, not just the references they provide. We test the depth of the candidate’s thinking about sales strategy, process, and people development in conversations that go well beyond the standard interview format.
If you are at the point where a Head of Sales hire is the right next step for your SaaS business, Strong Search can help you define the brief, identify the right profile, and find the person who fits it. Book a call with the team.
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