Carter Hopkins
Sales
Interview Tips
Recruiting
Some searches are hard because the role is complex.
Some are hard because the talent pool is small.
Some are hard because the role hasn’t existed before.
We recently placed someone in a Director of Growth role. And while this was a unique search, the challenges and takeaways are the same ones we see across most high-level hires.
When the role is tied directly to revenue, time matters. Every week this seat stays open is a week of missed pipeline, delayed deals, and lost momentum.
Hiring a Director of Growth sounds straightforward.
The catch: in their 23 years of business, they had never had a salesperson.
This was a unique brief. Find a hunter willing to jump to a market they haven't officially pursued, for a firm with no sales infrastructure, no pipeline, and no playbook. The person placed would be building everything from scratch.
And like most companies hiring for a role like this, they didn’t just want the right person. They wanted them fast.
This client is a Dallas-based healthcare advisory firm that has spent over two decades helping some of the most senior leaders in American healthcare become better at what they do. Their advisors are former hospital CEOs, COOs, and C-suite operators.
Until this point, every client relationship they built came through word of mouth or a referral. Referrals have served them well. But with a new CEO, a fiduciary board, and a team of former hospital system executives behind them, the decision was made to grow.
They came to Pursuit with a clear need and a nuanced profile: find someone who could go out and build a book of business from scratch, selling complex transformation advisory services to healthcare CEOs and CFOs.
Their target deals are in the $500K–$1M+ range. The sales cycle is long. The product isn't software, it's a deeply human, relationship-driven service.
The role wasn't hard to fill; it was hard to define. They knew what they needed to accomplish, they just hadn't hired for it before.
That's where most searches start to slow down. When the role isn't clearly defined, time gets lost in alignment instead of progress.
One of the original requirements: "must have sold to medical groups." As we dug in, it became clear that wasn't actually the point. What they actually needed was someone who could sell high-ticket, intangible advisory services to C-suite healthcare leaders. Medical group experience was a bonus, but it wasn't the job. We reframed it as a strong preference and moved forward with a sharper brief.
That one pivot changed the search. Clarity on what actually matters is one of the biggest drivers of hiring speed.
For high-impact roles like this, we’re not pulling from active applicants. We’re starting from scratch, reaching out to candidates who aren’t looking.
The resume requirements were clear enough:
But the harder part was the intangibles. This person was walking into a 23-year-old firm with a deep culture, a strong identity, and no sales DNA. They had to be:
The last one mattered more than most clients think. This is a mission-driven company. They turn down clients who don't align with their values. The work they do (developing healthcare leaders) has a real downstream effect on patient outcomes. It's not just marketing copy; their advisors mean it. And the person selling that had to mean it, too.
Candidates submitted: 8
Candidates interviewed: 5
Total interviews: 13
Days, start to close: 62
The candidate we placed had been in healthcare sales for 16 years. Most recently, a VP of Sales at a healthcare insights company, selling to CEOs and CFOs on 9 -12 month cycles. Before that, she spent years at a major research and advisory firm, where she sold into C-suite technology and IT leaders with a 70/30 hunting-to-farming split.
The profile that stood out: she had sold complex, strategic, long-cycle services to senior executives in regulated industries. She knew how to prospect, build relationships with people who don't need you yet, and close deals that take a year to develop.
But what actually won the role was what she did after the interview.
She sent a 6-page strategic proposal. Unprompted. Outlining exactly how she'd approach the job. In fast-moving searches, signals like this matter. They create conviction and speed up decisions.
She was both a farmer and a hunter. And she proved the hunter part before she even had the offer.
1. Dialing in the job profile matters
The pivot away from "must sell to medical groups" wasn't a compromise. It was a clarification. The job description changes who you’re going after. There are “need to have’s,” and there are “nice to have’s,” and knowing the difference changes the search.
2. Greenfield roles require a specific kind of person
Experience isn't enough. Someone who thrives in a structured sales org with a warm pipeline and a built-out brand is a different hire than someone who can build from zero. Vetting for that distinction matters.
3. How a candidate shows up after the interview tells you everything
A 6-page proposal sent on their own initiative isn't a tactic. It tells you how this person will show up when nobody is watching; a character signal. Which is exactly what a first-of-its-kind role demands.
Most hiring delays don’t come from a lack of great candidates. They come from a lack of clarity on what you’re actually looking for.
