Veteran CRO Carlos Delatorre prioritizes opportunities with complex products requiring a sophisticated sales motion. This environment allows him to leverage his expertise in building teams that can translate technical features into business value, create demand, and navigate internal customer politics, thereby making the market bigger.

Sales reps at market leaders often succeed due to brand strength and inbound leads, not individual skill. Instead, recruit talent who proved they could win at the #3 company in a tough market. They possess the grit and creativity needed for an early-stage startup without a playbook.

Instead of focusing solely on a candidate's current skills, Figma's CEO looks for their 'slope,' or their trajectory of rapid learning and improvement. This is assessed by analyzing their history of decision-making and growth mindset, betting on their future potential rather than just their present abilities.

OpenGov's CEO advises against the conventional wisdom of hiring salespeople with deep government experience. Instead, his company seeks hungry, courageous, and disciplined individuals and trains them internally on domain specifics, finding this approach more effective.

At the $1-10M ARR stage, avoid junior reps or VPs from large companies. The ideal first hire can "cosplay a founder"—they sell the vision, craft creative deals, and build trust without a playbook. Consider former founders or deep product experts, even with no formal sales experience.

When hiring for the C-suite, the importance of domain expertise varies by role. For Chief Product Officers, a deep passion and knowledge of the problem space is critical for setting vision. For engineering leaders (CTOs/VPs), specific domain experience is less important than relevant tech stack knowledge and transformation skills.

The long-term cost of a bad hire—in time, morale, and opportunity—far outweighs the short-term pain of a missed headcount target. Figma's CRO would rather leave a seat open for months than fill it with a candidate he's not truly excited about, even a "solid B player."

Peets argues the most crucial, untrainable skill for a startup sales rep is the demonstrated ability to generate pipeline and close net new accounts. He dismisses the common founder obsession with hiring from competitors, stating domain knowledge can be taught, but the grit to land new business cannot.

A sales leader's success at a company with a hot product that sells itself is a weak signal. Ben Horowitz prefers leaders from companies with complex, unsexy products (like PTC in the '90s). Their success proves a mastery of sales discipline, process, and playbook creation that translates anywhere.