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.

Sales coaches excel at turning a functional, founder-led sales process into a scalable machine. They are not equipped to solve the fundamental problem of figuring out your initial case study and factory from scratch. Hiring one before you have a repeatable motion is premature and will likely fail.

Founders often believe they can hire one "integrator" (like a COO) to handle all operational details. This is a myth. True scaling requires hiring specific, talented functional leaders (e.g., Head of Sales, Head of Product) who can solve a single, major business constraint, not a generalist helper.

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.

Avoid hiring a growth leader with a big-name pedigree for your early team, as they are often unsuited for the necessary hands-on experimentation. Instead, seek young, hungry builders who are motivated by chaos and comfortable rebuilding their own work as the company's needs evolve.

A startup's initial salesperson should prioritize mirroring the founder's successful sales approach. Their job is to deconstruct the founder's "hook" through observation and trial-and-error, not to immediately implement formal sales processes, metrics, or a CRM. Success comes from successful knowledge transfer, not premature system building.

Founders often chase executives from successful scaled companies. However, these execs can fail because their experience makes them overly critical and resistant to the painful, hands-on work required at an early stage. The right hire is often someone a few layers down from the star executive.

Hiring someone with a prestigious background for a role your startup isn't ready for is a common mistake. These hires often need structure that doesn't exist, leading to their underutilization and boredom. It's like using a "jackhammer when all we needed was a sturdy hammer."

A sales leader's success is determined less by personal sales ability and more by their capacity to attract a core team of proven performers who trust them. Failing to ask a leadership candidate 'who are you going to bring?' is a major oversight that leads to slow ramps, high recruiting costs, and organizational inefficiency.