Hiring your first head of sales is a make-or-break move. In this episode recap from Knocking to 10, Alex Grace shares hard-earned lessons on why most early sales hires fail — and what founders actually need at the Series A stage. From avoiding farmer reps to building sales processes that fit your reality (not your dreams), this is a blueprint for getting it right.
Alex Grace has done it all—boiler room sales floors, zero-to-one founder-led teams, post-Product-Market Fit scale-ups, and high-growth SaaS orgs. A four-time VP of Sales and current revenue leader at Arta, Alex has built and rebuilt GTM machines from the ground up.
In this episode of Knocking to 10, Alex joined us to unpack the gritty truths about hiring sales leaders, avoiding common founder pitfalls, and building scalable outbound motions that actually work.
Hiring a VP of Sales or CRO is one of the most common—and costly—mistakes founders make too early.
Key Lesson: Your first sales hire needs to be a hunter, not a strategist.
Key Takeaway for Founders: If you're still figuring out how to sell your product, you need a strong individual contributor who can extract the sales motion from the founder, close deals, and build the process—not someone who expects a fully built playbook on Day 1.
“Founders hire farmers when they need hunters—and then blame them when they can’t grow crops in an empty field.”
That all-star rep from your competitor might look great on paper. But if they’ve spent the last five years farming inbound leads, they’re unlikely to succeed in a scrappy startup environment.
Key Lesson: Startup sales success requires a different muscle than late-stage execution.
Key Takeaway: Ask candidates when they last prospected, sold without brand recognition, or built pipeline from scratch. The right hire for you today probably isn't the one your board thinks looks impressive.
Founders often expect results too fast—and fire too quickly.
Key Lesson: Building a repeatable sales motion takes longer than you think.
Key Takeaway: Onboard your new sales leader like your first rep. Expect 3–4 months to ramp, and a full year to evaluate effectiveness. Look for momentum signals: pipeline growth, improved conversion rates, shorter sales cycles—not just instant revenue.
“If it took you 18 months to get your first customers, why are you giving a new VP 3 months to work a miracle?”
When stepping into a new leadership role, it’s tempting to clean house. Don’t.
Key Lesson: Default to keeping reps, not replacing them.
Key Takeaway: Use a coachability framework. Are they showing up? Taking feedback? Improving? If not, move quickly—but own your side of the hiring and onboarding process.
“Replacing someone is often harder and riskier than developing them. Start by asking: have we set them up to succeed?”
One of the biggest mistakes Alex sees? Sales leaders showing up with a one-size-fits-all methodology from a past job.
Key Lesson: Fit the motion to your buyer and problem—not your past experience.
Key Takeaway: Start by understanding where your buyer is when they feel the pain. Listen to calls. Interview customers. Revisit losses. Then build your playbook from the ground up.
“If I owned a tire shop, I’d advertise in every pothole in the city.”
Alex’s current motion at Arta includes “salon dinners”—intimate, value-driven events for buyers to connect, share insights, and build trust (without being sold to).
Key Lesson: High-ACV sales still run on relationships.
Key Takeaway: Find where your buyers congregate when they’re feeling the pain. Show up there. Don’t pitch—create value and build credibility over time.
Alex didn’t hold back when it came to industry trends:
Key Lesson: Great sales leadership starts with people.
Key Takeaway: Don’t get lost in tools, dashboards, or process. Invest in your team. Be a resource. Assume good intent. And never forget that your job is to help people grow.
“You owe your team a duty of care. Either put in the work to help them succeed—or help them move on with honesty and respect.”
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