Posted in May, 2025 

  

Hiring your first AE or VP of Sales is one of the most important—and riskiest—moves a Health IT startup can make. Get it right, and you unlock scalable growth, investor confidence, and a path to repeatable revenue. Get it wrong, and you burn cash, stall momentum, and risk poisoning the pipeline with bad process.
This white paper outlines why most first sales hires fail, what to look for instead, and how to lay the right foundation before building the team. 

The Most Common Mistakes Startups Make 

• Hiring a “big logo” VP of Sales before you have a working process 

Just because someone scaled revenue at a major player doesn’t mean they can build from zero. Large-company VPs often inherit structure; they don’t create it. Without a clear ICP, messaging framework, and sales motion, they’ll struggle to adapt—and so will your sales.

• Hiring a generalist AE without Health IT experience

Healthcare is not an industry you can “figure out as you go.” Reps without experience in provider sales often underestimate the stakeholder complexity, buying timeline, and regulatory concerns—and deals die quietly in limbo.

• Expecting your first rep to build the system and sell within 30 days
  

No matter how talented, your first hire can’t invent your GTM strategy, build your collateral, create your CRM flow, and hit quota—all in their first month. Without structure, they’re guessing. And when they guess wrong, the damage ripples through your pipeline and credibility. 

• Skipping onboarding and expecting results without process

If you haven’t documented your pitch, demo flow, buyer personas, or follow-up sequences, you’re setting them up to fail. Reps need more than motivation—they need playbooks, coaching, and accountability. 

Red Flags: Signs Your First Hire Will Struggle  

• They focus on leads instead of process: “Just give me a list.” 
• They can’t explain how healthcare buying differs from other verticals. 
• They ignore regulatory, compliance, or clinical context in discovery. 
• They sell features before confirming pain. 
• They don’t know how to move an IDN from pilot to enterprise rollout. 

What to Do Instead 

• Hire a player-coach with Health IT DNA

Look for someone who’s comfortable closing deals and building foundational structure. They don’t just sell—they help you build a repeatable system around what works. 

• Build a playbook before you build a team

You don’t need a perfect process—but you do need enough structure to onboard, coach, and inspect performance. Without it, your sales org becomes a revolving door. 

• Consider fractional leadership to reduce risk and increase readiness

Before committing to a full-time hire, bring in a fractional VP or CRO to design the system, vet the role, and get the first deals across the line. This lets you test what’s working—and what kind of full-time leader you truly need.  

How Elevate HIT Sales Helps Mitigate Hiring Risk  

• We define the right role and profile based on stage, ICP, and buying complexity

No generic job descriptions—just targeted profiles built to match your motion, not your wishlist. 

• We support or lead onboarding with coaching, process design, and frameworks

From MEDDPICC® to messaging guides, we give your first hire the tools they need to succeed fast. 

• We bridge the gap between founder selling and scalable sales systems

We help you transition from “hero selling” to team execution—so your growth doesn’t live or die with the founder. 

The Result 

Fewer hiring missteps. Faster productivity. And a sales team built for your buyer—not just your board. 

Ready to move from instinct to infrastructure? 

Let Elevate HIT Sales help you make your first sales hire the right one—by building the systems that support them from day one.