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The First 3 Sales Hires: Roles, Risks, and Red Flags

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Why This Matters

The first few hires carry outsize weight. They are not just closing deals. They are testing whether your motion works and creating the repeatable steps you will scale. Hire well and you accelerate revenue, clarity, and confidence. Hire poorly and you lose time, deals, and conviction in your GTM.


What Founders Often Get Wrong

  1. Hiring late stage closers as first reps

    1. Great closers from big orgs often rely on enablement, brand, and process. Early stage needs learning and self sufficiency.

    2. Flip it: Hire for discovery, adaptability, and the ability to self source pipeline.


  2. Cloning the first hire

    1. Two of the same profile leaves gaps in coverage. You need complementary strengths to pressure test the motion.F

    2. lip it: Make hire two intentionally different so you reinforce what is working and challenge what is not.


  3. Going too junior on the third hire

    1. Affordability is not fit. Hire three should signal the motion scales beyond your network and founding team.

    2. Flip it: Prioritize proven success with similar buyers and processes and fast onboarding with minimal hand holding.


What Great Early Hires Do

  • Own a motion and sell daily

  • Turn feedback into a tighter pitch and process

  • Create the first simple, repeatable steps

  • Prove momentum with clear proof points


The First Three Hires


1) Founding AE: The Learning Partner

  • What They Do: Sell, adapt, and help shape the sales process from the ground up.

  • What to Look For: Strong discovery, curiosity, early stage appetite or experience, familiarity with your buyer or adjacent markets, ability to self source and close.

  • Common Risk: Late stage closer who has never built pipeline or worked without enablement.

  • Red Flag: Obsession with deck polish and process over adaptability and learning.


2) Second Hire: The Complement

  • What They Do: Reinforce what is working and challenge what is not.

  • What to Look For: Different strengths than hire one, experience with similar industries or personas to shorten ramp, collaboration, and comfort asking hard questions about the pitch and motion.

  • Common Risk: Hiring a clone of the first AE and missing coverage in key areas.

  • Red Flag: "Just tell me what to say and I will say it" mindset.


3) Third Hire: The Signal

  • What They Do: Validate that the motion can scale beyond the founding team.

  • What to Look For: Came from outside your personal network, proven success in similar markets and processes, quick ramp with minimal hand holding, perspective from a similar stage or buyer journey.

  • Common Risk: Hiring too junior and mistaking affordability for fit.

  • Red Flag: You are still adjusting the role 30 days in because the earlier scopes were unclear.


Final Thought

Your first three sales hires set the tone for culture, motion, and momentum. Choose builders who sell. Scope each role to learn fast and prove repeatability. That is how you avoid regret and build a team that wins.


About ClosedWon Talent

ClosedWon Talent is a specialized sales recruiting firm that helps growth focused companies hire top GTM talent. We partner with founders, revenue leaders, and investors to build high performing sales teams across SaaS and beyond.


What sets us apart is the ClosedWon Method, a proven recruiting framework built on speed, precision, and transparency. We combine deep industry expertise with a curated candidate network to deliver shortlists of qualified, motivated sales professionals fast. Our team does not just fill roles, we act as embedded partners who understand how to assess selling style, territory experience, and growth potential based on each clients' specific needs.


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