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Run Roleplays with Account Executive Candidates That Reveal Startup-Ready Talent

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Why This Format Works

Most early-stage startups don’t have polished decks, detailed personas, or long onboarding. You need sellers who can navigate ambiguity, bring energy, and stay coachable…not just memorize a pitch. That’s exactly what this roleplay helps you assess.


Use what they already know (their current product) to surface what you want to know:


  • How they run a sales conversation

  • How they react to feedback

  • How they think on their feet


The Roleplay Setup


Instructions (sent a day or two in advance):

“We’ll do a short roleplay in the interview. You’ll be selling the product you currently sell (or most recently sold), and I’ll play a target buyer. Treat it like a first call with no deck, no slides. Just a conversation. Ahead of the conversation, please send me a few bullet points around your typical persona and the pain you solve.”


This works because:

  • You’ll learn far more from how they guide a call than from what they say about your product.

  • The prep work they send ahead of time shows how much they care about preparing you for a great call and how well they know their buyer and product.


What to Look For


Coachability (Top Signal for Early-Stage)

After 5–6 minutes, pause. Give light, constructive feedback. Then ask:

  • “Let’s run that again from the top. Show me how you’d change things.”


They should shift their flow, language, or questions. Bonus points if they ask clarifying questions first.


Passion & Presence

Founders notice energy fast. You want someone who makes buyers lean in.

  • Do they light up talking about what they sell?

  • Are they present and sharp, or checked out and robotic?

  • Would you stay on this call if you were the buyer?


You’re hiring signal, belief, and enthusiasm…not just polish.


Buyer-Centered Thinking

Great sellers focus on the buyer’s world, not feature dumps.

  • Do they ask smart, open-ended questions?

  • Can they frame value in a clear, relevant way?

  • Do they recap what they hear?


This shows up more clearly when they’re selling something they actually understand.


Ability to Adapt

When you push back or add complexity, do they:

  • Re-center the conversation?

  • Ask for more info before guessing?

  • Stay calm and conversational?


Adaptability > Perfection


Debrief Questions to Ask

Use these to dig into their thinking process:

  • “What was your main goal in that call?”

  • “What would you do differently if this were real?”

  • “What’s your usual call prep process?”

  • “When was the last time a deal went sideways — and why?”


Final Thought

The best hiring processes aren’t generic…they’re intentional. A great roleplay isn’t about seeing if someone can wow you with polish. It’s about surfacing the real traits that matter in your environment: adaptability, conviction, curiosity, and execution.


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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