The Rep Report (August 2025)

Curated by ClosedWon Talent. Straightforward, practical hiring advice from recruiters who help Sales & GTM pros land better roles and succeed.

Author

Jay Green
August 28, 2025

📢 Welcome to The Rep Report!

You’re here because you want to make smarter moves, not just jump when things go sideways. In each issue, we’ll share practical advice, featured roles, and real-world guidance from recruiters who help Sales & GTM pros get hired at startups every day. Let’s get into it.

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🌟 ClosedWon Updates

Our blog is now LIVE and we’ll be adding more content over the next week (and ongoing). Check it out here.

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💡 The “Won” Thing You Should Know

One tactical tip each month to help you stand out and get hired…straight from the front lines.

If you’re interviewing for a new business AE role at an early-stage startup, you need one sharp story that proves you can create pipeline and close deals without a brand name or big machine behind you. Think of it like pitching a founder story (clear, scrappy, and specific.)

Here’s how to build it:

  • Set the scene: Don’t just say you had a quota. Show you defined the battlefield. “We were selling into cybersecurity, but the ICP wasn’t nailed down. I analyzed our first ten logos, spotted a pattern in mid-market fintech, and built a 50-account target list with CISOs and Heads of IT as decision makers.”

  • Show how you hunted: “I built my own outbound sequences, tailored to pain points in compliance audits, and landed a meeting with a top-tier CISO in three weeks.”

  • Explain your process: Walk through the steps you took without enablement or big-company resources i.e. how you qualified, navigated the cycle, and built trust.

  • Handle the unproven product: “Our product was missing a key integration, so I worked directly with their CTO and pulled in my founder to validate the roadmap to ease their concenrs.”

  • Close with results: “Closed a $300K ARR deal (the largest in company history) and my founder was so impressed he asked me to deliver my playbook to the rest of the team.”

  • Show adaptability: Wrap up with humility and forward-looking intent. “Every company is different. If I join your team, my first step would be to evaluate your current motion, see what’s working, and look for ways to add value fast.”

Early-stage founders and hiring managers aren’t just looking for closers. They want reps who can define ICP, create motion, and adapt their approach to fit a new market. Your deal story is how you prove you’re that rep who can thrive in ambiguity and without a lot of internal support.

Do you need help crafting your story? Feel free to ask a question here and we’ll respond with an answer.

Each month, we highlight a few roles we’re actively hiring for like AE, SDR, CSM, and more. If one looks like a fit for you (or someone you trust), let us know. We offer referral bonuses for successful placements.

Interested in one of these roles? Or have a friend to refer? Go here!

📢 Rep Shoutouts

Each month, we’re highlighting sales & GTM pros who have earned a promotion, joined a new company, or achieved other significant milestones:

🙋Ask ClosedWon

Real questions from real reps…answered by the team at ClosedWon Talent.

Question:

❝

I’m at a startup that’s a mess…very tough ICP, no product-market fit, and I just don’t have the support I need to be successful. My numbers look terrible. How can I pitch myself to another startup and stand out against reps who are crushing quota where they are?

Answer:

A: You don’t hide from it…you own it. Smart founders know not every miss is a rep problem. The key is to reframe your experience around what you learned and how you operated in the chaos.

Here’s how:

Show clarity, not excuses. Say, “Our product lacked core integrations and our ICP was still being tested. That environment taught me how to build outbound motions from scratch and pressure-test positioning with real buyers.”

Highlight transferable skills. Even if revenue didn’t land, stress the overlap with their market: “I’ve been selling into CISOs and security teams for two years. I know how they evaluate, what slows deals down, and how to build urgency.” That’s gold if their ICP matches yours.

Differentiate on adaptability. Make the point that you’ve lived through early-stage pain, and now you know what good looks like. That’s an edge over someone who only succeeded with a polished playbook.

Show your edge. This is where the chip on your shoulder becomes a strength. “I’ve been grinding in a tough situation. I’m hungry to prove myself, and if I get the chance here, I’ll bring that energy every day to blow out my number.”

Close with forward intent. “I’m looking to take those lessons and that fire into a team where I can apply them to a more defined motion and add value fast.”

Founders don’t just want clean resumes…they want killers who’ve been through tough markets, sold into their ICP, and come out hungry. That chip on your shoulder might be your biggest asset.

-Jay Green

Have a question you want answered? Ask away here.

📖Highlighted Guides and Resources

Want even more? Check out our website for additional articles here and check out our latest IG videos for tactical tips, interview prep, hiring insights, and more 👇 

🖋️ Stay in Touch

That’s it for this edition of The Rep Report. Feel free to reply with any questions or feedback. Thanks and see you next month!

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