The Rep Report (September 2025)

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

Author

Jay Green
September 30, 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

We just surpassed 6,000 followers on our ClosedWon Talent LinkedIn page! Thanks to everyone for following along on our journey, we are eternally grateful for all the support.

To repay favor, we want to double down to deliver even more valuable to the salespeople in our community, and to do that, we need your help!

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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.

Stop Letting OTE Blind You

I’ve watched a lot of good reps get seduced by the big salary + OTE package. It’s understandable. You see $150K base and a $300K OTE, and it feels like winning the lottery. But if the business fundamentals underneath that number are weak, you’re setting yourself up for a career stall…not a breakout.

Here’s the hard truth: OTE is a fake number. It’s built on assumptions about win rates, ramp speed, pipeline quality, and market pull. If the product isn’t selling, the territory is oversliced, or leadership doesn’t know what they’re doing, you’ll never see that OTE in real life.

Short-Term Cash vs Long-Term Value

Take thes two companies as an example:

  • Company A is offering $100–120K base. The product is hot, they’ve nailed their ICP, there’s real pull from the market, and the sales team is small but sharp. You’ll own a big territory, build real pipeline, and you’ve got a clear shot at blowing past your number.

  • Company B is offering $140–150K base. But dig deeper. Growth has stalled, churn is high, they’re stretching OTE targets to look competitive, and the team is bloated. You might make decent money in year one if you get lucky, but odds are you’ll be underwater and frustrated fast.

The smart reps pick Company A every time. Not because they don’t care about money, but because they understand how careers compound. Blowing out your number at a strong startup over 3–4 years builds a story that elevates your market value. You become the rep who helped scale a rocket ship. That’s leverage for the rest of your career.

Choosing Wisely Protects Your Market Value

If you take the high-salary, shaky-startup job and miss your number, it doesn’t matter that “everyone was missing.” The market doesn’t care. Your resume will show missed targets and short stints. That tanks your value.

If you take the lower-salary, strong-startup job and crush it, you’ll have the numbers, the story, and the references that hiring managers drool over. That’s how you turn a $120K base into a $400K+ earning trajectory over time.

Bottom Line

Top reps don’t chase the biggest number on paper. They chase environments where they can win. Because winning compounds. And nothing boosts your long-term value like a string of years where you overperform at a company that actually grows. The salary is just the surface. The conditions underneath determine your trajectory.

Do you need help choosing between a few offers? Or unsure if a company is worth your time? Feel free to ask a question here and we’ll respond with our perspective.

📢 Rep Shoutouts

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

And there was more movement this month than we’ve seen in a long time, so much so that it was tough to choose who to highlight. Here we go:

Want to be highlighted next month? Or know someone who might? Reply to this email or DM Jay Green!

🙋Ask ClosedWon

Real questions from real reps…answered by the team at ClosedWon Talent. This week, Jake Citrano is jumping in to answer three questions he gets asked by salespeople on a regular basis.

Question 1:

Question:

I received an offer from a company I’m very excited about and plan to accept. That said, I’m a salesperson and would still like to negotiate, especially since the offer is a bit under market and lower than a few other opportunities I was considering. What’s the best way to negotiate if I know I’ll accept either way?

Answer:

If you’re planning to accept regardless, you’ll want to negotiate with a light touch. For example, if the offer is $160k OTE, you could say:

"I’m thrilled to receive this offer - this is my top choice and I feel strongly I’m going to accept. That said, I’m also close to receiving offers in the $180k–$200k OTE range. If you were able to get me closer to the bottom of that range, it would make this decision even easier for me."

This approach communicates enthusiasm and commitment, while also giving the company a chance to improve the offer without creating tension.

Question 2:

Question:

I’m a strong mid-market salesperson looking to move into enterprise sales, but I’m having trouble since I’ve never sold directly into enterprise before, though I do have experience closing six-figure deals and working with large mid-market companies. What would you suggest I do?

Answer:

Often, the best way to move upmarket is through an internal promotion. If your current company doesn’t have that path, that’s okay - you can still position yourself well. Since you’re already a top candidate in the mid-market space, you have the luxury of being selective. Look for companies with a clear track record of promoting mid-market reps into enterprise roles. That way, you can advance while also increasing your compensation.

Another option is joining a startup where your focus begins in mid-market, but where you’ll also have opportunities to close enterprise deals. It’s a riskier path, but it allows you to prove yourself directly.

Question 3:

Question:

Should my resume be one page? I’m struggling to fit everything in.

Answer:

The “one-page resume” rule is largely a myth. The real key is clarity: make sure your resume includes the right level of detail in a clean, easy-to-follow format - without unnecessary filler that belongs in an interview, not on paper.

If that means your resume extends to two pages, that’s completely fine. Just know that the second page may get less attention, so make sure the most important information sits on page one. If something at the bottom feels critical to highlight, consider tightening elsewhere to bring it up front.

Have a question you want answered? Ask away here.

⭐Company Spotlight: Captura.io

A few weeks ago, I partnered with Captura on three critical roles (VP Sales, Advocacy & Community Manager, and Director of B2C Marketing.

Their business is fascinating -- they’ve built a vertical software solution for high-volume school photography studios. Their platform handles everything from uploading and editing photos to building custom packages and driving parent commerce. They dominate their niche with clear product-market fit, strong leadership, and serious growth plans.

Top sales leaders are actively choosing to interview there over other strong companies. The appeal is obvious to me: they’re profitable, well-run, and ready to hand the reins to a capable sales leader to scale.

This experience served as a reminder as to why I LOVE vertical software busineses (I’ve worked at two in my career). Here’s the top 4 reasons why I recommend them to a lot of sales reps:

  • Product Market fit is usually tighter because they solve deep, messy problems for a specific industry

  • Vertical software companies own a category…not a feature. Horizontal software often fight feature wars. Vertical software own the full operational stack for a niche

  • Referrals and reputation compound fast. Vertical markets are tight-knit. One strong win creates ripple effects across the entire industry.

  • Economic resilience. Vertical software often embeds itself into critical workflows which makes it harder to rip out during downturns.

If you haven’t experienced a business like this, take a look at Captura!

Once they hire their VP of Sales, I imagine they might be looking to hire some strong salespeople ;)

📖Latest Instagram Video

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!

Jay Green, Founder & CEO

ClosedWon Talent [Website] | [LinkedIn] [instagram]