📢 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 helped eleven incredible people get hired in October, with 19 open roles that we’re actively working on. This was our best month ever in terms of volume of hires, and with a team of 3, we’re proud of what we accomplished! But…we have ambitions to help a lot more people than that on a monthly basis.

And we’re working on ways to make that possible…stay tuned!

🔑 Featured Post

Why 95% of AE’s Never Make It Into Elite Startups…and What You Can Do To Get There

Everyone wants in on the next breakout SaaS story. The kind of startup where top performers print money, build credibility, and open every career door that follows. But the truth is, most AEs never even get close.

It’s not because they lack skill or drive. It’s because they’re out of alignment with what those startups actually value and how they evaluate talent.

After working with more than 200 early and growth-stage SaaS companies, the patterns are clear. The same reasons come up again and again when hiring managers pass on candidates before a first call.

Why Most AEs Get Filtered Out

When founders and revenue leaders review your background, they’re not just asking whether you can sell. They’re trying to understand if you can sell in their environment.

These are the most common dealbreakers:

1. No SaaS experience – Selling products or services doesn’t translate directly to selling recurring revenue. Founders know the difference.

2. No clear track record of overperformance — strong AEs lead with proof: quota, attainment, and wins that show they consistently outperformed peers.

3. Too many short stints – Jumping every year (or every other year) makes it harder to showcase consistent high performance, especially when compared to other candidates who can show the performance plus internal growth and promotions.

4. No deal context – Hiring managers need to know what type of motion you’ve run: transactional, mid-market, enterprise, or strategic.

5. Irrelevant industries – Experience in unrelated markets doesn’t carry much weight for SaaS, especially in technical verticals.

6. Fluffy resumes – Long, vague descriptions with zero numbers show poor self-awareness and weak results.

7. No startup experience – If you’ve only sold with brand recognition and inbound pipeline, it’s hard to prove you can generate momentum from scratch.

8. Weak LinkedIn presence – Most AEs treat LinkedIn like a digital résumé and it shows. Generic headline, copy-paste job descriptions, no measurable results, and no sign of growth. Their profile reads flat…same title, same responsibilities, no movement. No internal promotions, no mention of Presidents Club or quota attainment, no story that connects their experience. They don’t seem like they have the “it” factor.

You can tighten your resume, quantify results, and tell better stories, but surface-level changes won’t erase the underlying experience gaps. Founders want people who’ve already sold through chaos and ambiguity…reps who can create motion without enablement, inbound, or brand recognition.

The good news is that you can build that background. It takes strategy and patience, not luck.

How to Make Yourself Competitive

Top performers don’t wait for elite startups to take a chance on them. They reposition their career to make it an easy yes.

Here’s how they do it:

1. Take a Step Back to Build True SaaS Experience

If your experience is in tangible goods or services, you’re asking hiring managers to take a massive risk by putting you in a mid-market or enterprise SaaS role. They won’t.

A smarter move is to take a step back, whether that means an SDR role, SMB AE position, or hybrid sales role to learn how SaaS actually works. You’ll build the foundational skills that matter: running discovery, managing renewals, tracking usage metrics, and selling on value instead of product specs.

It might mean a smaller paycheck upfront, but it’s a fast path to credibility. One year of proven SaaS results is worth more than three years of experience that doesn’t translate.

2. Leverage Industry Expertise To Bridge Into SaaS

If you already know a specific vertical, that’s leverage…use it!

A rep who’s sold to hospitals, manufacturers, or logistics teams understands how those buyers think, how they evaluate tools, and what slows down deals. That knowledge is gold to a SaaS startup trying to win that market.

Instead of trying to reinvent yourself, target startups that sell into the space you already know.

If you’ve been in medical sales, look at healthtech SaaS. If you’ve been in manufacturing, explore industrial or supply chain SaaS. You’ll speak the language of the customer and ramp faster than someone who doesn’t.

Translate your wins into terms that fit SaaS:

• “Managed multi-stakeholder sales cycles in hospitals across five states.”

• “Helped clients adopt technology that reduced manual workflows by 30%.”

That turns industry credibility into startup value.

3. Use Growth-Stage Companies as a Launchpad

If you want the chaos (and glory) that comes from being at a 10-person seed-stage startup, but don’t yet have the resume to back up that move, aim for a Series B–C company with solid product-market fit. These companies already have process and traction, but still need reps who can think like builders (and likely won’t be as particular about background and experience).

You’ll get structure, but not bureaucracy. Support, but not hand-holding. It’s the best way to learn the startup rhythm (pipeline creation, territory ownership, and fast iteration) without being thrown into total uncertainty.

After a couple of strong runs here, you’ll have what early-stage founders actually want: proof that you can win without a big brand behind you.

This is specifically credible if you launch or grow a new vertical or can show you operated in a “startup environment” within a larger organization.

What Separates the Top 5%

The AEs who make it into elite startups don’t just have better resumes. They make better career decisions. They choose environments that stretch them, not just pay them.

They’ll take a smaller base at a company with product-market fit, strong leadership, and clear upside, instead of chasing inflated OTEs at companies with no real traction. They understand that one great run (where they overperform and help scale something real) will multiply their market value for years.

Meanwhile, most reps keep chasing short-term compensation, miss their number, and end up explaining two-year stints for the next decade.

If you want a seat in an elite startup, build the track record that earns it. Choose roles that sharpen your skills, not just pad your title. In a few years, you won’t be fighting for interviews…founders will be fighting to hire you.

🙋Ask ClosedWon

Real questions from real reps…answered by the team at ClosedWon Talent. This week, we’re answering one question from someone in our network.

Question:

Answer:

You’re not the first good rep to get caught in a bad startup situation. It happens all the time. What matters now is how you frame it and what you learned from it.

Here’s how to handle it cleanly:

1. Own It Without Oversharing

Don’t bury the job, and don’t overexplain it. Keep it tight. Something like:

This signals maturity. You’re not blaming anyone, and you’re not making excuses. You’re showing awareness.

2. Shift the Focus to Your Decision-Making and Reflection

Hiring managers respect reps who can self-diagnose. Follow up with something like:

That tells them you’ve learned from the mistake…which actually builds credibility.

3. Re-Center on Your Track Record

Bring the conversation back to what’s consistent in your career:

That’s the close. You’re showing both performance and intent…two things early-stage founders care deeply about.

4. On Paper: Keep It Real, But Contained

On your resume, don’t hide the job, but also don’t overemphasize it.
Keep it simple:

AE – XYZ Startup (2024–Present)

• Hired to drive new business for a Series A company in a developing market

• Created outbound structure and contributed to early customer feedback loops

• Added xyz in new pipeline, 90% self-sourced with F500 prospects in our target list

That’s it. No need to list missed quotas or vanity fluff. Just factual and neutral that shows you did what you were supposed to do…catch the attention of dream customers!

Bottom Line:

One off-target move doesn’t define you. What kills people is trying to spin it or hide it. Be honest, show reflection, and shift the spotlight back to your long-term performance.

The best founders and hiring managers will respect that you’ve been through a rough patch…because they’ve lived the same thing themselves.

Have a question you want answered? Ask away here.

🖋️ 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]