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Hard Truths for New AEs: What Every Seller Needs to Know About Their Sales Career and Career Pathing

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Congratulations—you made the jump or you’re ready to level up in sales and move to a better situation. You’re officially going for it as an AE (Account Executive). Whether it’s your first closing role or your third attempt at making sales a long-term career, you’re about to get a crash course in what no one tells you in onboarding.

Sales can be incredibly rewarding—but also incredibly misleading. Here’s what I tell every new AE I coach or train through our sales training programs: the real lessons don’t come from enablement decks. They come from how you evaluate your path, protect your leverage, and control your own narrative.

Let’s dig into three truths that will help you build a repeatable, sustainable, and sane sales career—starting with your first (or current) AE role.

1. It Takes 2–3 Sales Roles to Know if Sales Is Right for You

Let’s be clear: sales is not one-size-fits-all.

The AE role at a 30-person SaaS startup is wildly different from the AE role at a Fortune 500 tech giant. Your manager, your quota, your support, your product-market fit—all of it impacts your experience and success.

If your first role feels like a trainwreck, that doesn’t mean you suck at sales. It might just mean you’re in the wrong environment. I’ve coached countless reps who failed at one company, only to thrive in a better-supported org that used a smarter sales process.

What This Means for You:

  • Don’t give up on sales after one bad job.
  • Give yourself permission to “sample the field.”
  • Track what works (and doesn’t) for you in each role. Is it culture? Leadership? Sales tech? Deal velocity? Get real, and get specific with yourself as you do this examination.

Sales is a craft. It takes time to find your fit and develop your rhythm. Our sales coaching helps reps develop long-term sales careers—not just survive their first 12 months.

2. You’re Always a Free Agent

One of the biggest sales career mistakes I see early AEs make? Getting too comfortable.

Even after you land a role, you are still a free agent. That’s not disloyal—it’s professional self-preservation. Sales is a volatile field. Quotas shift. Leadership changes. Budgets get cut. Good reps get let go for bad reasons.

“You’re not your company’s employee. You’re your own company’s asset.”

What This Means for You:

  • Always keep your LinkedIn current.
  • Keep networking, even when you’re happy.
  • Check in with recruiters quarterly.
  • Build a personal brand. (Your LinkedIn and Reddit content is your résumé.)

Need help staying competitive? Our SaaS Sales Training equips you with the real skills modern employers are hiring for—and that keep you relevant even in down markets.

3. Keep Interviewing 30–45 Days After You Start the Job

Yes, even after you’ve accepted an offer.

The reality? Most red flags in a sales org don’t show up until you’re a few weeks in. That’s when you find out the quota is unrealistic, the CRM is a mess, and your “warm leads” are actually ice cold.

That’s why I tell every rep: keep your interview funnel alive for the first 30–45 days. Treat your onboarding phase like an extended vetting process—for the company.

Warning Signs to Look For:

  • Sales enablement is disorganized or nonexistent.
  • Your comp plan is unclear or constantly changing.
  • Leadership doesn’t handle objections—internally or externally.
  • No clear sales playbook or prospecting process.
  • You’re already burned out by week 3.

4. Questions to Ask BEFORE You’re Hired

Want to spot moldy cheese before it stinks up your sales career? Ask these questions during the interview, and if you’re too afraid to do it then definitely ask in your first 30 days:

  • What % of reps hit quota last quarter?
  • What happens if I miss my number for the first few months?
  • Who’s the top-performing AE and what makes them successful here?
  • Is there a formal sales coaching process in place?
  • What does ongoing training look like after onboarding?

If leadership is vague or defensive, that’s your sign.

5. What Makes a Great Second or Third Sales Role?

If your first AE role is a “learning job,” your second and third roles should be “growth jobs.”

Here’s what to look for:

  • A strong coaching culture (not just product training).
  • Clearly defined territories and verticals.
  • A process for navigating multi-threaded sales and buying committees.
  • Visibility into pipeline and forecast expectations.
  • Mentorship from experienced sellers.

Not sure what to prioritize in your next role? Our guide on choosing a sales trainer outlines what top-performing teams look like—and how to spot them before you accept.

6. How to Keep Your Interview Pipeline Alive

Even when you’re “off the market,” it’s wise to keep the wheels turning:

  • Block 30 minutes monthly to apply for roles you’d actually take.
  • Take 1–2 “curiosity calls” each quarter from recruiters.
  • Use platforms like Bravado, RepVue, and Pavilion to assess companies.
  • Post 2x/month on LinkedIn with thoughts, learnings, or results.

This isn’t about job hopping. It’s about keeping your sales career momentum active. Like we teach in N.E.A.T. Selling™, the best reps are always qualifying—even for themselves.

Final Word: Don’t Just Survive Your First Sales Job—Design Your Career

If you’re an SDR making the leap, or a new AE figuring it out on the fly, remember:

  • Give yourself grace. Not every job defines your worth.
  • Stay curious. Keep learning, keep testing, keep networking.
  • Stay ready. Because in sales, agility beats loyalty every time.

Whether you’re looking for 1:1 support, team coaching, or a full sales enablement strategy, The Harris Consulting Group is here to guide you from “just hired” to “top performance.”

Ready to talk about your sales team or personal growth?

📞 Call or text Richard directly at 415.596.9149
📅 Or schedule a free consultation

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