This is a brutally honest look at the real downsides of tech sales, explaining why it's high risk, high reward, and not the right fit for everyone.
You’ve seen the $300K earnings posts. You’ve heard about reps crushing quota. But what about the flip side?
In this post, we’re going to break down the real downsides of a tech sales career. Not to scare you off—but to give you the honest perspective most people don’t share. If you’re serious about making it in sales, especially in tech, you need to know what you’re signing up for.
Every other YouTube video talks about $400K W2s and Presidents Club trips. And yes, those are real. But they’re only half the story.
Most people only hear the wins. They don’t hear about the dry spells, the layoffs, or the deals that die after 10 months of work. As Eric puts it, “You're fundamentally paid to lose more than you win.” That’s the part that separates the real pros from the wannabes.
Sales is the only career where losing constantly is part of the job description.
Expect to make 100 calls to set 2–3 meetings. Expect to lose 5–10 deals for every one you close. That’s normal. You’ll ride massive highs—like clearing $65K in one month—and then hit a dry spell for 4 months after your pipeline empties.
If you’re coming from school or a career where you got consistent praise and A+ feedback, this will mess with your head. No one gives you gold stars for effort. You only get paid when the deal lands.
Sales doesn’t reward perfection. It rewards outcomes.
You can run the perfect sequence, have a flawless call, and still lose the deal because someone got laid off or the company froze spend. One story from the video: Eric worked a deal for nearly a year only to watch the CEO cancel all software buys after layoffs.
That’s why elite reps always build more pipeline than they need. You need backup plans for your backup plans. Because sales leadership doesn’t care how hard you worked—only what closed.
You’re trading short-term risk for long-term upside.
If you haven’t performed and your company has a bad quarter, you're at risk.
Eric delayed moving into sales for 3 years because of this fear. But in hindsight, he says if you commit hard for 5 years, you’ll be more financially stable than 95% of other careers. The problem? Most people quit before they get there.
Sales pays well—but it doesn’t necessarily stack the same way engineering does.
If you’re an engineer, you can build a product and eventually go start your own company. In sales, you can make $400K but you can’t automatically build something from scratch unless you pick up extra skills like product or marketing on the side.
So if you want to eventually launch a startup, treat sales as an accelerator for exposure—but not the end game. Add skills while you earn.
Talent is third. Territory and timing come first.
If you’re selling to tech and you get assigned San Francisco, you’ll outperform someone with the same skill set in rural Iowa. If you’re at a market-leading product during hypergrowth, your deals will close faster and easier.
Top reps know how to align themselves with winners. It’s not just about being the best closer—it’s about being at the best place at the right time.
The title “salesperson” carries baggage. Be ready for it.
Eric is a former national team athlete, a Dean’s List scholar, and now a coach for Team USA. But when he shows up as an AE, it's not uncommon to be treated like he’s dumb by engineers and execs.
If you can’t handle being disrespected, this career will break you. If you can learn to keep composure, build trust, and prove yourself anyway—you’ll thrive.
Sales blends into life. Especially at the top.
Big deal on the line? Doesn’t matter if it’s date night or 1AM—you pick up the phone. If a VP needs an answer at 5AM, you're replying as soon as you see it. That’s the nature of high-level sales.
Eric isn’t saying you should grind 24/7. But if you want the upside, you’ll need to embrace the pressure and know when it’s worth it to pick up that call.
Q: Is tech sales worth it despite the downsides?
A: Yes—if you can handle volatility, rejection, and pressure, it offers unmatched financial and career upside compared to most W2 jobs.
Q: Do I need to be “naturally gifted” to succeed in sales?
A: No. Most top reps succeed by learning to manage pipeline, stay consistent, and navigate uncertainty. Talent matters less than resilience and execution.
Q: Can I start a business after 5 years in sales?
A: Not by default. Sales gives you exposure, but you’ll need to learn product, marketing, or operations to actually launch something.
Q: What if I’m afraid of being laid off?
A: That fear never fully goes away. But top performers with a strong network and results always land back on their feet—often at better companies.
Q: Is territory more important than talent?
A: At the highest levels, yes. Territory and timing impact your ability to succeed even more than raw skill. Choose your company and patch wisely.
→ If you’re serious about mastering tech sales and building a long-term career with real upside, check out Tech Sales Ascension. It’s the world’s #1 program for breaking in and leveling up—built for reps who want real results.
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