What 10 Years in Tech Sales Actually Feels Like (The Stuff No One Tells You)

INTRO

There’s a lot of hype online about tech sales—how fast you can make money, how to break in, how to hit quota. But what happens after that? What’s it really like to be in this career for 5… 10… 15 years?

In this conversation, Eric Finch sits down with Enterprise Account Executive Anthony Saucedo to talk about the side of tech sales no one covers. Not the clickbait stuff. The real human experience of building a long-term career in a high-pressure, high-reward industry.

If you're serious about staying in this game—and not just getting in—this one's for you.

WHAT YOU’LL LEARN

• How early success in sales can set you up for future struggles
  
• What it actually takes to survive (and grow) through layoffs, reorgs, and long enterprise cycles
  
• The mental and physical routines that help top reps stay sharp
  
• How to build mentorship and internal credibility that protects your job—even in down markets
  

CONTEXT: WHY THIS MATTERS

Most people don’t last long in sales—not because they’re not talented, but because they weren’t prepared for what happens after the honeymoon phase.

In Anthony's experience:

‍From 23 to 25, I was blowing out my number and getting promoted fast. But the moment I missed a quarter, it hit me hard. You start questioning everything.

THE REALITY OF TECH SALES: A CONVERSATION MOST PEOPLE AREN’T HAVING

When Anthony first got into tech sales, he was planning on law school. But after seeing a few six-figure pay stubs from people selling Microsoft software, he pivoted. Started small, did his time at a resale shop, then landed a BDR role at Palo Alto Networks. Within two years, he was clearing six figures and getting promoted like clockwork.

Sounds great, right?

It was. Until it wasn’t.

Because what no one tells you is that early success can be dangerous. When everything comes fast—commission, recognition, titles—you start to believe that’s the baseline. Then your first slow quarter hits, or your big deal slips, and suddenly you’re spiraling. Wondering if you’ve lost it. Questioning if you belong here.

That mental whiplash is what breaks most people. Not the rejection. Not the grind. It’s the volatility.

SALES WILL TEST YOUR MIND, YOUR BANK ACCOUNT, AND YOUR IDENTITY

One of the themes Anthony hit on hard is how easy it is to let lifestyle creep sneak in. You're 25 making $200K and living like the commissions will never stop. But Enterprise deals are slow. One slip, one layoff, and suddenly you’re stressed, scrambling, and overextended.

‍“I was laid off in 2020. It was a massive ego check. But it made me hungrier. It forced me to be more self-aware in how I sell and how I manage myself.”

That’s one of the biggest takeaways: you need margin. Financial margin. Emotional margin. A life outside of sales. Because if your identity is tied 100% to quota, it’s only a matter of time before it catches up to you.

SMB VS. ENTERPRISE: IT’S A DIFFERENT GAME

Anthony also breaks down the shift from SMB and commercial sales to Enterprise. It’s not just a title bump—it’s a completely different rhythm.

In SMB, you can grind and win fast. One or two good champions can get a deal done.

In Enterprise, you might never meet the CTO. You might work an account for a year before you see any money. You’re not just selling to one team—you’re navigating six or seven different teams, all with their own timelines, politics, and priorities.

You need to think in systems, not sprints. You need to learn how to connect the dots across teams and use small wins as leverage to expand. And above all, you need to be patient. Enterprise reps aren’t the loudest—they’re the ones who play the long game better than anyone else.

YOUR INTERNAL BRAND IS MORE IMPORTANT THAN YOU THINK

We talked a lot about this idea that effort doesn’t always show up on the scoreboard right away. Especially in Enterprise. You might only hit 60% of your number one year—but if you’ve built the right pipeline, shown smart plays, and earned trust from leadership, you’re still in a strong position.

The key? Make your progress visible.

Among other things, Anthony suggests sending weekly updates—not noise, but real insights. How many meetings you’ve had. What outcomes are coming. Who you’re multi-threading with. What your pipeline trajectory looks like.

Not because you're trying to cover your ass. But because leadership needs to advocate for you up the chain. Give them something to work with.

MENTAL + PHYSICAL FITNESS ISN’T A NICE-TO-HAVE, IT’S MANDATORY

Sales is a performance business. Full stop.

And the more senior you get, the fewer dopamine hits you get. No one’s hyping you up for cold calling or booking a meeting. You have to generate your own momentum.

For Anthony, that looks like:

• Working out 4–5x/week
  
• Prioritizing sleep
  
• Eating clean (80/20 rule)
  
• Cutting back alcohol
  
• Taking breaks from the grind to reset
  

Sounds simple, but most reps don’t do it. Then they wonder why they’re fried.

MENTORSHIP, ENERGY, AND WHO YOU SURROUND YOURSELF WITH

If you’re going to last in tech sales—truly last, not just survive the next quarter—you need more than a script and a CRM.

You need mentors. People who’ve been where you’re going. Some inside your company who can help you navigate product, process, and politics. Others outside, who’ll challenge your thinking and help you see your blind spots.

But even beyond that, you need the right people around you every day.

As Anthony puts it:

‍The most success I’ve had in the last 4–5 years came when I started surrounding myself with people who are actually positive—professionally and personally.

This industry is full of pressure. Of rejection. Of late-stage deals going dark. And if your closest peers are jaded, cynical, or cutting corners, that energy will rub off—on your mindset, your calls, and your performance.

But when you’re around people who bring energy, ideas, and real belief? That rubs off too.

Sales is a long game. Who you run it with matters.

FAQ

Q: What’s the biggest reason reps burn out after 2–3 years?
A: They don’t build structure around their finances, mental health, and relationships. And they treat early wins like a forever baseline.

Q: How do you make the jump from SMB to Enterprise?
A: Learn to play long-term games. Expand wins across teams. Build political capital. And expect deals to take 9–12 months.

Q: What matters most during a market downturn or layoff cycle?
A: Pipeline progression, internal brand, and external relationships. Keep receipts. Make your work visible. Stay in shape.

Q: What’s one underrated advantage in sales?
A: Being physically and mentally well. It bleeds into your calls, your energy, and how people respond to you.
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→ If you’re an Account Executive looking to take the next step in a successful 10+ year career, join our AE Mastery program. Built for reps who want long-term growth—not burnout.

TL;DR

• Early success can blind you—build real structure early
  
• Enterprise is a slow, political game—play it right
  
• Mental and physical health will make or break your longevity
  
• Your internal brand and mentorship network protect your career
  
• You need margin, patience, and peers who hold you accountable