This honest guide helps career changers and aspiring SDRs evaluate if tech sales is the right move by breaking down the real risks, rewards, and mindset shifts needed to succeed long term in a high-pressure, high-reward B2B sales career.
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Tech sales can be life-changing, but it’s not for everyone. In this post, I’m pulling back the curtain on my personal journey: how I transitioned out of engineering, why I chose sales, and what most people don't understand about the long-term path. If you’re considering breaking into tech sales, this is your gut check.
This post is especially for aspiring SDRs and career changers who are evaluating if tech sales is the right move or just chasing the hype.
Tech sales gets hyped as the fast lane to high income, and sometimes it is. But too many people jump in without understanding the stress, rejection, and long ramp-up it takes to succeed. The internet is full of six-figure screenshots and “quit my job” stories. But what happens after year one?
"In the first four years, I quadrupled my income. But it wasn’t all sunshine. It was stressful. And most people don’t see that side of the game.”
Whether you’re coming from another field or just starting out, this post will help you evaluate if tech sales is truly aligned with what you want and how to set yourself up for long-term success if it is.
I started my career as an engineer at a respected Fortune 1000 company. On paper, it was everything I wanted. But six months in, I knew it wasn’t a fit. I was coming from a performance-driven environment as a student-athlete and Team USA handball player where effort equaled reward. In corporate engineering, that feedback loop was gone. Regardless of how hard I worked, I was paid and rewarded more or less the same. I was no longer in a position where my direct performance impacted my outcome.
What finally pushed me out? A promotion I was promised didn’t come through. The feedback I got contradicted months of praise. When I challenged it with direct quotes, my manager admitted he had “forgotten” about the incidents I brought up. That was the breaking point.
The deeper issue was that I couldn’t stomach the idea of putting in years of work for capped upside. I wanted ownership over my outcomes, even if it came with risk. I would rather make the same amount of money with the stress of sales as opposed to being mentally checked out every day and doing the bare minimum.
If you want guaranteed stability, tech sales is not for you.
The best reps can make big money ($500k or more). But it is volatile. I’ve seen people get laid off in their first year. Others quit after a bad year. Others have had a great year and by the end of the following year are let go. The upside is real, but so is the pressure.
What helped me stay in the game was having a long-term mindset. I wasn’t trying to blow up in six months. I was playing for year five, not month five. While you can make great money in year one and two, the real upside comes from sticking it out for ~3-4 years. That is where you go from making ~$150k to ~$250k+, and life can change pretty quickly.
Let’s be honest. Money is a great reason to get into sales. I did it too. In January 2025 I made $70,000; more than I did an entire year as an engineer. But that excitement fades over time. It's incredible to get a $50,000 check, but it's a lot easier to grind every day when you have nothing in the bank compared to when you have a comfortable nest egg.
What keeps you going is how you use that money. For me, saving aggressively gave me peace of mind. It meant I didn’t need to close every deal. I wasn’t desperate. That helped me sell better.
If you’re getting in just to buy a new car or show off on social media, fine. But that motivation won’t last, and the insane money motivation you have when you first start will fade as you get more comfortability and your lifestyle inflates.
I had no sales experience when I broke in. What I did have was an entrepreneurial itch. It's why I started Higher Levels on nights and weekends when my career started taking off. Before that, I had started a small coffee business, consumed sales content constantly, and wasn’t afraid to try and fail.
That’s the pattern I see in students who break in and actually stick.
If you’re already listening to business podcasts, testing ideas, or freelancing—even if it’s not working yet—you’re probably wired for sales.
One student Michael that I coached had no job for two years after graduating college but spent that time trying to build a UI/UX consulting business. Even though they didn't grow it to be a sustainable business, the lessons they learned and skills they developed showed coachability and grit. In Michael's own words:
I thought my lack of corporate and tech experience would prevent me from being successful, but I ended up landing interviews with more than half of the companies I applied for.
They got hired at one of the top unicorn companies in Silicon Valley that recently went public (you can see Michael's story here).
You don’t need to be a tech expert. But if you can’t bring yourself to read a whitepaper, watch a product demo, or study a company before an interview, this probably isn’t the right fit.
Saying you’re into tech because you like apps or Chrome extensions is not enough. You are selling technical products to serious buyers. If you can’t engage with the product, you won’t last.
One of the biggest advantages I had was knowing I didn’t want to stay where I was. That clarity gave me permission to take the leap, even if it meant starting over.
If you’re in a job that pays OK but doesn’t energize you and you are willing to trade short-term comfort for long-term upside, that’s a great sign.
Just don’t wait too long. I knew a year in that I should leave engineering. It took me two more years and a year abroad before I finally made the jump. I wish I had done it sooner.
Q: Is it OK to get into tech sales just for the money?
A: Yes, if you are honest about it and plan for long-term goals. Just don’t let that be your only motivator.
Q: Can I break into tech sales without experience?
A: Absolutely. What matters more is your ability to learn fast, take feedback, and drive outcomes.
Q: What makes someone successful in tech sales?
A: Grit, coachability, genuine interest in performance-based work, and the ability to manage pressure.
Q: How long does it take to really succeed in tech sales?
A: The biggest jump in upside comes between years ~three and five. Year one is just the foundation.
Q: What’s one mistake to avoid?
A: Jumping in because it looks cool without understanding the stress, rejection, and grind it takes to win.
If you’re serious about breaking into tech sales and want direct coaching, a clear plan, and real support, join our Tech Sales Ascension program. It’s built for career changers who are done overthinking and ready to land the role.
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