Break Into Tech Sales
By: Mike Basso – January 4th, 2026
Two Proven Paths To Break Into Tech Sales (And Why Most People Fail)
I get asked all the time, “Mike, how do I break into tech sales?”
And I already know what’s coming next.
Someone is going to tell me they’ve applied to 200 jobs. Someone else is going to tell me they’re “networking” but all that really means is clicking “connect” on LinkedIn and hoping a recruiter shows up like the Tooth Fairy.
Allow me to save you a bunch of time.
If you’re trying to break into tech sales by blasting resumes into a black hole, you’re playing the wrong game.
Tech sales hiring is not a raffle.
It’s pattern matching.
Hiring managers are looking for a tight fit. Recruiters are scanning for clues that you match the role they were briefed on. The more your background looks like the last person who crushed it in that seat, the faster you move. Learn More by reading Become a Recruiter Magnet by Mike Basso
So when people ask me how to break in, my answer depends on who is asking.
There are two proven paths I’ve consistently seen work over and over again.
One is the traditional climb. The other is the industry crossover.
Both can get you into a high six-figure career. Both can lead to serious long-term upside.
Neither is magic.
And both require you to stop acting like a job seeker and start acting like a seller.
First, a quick reality check on “tech sales”
Tech sales is not one job.
It’s a stack of roles and segments.
You might start as an SDR (sales development rep) or BDR (business development rep). That’s lead generation and meeting setting. You’re learning outbound. You’re building call confidence. You’re getting punched in the face by rejection until it stops hurting.
Then you move to AE (account executive). That’s full-cycle selling. Discovery. Demos. Negotiation. Closing. Owning a number.
From there, most careers ladder through segments:
* SMB: faster cycles, higher volume, smaller deal sizes.
* Mid-market: more stakeholders, more process, bigger deals.
* Enterprise: longer cycles, higher complexity, bigger wins, bigger losses.
That’s the playing field.
Now let’s talk about the two paths.
Path 1: The Traditional Climb
This is the cleanest route if you’re starting from scratch.
It’s not the only route.
But it’s predictable.
Step 1: Build a foundation that employers respect
A four-year degree in business, marketing, or sales helps. If your school has a sales program, even better.
No degree? You’re not dead.
You just need a different form of proof. We’ll get to that.
Step 2: Get close to SaaS early
If you’re in college, get an internship at a SaaS company.
In addition to gaining experience, the internship is a long audition and should be treated as such.
Show up on time. Ask smart questions. Volunteer for the hard stuff. Be the intern who actually finishes tasks without needing three reminders.
Interns get hired.
Not because they’re interns.
Because hiring managers love reducing risk.
Step 3: Start as an SDR, and treat it like paid training
SDR work is the front line.
It’s not glamorous. It’s not supposed to be.
You’re learning the hardest part of sales: creating demand when none exists yet.
You learn how to:
* Write outreach that gets replies
* Call strangers without coming across as like a hostage
* Ask questions that earn time on the calendar
* Handle “not interested” without spiraling
If you can do that, you can sell.
“But Mike, how do I get hired as an SDR with no experience?”
You build proof.
Not a “passion for sales” statement. Real proof.
Here are a few ways to do it:
1) Build a target list like a real SDR would.
Pick 25 companies. Pick one role you want. Build a spreadsheet with:
* Company
* Segment (SMB, mid-market, enterprise)
* Product category
* Who the SDR manager is
* Who the AEs are
* Why you fit
2) Build a mini outbound sequence.
Write:
* One cold email
* One LinkedIn outreach
* One call opener
* Two follow-up messages
Keep it simple. Sound like a human.
3) Practice call blocks.
You don’t need a dialer to practice. You need reps.
Record yourself doing a 30-second opener. Listen to it. Fix it. Do it again.
Most candidates won’t do any of this.
That’s why it works.
Step 4: Earn the AE promotion
Most strong SDRs can get promoted in 12 to 18 months.
But here’s what controls that timeline:
* The company’s growth (are there AE seats opening?)
* Your numbers (are you actually producing pipeline?)
* Your attitude (are you coachable or a complainer?)
* Your skill progression (do you run tight discovery, or do you just set meetings?)
If you want the fastest path, act like an AE before you get the title.
Listen to sales calls. Ask to shadow demos. Learn the product well enough to speak in outcomes, not features.
And one more thing.
Learn the language of numbers.
Top sellers know their metrics cold. Quota, attainment, win rate, ACV, cycle length. If you can’t speak that language, you sound like a passenger.
Step 5: Move up-market over time
Once you’re closing deals, your next leap is usually deal size and complexity.
SMB teaches speed.
Mid-market teaches multi-threading.
Enterprise imparts patience, planning, and political navigation.
If you’re good, your earning power expands fast.
And yes, the upside can be life-changing.
But you earn it by becoming a real operator, not a title chaser.
Path 2: The Industry Crossover
This is the path most people miss.
And it’s the fastest route for experienced sellers who are stuck outside of tech looking in.
Here’s the idea.
If you already sell into an industry, target tech companies that sell to the same industry.
You already speak the buyer’s language.
You already know the pain points.
You already understand how decisions get made.
That’s not a small advantage.
It’s a cheat code.
Step 1: Sell to the same customer, just with a different product
Most people try to “break into tech” by applying to random SaaS companies.
That’s why they get ignored.
Instead, do this:
- Write down the industry you’ve been selling into.
- Write down the buyer you sell to.
- Then target tech companies that sell to that same buyer.
You’re not starting over.
You’re switching vehicles.
Examples (so you can feel it)
- Sold medical devices into hospitals? Go sell healthcare software.
- Sold logistics services? Go sell supply chain tech.
- Sold payroll or benefits? Go sell HR tech.
- Sold into banks? Go sell fintech.
When you do this, you’re not “breaking into tech.”
You’re bringing a tech company a rep who can ramp faster because you already understand the customer.
Step 2: Use your domain credibility to shorten the ramp
Tech companies don’t just buy selling skill.
They buy speed.
If you know how the buyer thinks, you can:
- Ask better questions in discovery.
- Call out real-world landmines before the deal blows up.
- Navigate procurement without acting surprised that it exists.
- Sound credible on day one, not month six.
That reduces risk.
And when you reduce risk, doors open.
Step 3: Target roles where you can often skip SDR
The big win with Path 2 is you can often skip the SDR stage.
Not always.
But often.
Here’s what you need to show to be taken seriously for an AE role:
- You can hunt for new business.
- You’ve carried a quota.
- You can run a sales cycle, not just “support” one.
- You’ve sold into the same buyer persona.
If your background hits those points, you have a real argument.
And you should make it directly.
Quick gut-check: are you really an AE candidate?
If most of your wins came from inbound leads, renewals, or existing accounts, you might still be asked to start in SDR.
That’s not an insult.
It’s a signal that you need more outbound proof.
Step 4: If they push you toward SDR, don’t panic
Some companies will still push you toward SDR even if you have closing experience.
If that happens, stay calm.
Do not argue.
Just ask this:
“Is this role designed to promote to AE in 12 to 18 months, and what percentage of SDRs actually make that move here?”
Then shut up.
Let them answer.
If they dodge, that tells you what you need to know.
If they give you clear numbers and a clear process, it might be worth it.
Step 5: Build proof that you can sell in a SaaS motion
Even with strong industry experience, you still need to show you can operate inside a modern SaaS sales process.
Here are a few simple ways to do that:
- Translate your numbers into SaaS language: quota, attainment, average deal size, cycle length, win rate, and your rank on the team.
- Map your buyer journey: who signs, who blocks, who influences, and how budgets actually get approved.
- Create a short “crossover pitch”: 6 to 8 sentences that explain why your industry background makes you a faster, safer hire.
- Bring a 30-60-90 plan to interviews: not fluffy goals, real actions and target accounts.
Most career switchers show up with hope.
Show up with receipts.
That’s how you get into tech faster.
Conclusion
Breaking into tech sales comes down to focus and proof. Pick the path that matches where you are today. If you’re early-career, take the traditional climb and stack reps fast. If you’re already selling, use the industry crossover and target tech companies that sell to the buyers you already know. Make the fit obvious on your resume, LinkedIn, and in every conversation. Bring numbers. Bring examples. Bring a plan. Run this like a sales cycle, not a job hunt. If you stay consistent, the market will eventually meet you halfway.
Mike’s expert advice on sales recruiting and hiring is regularly quoted in media outlets such as Newsweek, Business Insider, MSN, AOL, Nasdaq, Yahoo Finance, Monster.com, HubSpot's Sales Blog, Jobscan, Jobvite, JazzHR, and many more. You can learn more about Mike Basso by visiting linkedin.com/in/salestalent/
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