How to Get a Startup Sales Job

Quick: What’s the biggest thing standing between you and a hot startup sales job?

A weak resume?

Boring cover letter?

Uninspired LinkedIn profile?



Secret 1: Know Thy Customer

Stop thinking like a job applicant and start thinking like the ace salesperson you are: What’s the cardinal rule of sales?

Know thy customer.

And so the first secret to startup hiring success is to understand precisely who your customer is for this particular “sale” (i.e., the one with you as the product!).

Let me give you a hint:

It’s not your career counselor, who’s always telling you to make sure all your resume bullets are in the active voice.

It’s not your proofreading buddy, who’s always catching little typos in your cover letters.

And it’s not even all those random people on LinkedIn who keep looking at your profile.

No, your only customer is the hiring manager at that hot startup you’d love to work at. And chances are, she doesn’t really care about your resume, cover letter, or LinkedIn profile.

After all, how many customers do you know who buy 5 or 6-figure products based solely on the sales collateral?


Secret 2: Hiring Process = Sales Process

So if all the things you thought mattered don’t, what actually does?

To understand what your hiring manager “customer” really cares about, let me give you a glimpse into how I hired sales devs at an edtech startup with $10MM+ in VC funding.

Which means grasping the second secret of startup sales hiring: How perfectly the hiring process aligns with the sales process. In other words, everything you do as a job applicant – from introducing yourself via a cold email to closing the deal with a final presentation – directly mirrors what you’d have to do as an actual sales rep. And so whereas hiring coders is really tricky (i.e., just because someone can write an algorithm on a whiteboard in 10 minutes doesn’t mean they’ll be a workhorse in the crazy 10 weeks before launch), hiring for sales is basically a “What you see is what you get” deal.

Now what that means for you, the applicant, is that you should view every part of the application process as a real-world sales audition. So instead of spending months perfecting your resume (which is really more of a marketing function when you think about it), spend that time on top-of-the-funnel hustling.

For example, our very first Sales Dev hire was only 19 years-old. And while his resume was both sparse and unpolished, he hounded us for weeks with emails and just flat-out hustle. Which is exactly the kind of moxie we needed to launch a brand-new product category in an old-school industry like education.

So don’t be afraid to go hard after startups you’re passionate about. Because all that hustle isn’t just in pursuit of an interview; it’s actually the first real proof that you can do this crazy tough job.


Secret 3: Seeing Is Believing

So you’ve hustled and hustled – and you’ve finally been rewarded with an interview at that awesome startup. Time to start practicing your standard interview answers (“I’d say my biggest weakness is I work too hard…”), right?


Because even though those kinds of answers may be typical fare for big companies, startups don’t have time for that fluff. They need someone who can come in and hit the ground running. And so, even if they ask some basic questions to get started, know that the only thing that matters is the roleplay.


Because seeing is believing. Because anyone can learn to recite BS answers to BS questions, but great sales skills can’t be faked. Because either you’re going to stand strong in the face of cold call resistance or you’re going to quiver like the Golden Gate in a windstorm.

So how do you make sure you ace the roleplay? Do you have to memorize everything about the startup’s product? Or build a mental rolodex of their entire client list???

While knowledge in all of those areas certainly can’t hurt, I knew it wasn’t fair to judge my interviewees on that kind of insider info. So instead, I always focused on three skills that had nothing to do with my specific company or product – but that are hallmarks of sales greatness everywhere:


1.     Do they ask questions?
So many candidates are so nervous in interviews that they practically start their pitch before the interviewer can even lay out the roleplay scenario. Which, of course, is a recipe for failure in a world where sales are based on relationships, not pure speed!

2.     Do they actually listen to the answers?
Slightly savvier candidates will remember to ask questions – but then they’ll robotically go into their pitch two minutes later with no reference to any of the information the interviewer has shared with them. Again, no one wants to buy from a robot, so listening and personalization are key.

3.     Do they persist in the face of pushback?
Even thoughtful candidates can stumble at the end when, inevitably, the interviewer comes up with some reason to turn down their offer of a demo. And so that’s where a sales superstar can really stand out – by firmly, but respectfully, continuing to push even in the face of adversity.


So as you prep for your interviews, don’t sweat the clichéd questions and answers. Instead, focus on the real thing: Can you do the job that needs to be done? Can you interview prospects, tailor proposals, and persevere when the going gets tough?

Because if you can do all those things, the job is practically yours. After all, when it comes to sales, seeing is, indeed, believing.


How to Actually Get a Startup Sales Job

So there you go. Startup sales hiring is like no other talent search on earth. Instead of sweating resumes and cover letters, focus on your customer. Instead of pruning your social media profiles, hustle like you would to generate prospects. And instead of practicing 100 irrelevant interview questions, focus on the three parts of the interview that actually predict your job performance.

Because when you do so, you’ll make your customer very happy. And you’ll close the most important deal of your career!



Click here to get a free guide to the exact interview techniques I used to land tech and startup jobs.