How to Get Hired in Startup Sales, Thrive, and Become an A-Player

How nice would it be to land a sales job at the next unicorn startup? A lot of people dream of becoming an early employee at a company, gaining equity, and cashing out, either through an IPO or acquisition. But like most dreams, it’s not always glitz and glamor. Startup sales plays by its own set of rules, usually governed by VC-based formulas for growth, and for a front-line employee, working there may seem risky and chaotic at times. Once a startup raises 30-50 million dollars, much of the risk is gone, and if you join after this time, you’ll find at least some semblance of order. Roles will be specialized and there will be clear hierarchical distinctions. Still, there are plenty of opportunities at early-stage startups that have yet to reach this funding amount, but you should use caution and not work at a pre-series C company if you:

  • Don’t want to constantly figure things out on your own
  • Work better in structured environments
  • Prefer a clear and unambiguous company direction

It’s okay if the above bullets apply to you; early-stage startup sales roles aren’t for everyone. Honestly, it’s probably a bad idea for most people. However, if you have a hustler’s mentality, flexibility, and some good old-fashioned luck, success in this role is possible. If you’re ready to take the reins of the next unicorn, here’s a step-by-step process to make it happen:

[bctt tweet="How to thrive in a #sales role at a tech #startup, by @JakeTDunlap"]

1. Get your dream job

A: Fix your resume

Instead of listing out on your résumé everything you've done, highlight the parts of your job or education that are most relevant to the new role, especially if you're switching careers. Talk about what you've accomplished and, instead of simply noting responsibilities, provide numbers to drive your point home.

On average, 250 resumes are submitted per job opening. To set yourself apart and express your personality, write a creative and thoughtful cover letter. And, when culture is king at startups, your personality not only has to show, but it has to match.

[bctt tweet="Write a creative cover letter to accelerate your #jobhunting, says @JakeTDunlap #careers"]

B: Make them want to hire you

Reach out to a founder or sales manager first with a direct message that shows your background and how you align with the company and culture. Leaders love it when a person takes the first step by reaching out directly. They view it as a sign that this person won't be scared to do so in the future. Sure, they may direct you to HR, but they'll remember you. With that said, I promise that your application-to-interview ratio will shoot through the roof.

2. Thrive in the role

C: Manage up

At an early-stage startup, the likelihood of someone checking your work thoroughly every day is slim. Which means that the probability of you going off-track from responsibilities and goals the leadership sets for you is higher. 

Many front-line and middle managers look at their leaders and say, “They’re busy and I don’t want to bother them, so I’ll just figure it out.” By default, this isn’t a bad attitude, but over time it can lead to wasted time and toxic conflicts. If your direct leader isn’t scheduling enough time to discuss problems and strategies, then it’s up to you to manage up and schedule time with them.

[bctt tweet="#Salespeople—schedule time with your manager to make sure you're on-track, says @JakeTDunlap "]

D: Lose the saying “it’s not my job”

It can seem exciting and interesting to have a job that changes from day to day but, for some people, it can get old after a while and even lead to burnout.

At an early-stage startup, you'll have to handle tasks that are complementary to the role you initially applied to. You shouldn't be doing something completely different every day, but you should expect to take on some tasks that weren’t part of the original job description.

If you aren’t ready to focus your time on more than one task, skip the early-stage startup.

3. Become an A-player

E: Stop thinking like a contributor and start thinking like a leader

If you want to thrive in a startup sales job, you have to think like a leader and not an individual contributor. Take responsibility for the success of the project and not just the work you put in. Effort is important, but emphasis must also be placed on getting the job done right. Even if you spend three hours on a project and then realize you went down the wrong path, don't turn it in. Start over and get it right. Don’t believe it’s someone else’s job to finish or polish your work. [bctt tweet="#Leadership is taking responsibility for the whole project, not just your part, says @JakeTDunlap"]

That’s how to act like a leader even when you may not actually lead or manage people yet. Of course, there’s a point where efficiency and perfection need to be on prioritized on the same level, but taking care of your responsibilities at the highest level possible is never a bad thing.

F: Take ownership everywhere

There is a saying that all great leaders live by because it helps them practice ownership in life:

The true test of a man’s character is what he does when no one is watching. —John Wooden

Pick that napkin up off the floor. Make the next pot of coffee. You make a choice to take pride in your company and your role when you do the things you should do when no one else is around. Take ownership everywhere and it will pay off with big dividends in your role down the road. [bctt tweet="Take #ownership everywhere, even when no-one is watching, says @JakeTDunlap #leadership "]

G: Repeat steps C-F daily

Success in sales for startups can feel very different when compared to success in the more insulated environment of a big company. Much of your growth will come from the experiences you’ll have outside of day-to-day responsibilities. You will see a change in your interpersonal skills and your ability to lead and take ownership, all from doing more than you thought you could ever handle.

These hard lessons will make you much more effective, allowing you to shoot past your peers over the course of your career. What you learn will differentiate you from mid-level employees because you’ll have the ability to think like an owner. Again, it’s not for everyone, but if you're ready, you can thrive by acting like a leader before you ever get there.

[bctt tweet="The lessons you'll learn at #startups will set you apart, says @JakeTDunlap #leadership "]

If, after all this, you still want to join an early-stage sales team, then keep this last piece of anecdotal advice in mind. Personally, I know that before the age of 28 I probably would've been a terrible addition to an early-stage company because none of the points above were as honed as they should have been. Spending a couple of years at a larger company where you're given formal training and structure will give you the experience necessary to tackle your role later on at an early-stage startup. When timing and skills are matched, it'll be a good fit for both sides.

Good luck and let me know how the journey unfolds.

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Jake Dunlap is a senior-level sales executive and entrepreneur with 12 years of experience working with global 2000 and startup companies. Jake is the CEO and founder of Skaled, a consulting firm that accelerates sales organization growth by examining fundamental sales processes and using cutting edge technology to enable clients to optimize, modernize, and thrive in the constantly evolving world of SMB & Enterprise sales. He is also an instructor in our NYC sales and account management course.