5 Ways To Jumpstart Your Sales Career at a Startup

There’s a shift going on in our perception of career success. We’ve swapped out the stability and upward mobility associated with jobs at big-name companies for startup opportunities. Startups are now viewed as the keys to faster success. And many of the available jobs in startups are in sales.

The problem is that, contrary to popular belief, sales is not some secret back-door to instant success at a startup. I’ve talked to many non-sales executives about this, and their go-to response is, “Sales is a great place to break into an organization. I tried sales and wasn’t very good at it, but it gave me great experience.”

Let’s focus on the second part of that statement. Many people give sales a try and fail miserably. And at many startups, having this kind of failure can be crushing, especially if it involves your early hires.

Why do people fail at sales? After all, there are plenty of smart, well-rounded individuals out there who should be able to “figure it out.” The answer is: commitment. If you aren’t 100% committed to being the best sales professional you can be, you’ll rarely be successful.

So if you’re a startup, if someone says they want to “do sales for a little while” and then move into a different role…run. Sales is all about perfecting the craft over time, and if someone isn’t ready to commit fully to the mentality, then they’re not worth your time.

Candidates: Assuming you’re ready to commit to a career in sales, how do you use a startup to drive success for both you and the company? Here are the musts:

1. Work at a larger company first

You need to learn a replicable process, as well as how to utilize key systems like Salesforce and Linkedin that are essential for sales. Chances are, you won’t get the hands-on help you may need at a 50-person (or 20-person) startup. So work at a larger organization first, one that has a formalized training program and onboarding plan. Not only will you be more confident in your next role, but you’ll also be able to introduce the good pieces of the process to your new company.

2. Expect to help build the process

As a part of the original (most likely small) sales team at a startup, you’ll enter in the “figuring it out” phase. If your company doesn’t have a VP of Sales (and even if it does), you’ll need to be proactive and not expect the type of oversight and system structure that you had at a larger company. Make sure you really want that type of environment from the start, and when you get the job, start building out the systems you know a company will need to be successful. It’s a great feeling to know that you’ve helped create the structure that others are using — plus your work yields invaluable experience for future roles.

3. Don’t only use job sites to apply

Sales leaders and CEOs want to see that you want it. Do five minutes worth of research on the company (and on the person that you plan on contacting), then reach out via email and call with a relevant reason for why their needs fit your skills. Sales leaders have egos so find a relevant article or place where they are featured.  This separates you from the mass amounts of applications coming in from recruiters or from the HR department. It shows that you know what to say to a decision maker, and how to say it.

4. Bring something tangible to the interview

In my first three roles in sales, I prepared a 30-60-90-day plan to bring to the interview. Each plan included company-specific scenarios, as well as viable alternatives to those scenarios. When I applied for a job with the Phoenix Coyotes, I was flown in for a group interview with 35 other salespeople from across the country. I was the only person who brought a plan on how to position the Coyotes and sell hockey in Arizona. Instead of the typical interview questions, we discussed my plan, the issues with it, and the areas that would work. I got the job, and am confident that my plan helped separate me from the slew of other candidates. Come prepared…don’t just show up.

5. Don’t make lateral moves

This is key. Don’t take a role at a startup that’s similar to your current role, unless the opportunity is undeniable. You’ll most likely get a boss, and will be relegated to the same middle management role that you would have had at your current company.

Instead, wait another year and take the promotion at your current company. You can then come into a sales leadership role directly. If you’re a leader at a big company and then want to join a startup a year or two later, you can typically enter at a higher level.

As with all rules, there are exceptions. But my experience of hiring (and firing) hundreds of sales reps has convinced me that these are the biggest takeaways in deciding whether or not to move to a startup.

Bottom line: A career in sales requires commitment and self-awareness. You must ensure that the situation is right for you, regardless of how it looks on paper. Working in sales at a startup is not easy, so if you decide to go down that path, make sure you’re taking on a role that you truly want.