What to Consider When Selecting Your Next Sales Role

Here’s the good news for sales professionals: there are over 14 million gainfully employed in the United States, and the demand for sales professionals is staggering.

That’s no surprise: a salesforce is the lifeline of almost any company, and thus a high-performing salesperson is one of the most indispensable assets an organization can possess. As you would expect to follow, unemployment amongst salespeople has been estimated as low as 4.4%. Indeed, there are nearly 850,000 sales openings right now on LinkedIn alone.

The bad news, however, is that like any other function, finding your ideal position as a salesperson is no easy task. Unreasonably high or constantly changing quotas and activity expectations, feeling weighed down by the daily grind of meeting numbers, lack of autonomy, a poor product-market fit, a dull or uninspiring, or, even worse, detrimental product you are tasked to sell are all potential pitfalls that could, over time, crush the morale of even the most spirited salesperson.

As you navigate your career path, chances are the first job you take will not be the ideal fit. Contrary to popular belief, employees do stay in their same job longer today than they did 10, 20, even 30 years ago.

However, this doesn’t mean that as you build a track record for yourself, or even at the outset of your career, that an educated and polished salesperson, perhaps one that has gone through the Victory Lap program, is without optionality. We all know there are many companies HQ’d in the Bay Area and elsewhere famed for their lavish employee experience.

So what should guide your decision about what’s the best fit? See below.


There’s an old adage in sales, “if you don’t believe in what you’re selling, neither will your prospect.”

This saying really could not ring more true. Think about it: sales is really about demonstrating to your prospect how your product or service will solve a challenge for them, or make their lives or easier in some way. If you don’t believe that it will, how could your prospects possibly come to that conclusion? Furthermore, anyone who has worked in sales long enough knows it can have its ups and downs. When you’re experiencing a bad stretch, and people aren’t calling you back, at times the only thing you have to lean into is your belief that you are doing good work by representing your company on the front lines.

So write down some ideas that inspire you. Simon Sinek poses the question, “Why do you get up in the morning? Why should anyone care?” Maybe your mom or dad owned a small business growing up, and you want to help small businesses? Google, for example, helps level the playing field for small businesses by making advertising about relevance, not just resources. Perhaps you are a former educator passionate about closing the achievement gap? ThinkCERCA, my company, and many other education technology companies have a place for you.


If you are hellbent on taking a big risk and moving across the country to work for a promising startup, with the lure of equity, free meals and brilliant coworkers, I don’t blame you. I actually did it on more than one occasion.

What you should know though, is with great reward potential comes great uncertainty. Always expect the unexpected.

Case in point: I arrived in San Francisco in September of 2014 at a company of ~80 employees that employed just five in my position. Experiencing tremendous growth and a strong product-market fit, by the time I left in February 2016, the number of employees had doubled overall and tripled in my position. A few months later, I found out due to a tough stretch, a considerable percentage of the sales team was laid off. If I had stayed, I would have found myself living in the most expensive city in the country, desperate for a new role.

These are the stories the headlines of “unicorns” and “rapid growth” don’t exactly tell, but they play out all the time. In a startup, typically you are asked to trade stability and certainty for extra responsibility, excitement, ownership and autonomy. And that’s certainly, in my opinion, a worthwhile trade-off. But it’s a calculus you need to seriously consider before deciding it’s the right path for you.


Do you get a certain thrill from tying a double windsor knot before a big meeting? Or would you rather make jeans and sneakers Friday every day?

Do you want someone to tell you exactly how to do your job, how many calls to hit every day, and know that hitting your number is your sole responsibility, or would you prefer autonomy, no activity targets, and the possibility to write blog posts, head up a volunteer effort, or work cross-functionally in addition to your day-to-day responsibilities?

Does the idea of participating in Margarita Monday after work every few weeks to “get to know the team” excite you or give you anxiety?

These are all important considerations for what type of company culture you will thrive in.

For me, a guarantee of autonomy, along with connecting with the company’s mission, has been my most sought-after aspect when evaluating a new role. If I believe in the company mission, and I feel empowered by management to focus on output and my job, without specific orders on how to get it done, that is ideal. Others may feel if they’re not given specifications for how to go about the job, they feel uneasy and unstructured.

Ultimately, finding the best fit takes a lot of work and might not happen the first time. It goes beyond asking in an interview setting, “What is the company culture here?” It’s digging into the real questions and taking time to connect with current employees to find out the type of people that thrive and those that don’t. What will be expected of you? How much do you want to contribute, and will that be possible? Do you truly believe in the organization’s mission?

Remember, Steve Jobs said, “The only way to do great work is to love what you do.”

Jared Hocking | District Partnerships Manager, ThinkCERCA

Jared Hocking