Hunt #16: How to select the "right" company?

Good morning hunters!

Four months into this journey, it’s become clear that salespeople have few credible resources to help them level up their interview game. Many are left navigating the job search alone, unsure how to stand out and land the right role.

That’s why we’re stepping up to the plate. The Pursuit Report is evolving. Alongside our day-in-the-life stories, we’ll now be serving up actionable tips and strategies to help you capture the attention of top companies and turn those interviews into offers.

This week, in Hunt #16, we’re diving into how you can spot the real opportunities from the pretenders. Let’s dig in!

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Introduction

Deciding to interview with a company can feel like a big gamble. You’re putting your time, energy, and reputation on the line. So, how do you know which companies are worth your time and effort?

While I believe that salespeople should always be open to interviewing—even if you’re not looking to switch—keeping your skills sharp, growing your network, and adding data points for when you find that A+ company is invaluable. However, there are definitely companies that aren’t worth your time, and that's where a quick sniff test can save you a lot of frustration.

I recently spoke with a salesperson who wanted my take on a company that had approached them directly. Here’s the 4-step process I used to evaluate the opportunity in less than 10 minutes. Hopefully, this helps you avoid making an unforced career error!

My four step process w/ examples

Step 1: Check Their Longevity and Momentum

The first thing to assess is how long the company has been in business and what their growth trajectory looks like. Are they scaling steadily, or are they struggling to gain traction?

• Example: This particular company has been around for almost a decade but is only hitting ~$5 million in annual recurring revenue (ARR). If they were bootstrapped, this might be understandable, but they’re VC-backed! What’s more, my tiny recruiting startup has more LinkedIn followers than they do. This lack of momentum and presence doesn’t bode well.

• Verdict: Strike 1

Step 2: Assess the Leadership Team’s Talent

A company's leadership can make or break a company. Look at the backgrounds of the CEO & C-suite and deep dive on who’s leading the sales team. No matter how good you are…you cannot win if your leadership team doesn’t have the right experience and vision to navigate challenges and support you & the sales org effectively.

• Example: This company is led by a second-time CEO who has never scaled a business beyond 40 employees. The Head of Customer Success has no prior relevant experience, and the SDR Leader, with < 200 LinkedIn connections, has zero background in sales development. Worst of all, they haven’t had a true sales leader for years, and this position reports directly to the CEO—a clear sign of disarray.

• Verdict: Strike 2

Step 3: Consider the Product and Market

Is the product exciting, and is the industry booming? Most importantly, will a future employer look at your experience and say, “I need you on my team because you worked there”?

• Example: This company’s product isn’t in a hot industry, doesn’t seem to be a ‘must-have,’ and targets a persona that probably isn’t eager to change their workflows or adopt new technology. It’s not the kind of experience that will likely stand out on your résumé in a positive way.

• Verdict: Strike 3

Step 4: Evaluate the Tenure and Talent of Past Salespeople

This might be the most telling sign of all. Check the track record of their sales team. How long have they stayed, and where have they gone?

• Example: The company currently has only one salesperson, an SDR, and only one person has lasted longer than a year in any sales role—and just barely. For a company this old, this turnover rate is a glaring red flag that should make anyone think twice.

• Verdict: Knockout punch!

Final Thoughts

There’s nothing worse than joining a company you instantly regret. Take your time to evaluate opportunities upfront, especially when a company reaches out to you first. It could save you from a lot of pain, wasted time, and unnecessary stress.

Remember, there’s no way to get every career decision right, and sometimes you have to take a calculated risk. But if you’re going to place a bet on your career, make sure it’s on a company that has more than just a good pitch. Do your homework and place your bets wisely.

Thanks for reading, and I hope this helps you make smarter career moves!

That’s all for this week. Feel free to reply with any questions or feedback. Happy hunting!

Jay Green “The Quota Hunter”