An interview with Ben Stewart, who runs the r/techsales subreddit

When we think of sales communities, it’s usually LinkedIn or Facebook that come to mind. But when it comes to discussion sites, reddit reigns supreme. We wanted to learn more about the conversations that take place on the wildly popular site, so we reached out to Ben Stewart, who runs the r/techsales subreddit. Ben has been in the tech sales industry for the last 10+ years working for various startups and Fortune 100s and is also the founder and CEO of (note: the following interview has been edited for length and clarity) 

How did you get your start in sales? When did you know that it would be your career?

I started in sales straight out of college even though I graduated with a business degree in finance. When I first started in a Sales Development Rep role, I didn't really know if it would be for me, but once I made the jump to Account Executive, I started to realize that I was pretty good at it. It was after I started making decent money when I realized I could see a future in it as well as the opportunity to help others in the process.

You run r/techsales on Reddit. Why did you decide to start the community? How has it grown?

There was a point in my sales career when I was leading a large team of tech sales reps, and the most satisfaction I got in that role was when I helped these reps get promoted off my team and into bigger and better roles. By starting a community, I realized I could help more people learn about this career path and achieve success. Since September, we’ve grown over 300% and I hope to continue that trajectory.

There are a ton of sales communities out there, but Reddit is unique because it allows people to be anonymous. How do you think this affects the way people communicate and engage with each other when discussing sales?

The beauty of Reddit is the fact that all users in a community can upvote or downvote any comment. This enables self-policing within the group, which ensures that better comments rise to the top while the others fall off. This gives users better information without having to sift through so much content.

What's one thing you've learned about salespeople from running your community?

We are a competitive yet generous bunch. The information sharing has been incredible which really helps new (and old) reps learn and grow.

What is the state of tech sales these days? What are you seeing out there?

After coming off a record 2021, sales were slow in the second half of 2022. We saw a lot of PIPs and reps getting laid off as well as comp changes at various startups. That being said, we’re starting to see upticks in hiring and corporate spend ticking up already, so I'm optimistic for the future.

How would someone who wants to break into tech sales get started? What would you recommend?

I actually wrote a blog post on this topic but if I were to break it down it would be this:

1. Find companies hiring SDRs.

2. Narrow down those companies by products you can get passionate about, sell well, and are a "need to have."

3. Start reaching out to anyone and everyone who might be able to help you get your foot in the door at those companies and ask for help.

4. Don't give up, it's a numbers game.

What's your favorite sales movie?

The Wolf of Wall Street

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