Ben Orenstein of Tuple


Today, I’m talking with Ben Orenstein, a co-founder of Tuple, the best remote pair-programming app on macOS, and co-host of The Art of Product Podcast.

Ben was a developer at thoughtbot but left to start Tuple to fill the gap in the remote pair-programming market after Slack shut down Screenhero.

They launched just two years ago and in that time have grown to a place where the 3 co-founders have all replaced their developer salaries and are able to build out their team. They’ve done all of this while remaining bootstrapped and profitable and their growth is accelerating from here.

In our chat, we dig into Ben’s evolving role as CEO and focus on two crucial topics: how he developed his enterprise sales skills, landing huge clients like Shopify, and how he’s navigating the challenges of hiring.

I was introduced to Ben by a previous guest of the show, Matt Wensing of Summit, and I’m glad he connected us because we had a great conversation that you won’t want to miss.

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Topics covered:

  1. Company background
    1. What exactly is Tuple and what does the business look like today?
  2. Founder’s lessons
    1. How would you describe your role today?
    2. How have you developed your sales skills?
    3. What’s your plan for making a new sales hire?
    4. How do you approach hiring in general?
  3. Behind-the-scenes
    1. What has been the hardest part of building the business for you personally?
    2. What does success look like to you?
  4. “Rapid Fire” questions
  5. Where can listeners go to learn more?

Resources mentioned:

Where to learn more:

To hear more from Ben you can check out The Art of Product Podcast or follow him on Twitter.