The Future of Software Sales: What to Expect Over the Next 5 Years

Imagine it’s the year 2026. You’re the founder and CEO of a fabulously successful SaaS company, and you’ve spent most of today sipping on Soylent, hoverboarding, and relaxing on a virtual beach in between your cybernetic implant appointments. Robots have taken over just about everything—including closing seven-figure deals—so there’s really not much for you to do besides put on your yellow-tinted glasses and count your Dogecoin.

Okay, we admit this is a ridiculous prediction, but there are some folks who really do believe that machines will take over sales in the not-so-distant future. If products can sell themselves using a self-serve model, why involve an actual, human salesperson?

Because people want human-to-human connection, that’s why. Not even a dancing robot can replicate that.

This topic came up during a recent episode of the OV BUILD podcast when host Blake Bartlett asked Leandra Fishman, Twilio’s former VP of Commercial Sales, her thoughts on the trajectory of software sales.

“It’s been amazing to see the product led growth in companies over the last 10 years. I think it’s going to continue to be very strong,” Leandra said. “But I don’t think it’s ever going to replace human-to-human decision-making or information or exchanges. We’re never going to do a very expensive, complex, detailed sales negotiation strictly through a self-serve or a product-led process, but I think it’s going to be just as important.”

Related read: What is product led growth?

Blake noted that a common misconception about product led growth (PLG) is that it’s anti-sales, or that being product-led means you expect customers to someday buy seven-figure contracts without ever talking to anybody. That’s just not going to happen.

“People want to have that human-to-human connection. They want to make sure that questions are answered. So the key differentiation is, well, what is the starting point of that journey that ultimately lands on or results in that human-to-human connection? ” explained Blake. “And I think that’s where the opportunity is. Does the beginning point of the journey start with kicking the tires yourself and using the product yourself and building the trust with the product yourself? I think that we’ll see a lot more of that, but there will always be this huge and extremely valuable, extremely important role of salespeople—especially as those deal sizes and the complexity gets larger as the user continues with their journey.”

Blake and Leandra had a whole lot more to say about the future of software sales, the trick to marrying sales and self-serve, and the key differences between enterprise sales and product-led sales models. Listen to the entire conversation below, and then subscribe so you never miss an episode.

Where to find more episodes of the OV BUILD podcast

Subscribe on Apple Podcasts, Spotify or listen on our website.

Kristin Hillery
Kristin Hillery
Managing Editor
OpenView

Kristin joined OpenView after spending over four years at InVision managing their Inside Design publication and helping build brand love as chief storyteller, lead producer and editor. Before InVision, she co-founded the digital strategy agency Four Kitchens, spent several years in the restaurant industry as a chef, and was Editor-in-Chief of the nation’s largest college humor publication, the Texas Travesty, as an undergrad at the University of Texas at Austin.
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