Before leading revenue at Nift and co-founding Mile Square Labs, Preston Junger helped build one of tech’s most iconic sales teams—Yelp. In this episode of Knocking to 10, Preston shares timeless lessons for founders scaling beyond founder-led sales, from building culture that drives performance to embedding grit into your early GTM motion.
Preston Junger helped build one of the most iconic sales cultures in tech—Yelp. Now the VP of Revenue at Nift and co-founder of Mile Square Labs, he’s spent the last decade helping startups go from founder-led selling to scalable sales engines.
In this episode of Knocking to 10, Preston joins us to unpack real lessons founders can use to build world-class go-to-market (GTM) teams without the burn.
There’s a common trope in startup land: “Never hire big company people.” But Preston’s story flips that advice on its head.
After stints at Apple, Yahoo, and IAC, he was recruited by Yelp in 2008—just 80 employees in a scrappy SF office. Despite coming from polished enterprise environments, he thrived. Why?
Key Lesson: Hire for entrepreneurial mindset, not just pedigree. Ask candidates how they’ve solved problems with limited resources, invented workarounds, or pursued goals without clear playbooks.
“The best salespeople don’t wait for direction—they find the levers themselves,” Preston says.
When Preston joined Yelp, SDRs didn’t exist. Cold outreach meant picking up the phone—100+ times per day.
To keep morale high and reps engaged, Yelp invented Yelp University—a gamified onboarding and development program that rewarded hustle, celebrated wins, and built real camaraderie.
Key Takeaway for Founders: If you want your team to run through walls, don’t just manage their output. Build a culture of celebration, growth, and team energy—even if you’re remote.
“If you're building a sales team at a startup, your culture is more important than your product. People have to believe they’re building something that matters.”
Founders love dashboards. But according to Preston, early-stage companies often obsess over the wrong metrics.
Overrated: Call volume
Underrated: Message-market fit, rep resourcefulness, and deal quality
Instead of asking “How many calls did we make?”, ask “What did we learn about this ICP, and how can we do better tomorrow?”
“What matters is who you're targeting, what you're saying, and how fast you're improving. If you're saying the same thing to everyone, you're not learning.”
Preston now helps dozens of startups transition from founder-led sales to repeatable systems via Mile Square Labs.
His process?
“You don’t need a 100-page playbook. You need a real partner who can help you organize, test, and get reps executing consistently.”
The most successful founders stay involved, stay curious, and invest time in developing the people they bring on.
When asked what lesson he’d tattoo on a new VP of Sales, Preston’s answer was simple:
“Don’t forget the people.”
Too many leaders fixate on tools, product, and process—and forget the humans doing the work. Invest in your team. Know what motivates them. Care.
Another one Preston lives by:
“I remind myself often that I don’t know everything. Staying uncomfortable is where the growth happens.”
One of Preston’s earliest sales lessons at Apple? Don’t be a “piker”—someone who does the bare minimum to skate by.
Whether you’re an SDR or a founder, don’t settle for checking the box. Aim to build something great. Invest in people. Build culture. Learn constantly.
Because if there’s one theme that ran through Preston’s career—from Apple to Yelp to startups—it’s this:
“You can’t fake grit. But you can build the environment that inspires it.”
Listen to the full episode on Spotify or Youtube..
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