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What Working in a Bicycle Shop Taught Me About B2B SaaS Sales
Why the Best Salespeople Focus on Helping, Not Pitching
Gregory Kennedy
June 23, 2025
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What Working in a Bicycle Shop Taught Me About B2B SaaS Sales
Roadie Extrorinaire!
I was at the bike shop picking up my road bike, chatting with the manager whom I have known for years, and he asked, “Do you want to work here?”
“What? Like on the weekend?”
“Maybe two days a month?”
“Do I get discounts?”
He said yes, yes, and yes.
And that’s how it happened.
Just as Jeff Bezos would require everyone at Amazon, including himself, to undergo an annual customer service refresher, I thought this would be a great opportunity for me to do something similar.
I worked there for about six months before we left California for Seattle, and it was a blast. I got to hang with bike bros, sell bikes to happy kids, and even led the shop ride on Sunday for newbies.
And just as I had hoped, I learned a ton about sales. It was by far the most enjoyable refresher training course I've ever taken, and I even got paid. (But I spent all the cash on discounted bike parts 😢.)
Here are my takeaways on what it takes to be world-class at selling $10,000 bicycles, which is ironically the same price as some small annual SaaS subscriptions.
Build a Rad Team
Everyone was helpful and easy to work with. Some were a lot more knowledgeable and experienced, but they were always happy to lend a hand and help others out.
The lesson: Every great go-to-market organization needs esprit de corps or a true sense of camaraderie, enthusiasm, and devotion in order to crush it.
Top-Notch Leadership Matters
At the store I worked at, the manager had been with the org for a long time, was well respected, and knew everything there was to know about bicycles and store operations.
The lesson: Leadership matters. Great leaders are supportive, inspire the team, and set the tone for how people work together.
Location, Location, Location (Or Distribution, Distribution, Distribution)
They got a lot of foot traffic because of the location, and that helped with walk-ins who occasionally bought stuff. It also made it easy for regulars to drop in to shop.
The Lesson: Marketing and awareness of your brand or product are vital to provide salespeople with a steady stream of able and willing buyers.
Know Your Customer
Over time, I was able to segment customers and even found my niche, which was moms and kids. I must have sold 20+ kids’ bikes because mom isn’t leaving without a bike.
The Lesson: Become proficient not only in qualifying but also in segmenting customers early in the process to direct them to the right product or salesperson.
I Learned to Step Selling
Walking into the store is the SQL of bicycle sales. The test ride is the product demo. When a customer lights up when touching a bike (product), stop talking. Let them experience it. It’s obvious when they find what they are looking for.
The next step was to answer questions succinctly and get them to do a test ride. Most rides ended up in a sale.
The catch was that everyone at the bike store was a complete bike nerd. So we needed to hold back a bit. Sure, customers liked to chat and maybe ask about who we thought might win the Tour de France, but most customers are just looking for something to ride. They are not looking for an in-depth discussion on gear ratios.
This was true at all price points.
We would sell bikes priced between $5,000 and $10,000 all day long. Those people know what they are looking for. Sure, they have questions, but no one drops $10k without doing some research on their own. Usually, a lot of research. And they tend to be pretty knowledgeable, which is not far from most SaaS customers.
But the most important lesson I learned on my first day at the bike shop was: You can only help people buy. You can’t sell to them.
This is really hard for nerds.
Or many tech people.
Or anyone with lots of domain knowledge, like founders.
We live in a society that holds knowledge and being ‘smart’ in great esteem. But no one wants to buy something from a know-it-all. They just want to buy something that will work for them and have a pleasant experience when doing so.
Was I Good at Selling Bikes? Hell Yes!
I hit the weekend leaderboard many times, but my sweet spot was selling so many kids’ bikes that the shop could barely keep them in stock.
The Gregory and Paul Show With Guest Imran Patel Friday, June 20, 2025
On the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is debating this week.
On this episode, we chat with Imran Patel, the PhD‑educated founder and CEO of Syft Data, a Los Angeles‑based startup building AI-powered, no‑code tools to help B2B companies collect and act on high-quality first-party analytics and intent data.
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I'm Gregory Kennedy, former creative director, 3x head of marketing, and founder of Vibe Your SaaS. I help early-stage startups build real momentum with strategic clarity, AI-driven execution, and zero BS.
Oh, and one more thing, I love bicycles.
Greogry Kennedy // Vibe Your SaaS // www.vbmrktr.com