Jim Zazenski
Walter Crosby sits down with entrepreneur Jim Zazenski to talk cigars, relationship-driven sales, building a high-end sign business, hiring salespeople, accountability, mentorship, and the lessons learned from decades in business.
What Can a Cigar Shop Teach You About Sales?
Quite a bit.
This episode of Sales & Cigars was recorded at Edward's Pipe & Tobacco in Englewood, Colorado. Jim has been walking through that door for 22 years. His office is one mile away, and by noon most workdays, everyone there knows where he's headed.
The conversation starts with the cigars and the relationships that form around them. For Jim, a cigar shop stopped being a place to smoke a long time ago. It's where friendships get built, business gets discussed, and perspectives get challenged. He calls the regulars he trusts most his informal, unpaid board of directors.
Relationship-driven sales works the same way. The people you'd call for advice are the people who'd take your call.
Inside the Conversation
From the shop, Walter and Jim move into Jim's career: an engineer who became a VP of operations, then a VP of sales and marketing, then the owner of a custom manufacturing sign company. The company specializes in interior signage and wayfinding for large, complex properties, with a client list that runs through Las Vegas.
Jim explains why his company refuses to compete on price. The price is the price. If a customer needs a different number, the conversation turns to value engineering — what changes, what comes out — so quality and margin both survive. He also makes the case that doing the right thing for a customer is worth more than squeezing a single transaction.
Then they get into the realities of managing salespeople:
- Hiring mistakes. Jim tells the story of falling in love with a résumé and a diploma, and what happened when the new hire didn't know how to prospect.
- Compensation plans. Walter's line: a comp plan is a set of instructions. Jim's: salespeople should be the highest-paid people in the organization. Both agree the plan has to point where the business needs to go.
- Account concentration. Jim woke up one day to find more than half his revenue sitting with three clients, and a very comfortable salesperson servicing them. He and Walter unpack whose failure that was and how Jim changed the comp plan without punishing the rep for what he'd earned.
- Autonomy and accountability. Jim gives his salespeople freedom as long as they hit their numbers. Walter's rule is the same, stated harder: you earn your autonomy, and you lose it when the numbers go.
- How a VP of operations put a young engineer on the road with the sales team, and why that kind of hand-off is rarer now.
It's a conversation about cigars, certainly. Underneath it is a discussion about relationships, standards, hard work, and what it takes to build something that lasts.
Key Moments
- 00:00 — Edward's Pipe & Tobacco and 22 years of walking through the same door
- 00:05 — The informal board of directors
- 00:10 — Wayfinding for Las Vegas properties and refusing to sell on price
- 00:17 — From engineer to VP of sales: the mentor who made it happen
- 00:48 — Account concentration, comp plans, and the comfortable salesperson
- 00:57 — The daily cigar: Padrón 5000
- 01:04 — The hire that looked perfect on paper
- 01:15 — Autonomy, accountability, and earning your leash
About Jim Zazenski
Jim Zazenski is an entrepreneur with a background spanning engineering, operations, sales, marketing, and custom manufacturing. His company specializes in high-end interior signage and wayfinding solutions for complex properties, including extensive work throughout Las Vegas.
He is also a longtime cigar enthusiast who has spent more than two decades frequenting Edward's Pipe & Tobacco in Englewood, Colorado.
His daily cigar of choice?
A Padrón 5000.
And his philosophy is equally straightforward:
Life is too short to smoke a bad cigar.
