I sat down with Brandon Barton on the Revenue Collective’s Is This a Good Time podcast for a short 15-minute conversation about how I went from working on a farm in Saskatchewan to leading customer-facing teams for a global SaaS company. The format is tight on purpose. Brandon asks simple questions and members give incredible answers. Here is the longer version of mine.
Where Saskatoon Actually Is
Brandon joked that he could finally teach people where Saskatoon is. For the record, it is about six hours north of the US border, where Montana and North Dakota meet. Drive from the border for six hours into Canada, and you will find a city of about 350,000 people surrounded by some of the most productive farmland on the planet.
The Farm Work Comes First
The earliest working lessons I learned came from the farm. Long hours. No shortcuts. The weather does not care about your plans. You show up, you do the work, and you watch everything you built get tested by things beyond your control. That mindset translates almost perfectly into sales.
The Radio Years
I got into media at 16 working at a local radio station. There is no money on the air unless you are Elvis Duran or Ryan Seacrest, so if you wanted to get paid, you had to sell. I was doing play-by-play hockey and selling ads on the same games. One of my customers was a young founder named Brendan King. Nine years later he called me to be the first sales hire at a 20-person startup called Vendasta. That is the story arc.
Building the Sales Guild
At Vendasta I led what we call the Vendasta Sales Guild as Chief Customer Officer. That covered:
- Frontline sales teams
- Account management
- Customer success
- Retention
- Onboarding
The Guild existed because revenue does not come from one function. It comes from the hand-offs between all of them working cleanly. For more on how that structure plays out, see my post on Brendan King on scaling Vendasta, and what makes a great sales team.
What I Look For When Hiring
Brandon asked what kind of talent I was looking for. The honest answer is I look for people the way our chairman taught me to look at companies. Find great people first, figure out where they fit second. The specific roles I was hiring for at the time included:
- Director of training and enablement
- Captains and directors of sales
- Top sales talent across leadership layers
The more senior the hire, the more important the attitude for learning. Titles matter less than the ability to absorb new systems, new tools, and new markets without losing momentum.
Advice I Would Give My Younger Self
A few things I wish I had learned earlier:
- Relationships built during downturns pay off for decades
- Personal brand is a career asset. Start building it before you need it.
- Every technology shift is an opportunity if you adopt early and teach others
- Protect your integrity. It is the only thing nobody else can give you
If you are early in your career and feeling lost, read my post on why investing in yourself is the real turning point.
What I Took Away From This Format
Brandon’s 15-minute format is the exact opposite of the hour-long interview. It forces you to be direct. I recommend subscribing to Revenue Collective and Is This a Good Time if you are anywhere in the revenue function. The shorter form is a great way to pick up one idea you can actually use the next day.
What is the earliest working lesson that still shapes how you operate? I would love to hear about it.