Nobody on the team that built Smoke Cartel had the job title they ended up needing. Including me.
I spent the company's first four years as Operations Manager before I ever held the CEO title. My co-founder started as CEO and moved into President and CTO. Neither of us was formally trained for the jobs we grew into. Before any of that, I ran a cottage business building decorative terrariums, handling production, sales, and customer education all by myself. Nobody handed me that job title either.
So at some point I stopped expecting the perfect title on anyone else's resume. Here's what I look for instead.
Hire for the trait you can't teach
Skills can be trained. Willingness to learn mostly can't. A lot of my best hires didn't look great on paper: they were brand new to the field, or they didn't have the "proper" degree for the role.
I've worked with incredible people who had master's degrees. I've worked with incredible people who never finished their GED. A degree measures one type of intelligence, and the best teams aren't one profile cloned a thousand times.
If you want a filter, skip the degree requirement and ask for a well-written cover letter. Every one of my best hires could explain, on paper, why they wanted the job and how they'd actually help the company.
The guy who'd never held a bong
One of my best hires opened his cover letter by telling me he wasn't the applicant I was probably looking for. Then he told me he was the applicant I actually needed.
He'd never tried a cannabis product and never wanted to. "My son would be a better fit culture-wise," he wrote. "I've never even held a bong." But he loved our company ethos (and that we let people bring their dogs to work), he'd watched our growth, and he knew he had exactly the skills to get us to the next level. Thirty years of them.
He didn't need to love the product to be great at the job. He was already great at the job. He just wanted to do it somewhere that actually wanted him.
The programmer I almost talked myself out of
Our first dedicated programming hire took about a year and a half to find. We needed someone who knew about five programming languages and could pick up three more, including the one Shopify runs on. My co-founder had one non-negotiable, advice he'd carried from his own mentor: no formal computer science training.
Months of cold outreach, paid ads, and outright poaching attempts got us nothing close. Then a resume showed up that hit about half the boxes. The critical languages were there, and if she was willing to learn, I believed she could pick up the rest.
I almost passed anyway. She was a social activist in a field that had nothing to do with ours, and I let myself worry that might conflict with the job. (It didn't. What someone cares about outside of work has nothing to do with whether they can do the work.) She was also still in college, and I wanted someone who could commit full time.
But I'd gone six months without even landing an interview, so I brought her in and told her straight up I was worried about her output as a student. She didn't argue. She calmly named the exact gaps she'd need to close to excel in the role. She got the job.
She finished ten weeks of programming training in eight. She built our internal team-management software from scratch. She ran the cables and set up the servers for every office move we made. When we got hit with a Slowloris attack, she and my co-founder were the two people in the server room rebuilding everything by hand, all day and all night. She also brought in our best social media manager, a fresh college recruit who grew into our brand manager and, after the acquisition, ran brand for every e-commerce site the acquiring company owned.
Half the boxes. 😅
You probably can't spot grit in an interview
I never found a reliable way to spot grit ahead of time, and I stopped pretending I could.
One hire struggled so hard early on that I seriously considered letting her go before she'd even finished ramping up. She became one of the most integral people on the team, the kind of person you build a department around a few years later. Another was obviously the right fit from the first real conversation. I never found the tell that would have told me which one I was looking at.
What actually worked was giving people enough runway to prove it either way.
How to actually hire for this
- Audit your job posts first. Look for language that quietly genders a role or reads narrower than the job really is. You lose scrappers before they ever apply.
- Train your hiring team to spot a trainable mindset, not to gate on a technical background most of your best people didn't have either.
- Ask every candidate the same questions. Different questions for every applicant means you're hiring on personality, not skill. Have your best current people answer them too, so you have a real bar instead of a vibe.
- Ask for a cover letter. It tells you more than a degree line ever will.
- Give runway. Your day-one read of someone is a guess, not a verdict.
- Show people what's possible. When you're teaching a skill to someone who's never been told it was available to them, bring in outside voices who've done the job and don't look like the default image of who does it. People can't picture a future they've never seen modeled.
Want the book when it's ready?
This post is adapted from a chapter of The Team You Build, the book I'm writing about building a team that will outlast you. Drop your email below and I'll let you know when it's out, along with new posts on hiring, operations, and running a business that doesn't depend on you holding it all together.
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