Stephen Defina joined me on the Conquer Local podcast to share how finding a sales mentor who bets on you can completely change the trajectory of a sales career.
Every seller I know can name two or three people who changed the trajectory of their career. Stephen Defina talks about mentors like that, and after spending 20 minutes with him on the Conquer Local Podcast, I understand why so many sellers point to him as one of theirs. Steve is VP of Revenue at Clearbanc and one of the most respected sales leaders working in the Toronto tech ecosystem.
Steve grew up in Connecticut, went to business school there, started his sales career in New York, and then relocated to Toronto where he has been for nearly nine years. He cut his teeth at a startup called Yodle, where the sales team scaled from 35 to more than 300 people during his run. That kind of hyper-growth environment teaches you things you cannot learn in a classroom.
Throwing Bets on the Table
One of my favorite moments was Steve telling a story about a rep on his team who insisted that the scripted pitch would not work in Mandarin. Most managers would have shut that down. Steve made a deal with her. Do it ten times. If nobody buys, we burn the script. Or write one better yourself.
It worked. To this day they have an inside joke about nobody in Mandarin buying when you read a script to them. The deeper lesson was this:
“You have to figure out how to read your audience and how to earn credibility. As a leader, you cannot be afraid to throw those bets on the table to earn the respect of your team so that you can show them what is possible.”
That is what good mentorship looks like. Not protecting your own rightness. Betting on the rep’s instinct and giving them the room to prove it.
Why Communities Like Revenue Collective Matter
Steve is deeply involved in the Revenue Collective (now Pavilion). He walked me through why communities like this matter for rising sales leaders.
His point was that nearly 4,000 global members share unfiltered information that you simply cannot get from conferences, blogs, or your own boss. The introduction of associate membership, designed for up-and-coming leaders aspiring to be first-time VPs, is the thing he wishes he had when he was coming up himself.
If you are an individual contributor on track for leadership, or a first-time manager trying to find your footing, a peer community is one of the highest-ROI investments you can make. For more on how I think about community and personal growth, see my post on Jeffrey Hayzlett on building a strong C-Suite community.
Humility Is the Common Thread
Steve pointed out something I noticed too. The most impressive leaders in Revenue Collective tend to be the most humble. You sit down for coffee expecting a polished executive and you end up with someone asking you as many questions as you are asking them. That pattern repeats itself across the best sales leaders I know.
Humility in a leader is not weakness. It is the behavior that creates the conditions for learning across the entire team.
MANS: The Acronym Every Seller Should Know
Steve shared one of my favorite acronyms of the year. MANS stands for Mutually Agreed Next Step. It sounds simple. It is transformational in longer sales cycles.
At every point of qualifying, you end the conversation with a mutually agreed next step. “If this person needs to schedule another call, is there anything you need to see or a reason we would not be able to move forward?” That kind of explicit alignment kills the ambiguous pipeline that plagues enterprise deals.
- Agree on the next step at every stage
- Name the concerns that could derail the deal
- Document the agreement so both sides are accountable
- Protect yourself from the deal stalling out quietly
For more on how I teach rigorous pipeline hygiene, see my piece on how I teach sales reps to master prospecting.
What I Took Away From Steve
- Bet on your reps in public. It earns trust and builds new playbooks.
- Peer communities accelerate leadership growth faster than any course
- Humility is a differentiator among the best leaders
- Run MANS at every stage and your pipeline gets honest fast
Stephen Defina is the kind of mentor every seller should hope to work for at some point. If you are in Toronto tech and have not crossed paths with Steve yet, you will.
Who is your current mentor, and what is the last thing they bet on for you?