Mavens of Modern Sales – Jonathan Coleman
Welcome to Mavens of Modern Sales, where we take a deep dive with the sales leaders pulling sales teams in the 21st century to get their insights on leadership, strategy, industry trends, and more.
This week we talked to Jonathan Coleman, Head of Sales at First AML.
A lot of people say outbound is “dead,” but you’ve seen it evolve firsthand. What do you think separates teams that are still crushing it from those that are struggling?
Outbound isn’t dead – it’s just evolved, and that’s a good thing. Tools like Outreach and Apollo.io have tricked teams into treating sales as a volume game, but it has always been about quality and relevance. The best teams deeply understand their prospects – how they’re measured, the challenges they face daily, and what truly matters to them. A phrase I love: ‘Speak like you were in the room at their monthly all-hands.’ The teams that master this mindset will continue to be successful.
You’ve moved away from old-school sales tactics like hiding pricing and running never-ending discovery calls. What’s one outdated sales habit you still see all the time, and what should reps be doing instead?
Objection handling just for the sake of it. Sometimes, when I hear some cold-calls, I always pick up when I can and try to be candid. But when I say, ‘We have a hiring freeze until X date (9 months out),’ I often get, ‘OK, let’s book a call next week to plan ahead.’ That’s purely self-serving. Instead, respect the timeline. If a prospect gives you a date, set a follow-up closer to that time – and move on.
You said you’ve learned a lot of hard lessons in sales. If you could go back and give your younger self just one piece of advice, what would it be?
Detach from the outcome – learn to love “running a great process”. This would have saved me a lot of stress and self doubt.
As a Head of Sales, how do you create a culture where reps actually want to ask for feedback and collaborate, instead of trying to figure everything out on their own?
Be vulnerable. That’s it. Share your losses, make it OK to discuss mistakes, and celebrate learning moments. When leaders openly admit challenges, it creates psychological safety for reps to do the same. Reinforce this with structured feedback sessions and peer coaching – all of this starts at the top.
Buyers have changed a lot over the past few years. What’s the biggest shift you’ve noticed, and how should sales teams adjust to keep up?
More people in the picture. This essentially means there’s now a lot of conversations that need to take place outside of the sales reps view. Sellers need to learn to equip their prospects for these internal discussions.
Is there a book, tool, or resource that’s had a big impact on how you approach sales and leadership, something you think every seller should check out?
Two books – The Qualified Sales Leader by John McMahon which provides a masterclass on building and leading high-performing sales teams, and The Respected Salesperson by Arishma Singh – which has an amazing tool kit for sales people and is a must-read for any seller serious about growth.
What’s one leadership lesson that took you a while to learn, but completely changed how you manage and develop your team?
You have to let people get to the answer on their own. Telling people what to do is actually training them to rely on you for the answer – guiding them to get there on their own teaches them to think critically (and will eventually start to get there without you).
