If I Could Go Back, Here’s What I’d Do Differently​
This week, I want to talk about some key lessons I've learned over the past decade.
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Things I would've done differently in my career if I could go back and do it over again.
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I'm not going to go as far as calling any of these regrets, life is way too short for regrets (especially career ones) but they are learnings that could’ve helped me accelerate my growth, earn more, and enjoy the journey a bit more along the way.

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​1. Think Bigger and Define Success

For years, I treated sales like a survival game. Hit quota. Keep the job. Repeat.
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I didn’t stop to ask the bigger questions: What do I actually want? What does success look like for me?
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For too long, I let others define success for me. Managers, peers, even friends and family.
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It wasn’t until much later that I realized how important it is to define success for yourself. If you don't, you'll struggle to play the long-game and never reach fulfillment or self actualization.
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When I finally started setting goals around what I wanted, not just what was in front of me or what others said I should want, things changed. I started thinking about the bigger picture, got more energy and fulfillment from the roles, companies and deals I was working on and started building the lifestyle I wanted.
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If you haven’t done this yet, take some time this week to write down your own definition of success (I recommend taking yourself out to coffee or lunch with a note pad for brainstorming).
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How much do you want to earn? What kind of life do you want to design around that? Where will you be next year? In 5 years? Then reverse-engineer your career moves to match.
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2. Ask for Help

For a long time, I thought asking for help made me look weak or incompetent.
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So I tried to figure everything out on my own. I wasted hours grinding through problems that could’ve been solved in a 10-minute conversation.

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I remember one RFP early in my career that nearly broke me. I stayed up late for days trying to answer every question myself. I didn’t know enough about the product to do it right and didn’t ask anyone for help... We lost the deal.
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What I didn’t realize then is that sales is a team sport. The best reps I’ve ever worked with aren’t lone wolves. They’re resourceful. They pull in leaders, SCs, marketers, and exec sponsors to strengthen their deals.
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Now I make it a point to ask for help early and often. Whether it’s coaching, deal strategy, or exec alignment, there’s always someone who can help you close faster.

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3. Think Like a Consultant, Not a Rep

This one took a while to figure out and get right.
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Early on, I treated every prospect like they were above me.
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I’d overthink titles, pedigrees, and company names. I’d thank people for “taking the time” to meet with me, like I was lucky to be in the room.
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Then one of my managers said something that stuck: “Exec buyers put their pants on one leg at a time, same as you.”

It seems small, but it really put things into perspective for me.
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When I started approaching conversations as a consultant, someone who helps solve business problems, my tone, confidence, and results all improved. I stopped hard selling and started advising.
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If you sell to marketers, learn about marketing. If you sell into IT, learn their world. The deeper your understanding, the easier it is to speak their language and act like a peer instead of a vendor or sales rep.
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Your time is just as valuable as theirs. When you operate that way, your prospects feel it too.
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​4. Stick It Out a Little Longer

There's been several instances in my career where I walked away too early.
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I left roles and companies only to find out deals I was working on closed and paid big commissions to the person who inherited the account when I left.

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In one case, I moved on from a hot company and decided not to vest my equity... A year later they went public. Had I stuck it out one more year, I would have made well over $100k from my options 😢. A very expensive lesson...
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Looking back, I wish I’d been more patient and stuck things out a bit longer. The grass isn't always greener and in the moment, it can feel like you're in a pressure cooker. If you can dig your heels in and stick it out a bit longer, you may be closer than you think.

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​5. Take Better Care of My Health

I let the stress of this profession beat me up for many years (something I'm still working on).
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The anxiety and stress of working in high growth companies, with a target on my back for over a decade has taken a toll on me mentally and physically. I'll spare you all the details...
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Over the past year, I've been on a journey to better manage my stress levels, diet, fitness routine, alcohol consumption and overall mindfulness.

The key for me has been not taking it too seriously. We sell 1's and 0's, we're not saving lives. Don't get me wrong, selling tech is an amazing career opportunity with huge upside, but it's not worth destroying your health over.

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Taking care of your health should be part of your job. Eat well, get 7+ hours of sleep, move your body, manage your alcohol and protect your peace.

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You’ll sell better when you feel better.

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And don't forget to use your PTO!

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​👉 If this one hit home, be sure to forward it to someone who needs to hear it.
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-Jesse

AI Won’t Replace You...

But It Might Replace The Reps Who Aren't Using It.

We’re entering a new era: the rise of the Super Rep.
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AI isn’t here to replace sellers. It’s here to supercharge the ones who know how to use it.
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A Super Rep leverages AI to work 10x more effectively than the average seller, closing more deals, faster, with fewer wasted cycles. The teams that figure this out will be the ones that win.

The problem?
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Most sales AI tools miss the mark. They’re focused on the wrong workflows, buried in clunky platforms, or just rebranded “AI SDRs” that buyers learn to ignore. Sales Players don’t need another confusing platform. What we need is AI that actually takes admin work off our plates and frees us up to sell.

That’s where ChatAE comes in. Always-on AI agents that give you account intel and targeted messaging in minutes, customized to your role and team. ChatAE doesn’t just save you time, it creates Super Reps. And Super Reps win.

Get ChatAE

Featured Episode: 7 Tips for Getting the Most Out of Your Meeting Recording Tool

Some tips for getting the most out of your sales meeting recordings tool (Gong, Chorus, Fathom etc.)

Listen to the Episode

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