1:1 Sales Coaching from a 3x Startup VP Sales
You don’t need a manager tracking your activity. You need an expert with you in your deals.
Big-company playbooks fail at startups. An ex-rep from a big brand teaching you how they sold a household name won’t help. I spent 17 years unlocking how to scale sales at VC-backed SaaS and AI startups. Now, I coach mid-market and enterprise AEs on the exact strategies it takes to actually win at startup sales.
“After a quarter of lackluster performance, I knew I needed a coach. I had been chasing deals that didn’t have a real chance at closing instead of the ones that would actually help me hit my number. Since working with Dustin, my quota attainment went from 80% last quarter to 238% this quarter, and I still have the pipeline to do it again. Huge transformation.”
Jesse Taylor · Enterprise Account Executive
The Make Money Model
With Startup Sales Coaching
1 You stop wasting time on deals that won’t close
In the first two weeks we grade every deal in your pipeline together. You’ll see immediately which ones are real and which are dead.
Most reps hold onto dead deals for months because killing them feels like failure. It isn’t. Every hour you take back from a ghost deal is an hour you put into one that pays.
By honing your Closer’s Radar, you get faster at disqualifying, get hours back each week, and fill your pipeline with deals you can actually close.
2 You get a repeatable way to run every deal
No more demo and hope it closes. You’ll run each deal through a clear, step-by-step process that tells you exactly what to do next to get a signed contract.
You’ll know the next step on every deal, who has to do what, and by when. No more guessing, and no more deals stalling out after a good demo because nobody agreed on what happens next.
That way you walk into your forecast meeting knowing your number instead of hoping for it.
3 You get someone in your corner who isn’t your boss
Your manager can fire you. You can’t be fully honest with them, and they can’t really help you anyway. So you’re on an island.
As your coach, I’m not in your management chain. My only interest is helping you win. You get someone you can tell the truth to, who’s been in your seat, and who knows how to fix what’s actually stuck.
We meet every week. You bring your real deals and your real doubts. I help you see what you’re too close to see, and hold you to the standard you set for yourself. That feedback loop is how the skill gets built.
Coaching Strategy
Get on Track and Stay There
We don’t waste time on generic sales theories. We look at your specific territory, identify your pipeline leaks, and build an execution plan designed to get you to the top of your company’s leaderboard.
I wasn’t a natural at sales when I started. I struggled, missed numbers, and had to deconstruct selling down to first principles to survive. When it clicked, I became the top producer at my company. I went on to spend years as a Director and VP of Sales at early-stage startups, training hundreds of reps along the way.
I specialize in one thing: helping net-new B2B technology sellers at early-stage, VC-backed companies close more mid-market and enterprise deals.
If you know that you should be making more money and are tired of deals you’re counting on slipping or ghosting you. If you missed your number, your leads have dried up, your calendar is empty, and your manager is breathing down your neck for a forecast.
If you dream about being the top rep at your company. But no matter what you’ve tried, it’s not enough.
Honestly, it isn’t your fault.
The thing holding you back is not effort or experience. It’s that no one taught you the one skill top reps use without thinking. It’s the difference between a PIP and President’s Club.
I’ll teach it to you.
Ready to Stop Guessing How You’ll Hit Your Number?
Becoming the top salesperson at your company starts with a diagnostic call. Pick a time below and let’s talk.
“I went from not knowing what an objection was to beating my quota every quarter.”
Justin Driffill · Account Executive