The Distill - Suck It Up & Sell

Greeting Pioneers,

intros are back in a real way. My daughter has blessed my return to the office and more importantly the writing of intros.

One take this week. No one is going to sell your company better, harder, or faster than you. So saddle up and sell. Not only does it put food on the plate, talking to customers sharpens your product, refines your messaging and sets the stage marketing.

Eat the frog.

Founder-Led Sales: Do It Yourself or Die Trying

We have a new product at Swell. The buyers are different than the users, which means the messaging is more complicated than it once was. I don’t know which of the now many problems we solve is the most painful to our buyers yet, so I need to find out.

All this to say I'm back to cold outreach, in-person visits, and figuring out what makes people say yes. Again.

If you're here too and thinking about hiring a sales rep to skip this part - I don't think you should. Here's why.

Why Founders Hate Sales (And Should Do It Anyway)

Sales is most of our least favorite part. We’re innovators. You didn't start a company to get rejected 47 times by people who don’t really “get” your idea. You didn't quit your job to show up at offices with donuts hoping someone will give you 15 minutes.

You built a product, and now you want to build more product. Sales feels like a distraction from the real work.

Me too. Except sales is the real work.

Why We Can't Skip This Part

Your messaging that gets people to take the leap isn't sitting in a Google Doc waiting to be discovered.

Startups are usually innovating on a few fronts at once - new technology, new market, new business model, sometimes all three. Which means explaining your product doesn't start with a clean one-minute pitch that works out of the gate.

Figuring out the messaging is a craft developed over 100 attempted sales. You'll try positioning it as a cost-saver and watch eyes glaze over. You'll pivot to time-saver and get questions. You'll accidentally describe it as "like X but for Y" and someone will finally say "oh, I get it."

Those 100 conversations teach you which words land, which objections kill deals, and which features the buyer may not care about even when they may be the most valuable to your end user. A sales hire can't do this work for you. They need a script that already works. You have to write it first.

Further, no sales hire will care as much or learn as fast as you will. And critically: you have the unique ability to repackage, reprice, or promise features during the call to make them more likely to say yes.

Nothing Beats In-Person Outbound When You're First Getting Started

For those of you who want to hire a sales rep because you don't know where to start, don't understand optimizing CTR, or feel overwhelmed by funnels and conversion metrics - you're overcomplicating the process. Optimizing is for phase 2. You're in phase 1.

Phase 1 is simple: talk to people until someone buys. Go in-person to the organizations you want to sell to (bearing gifts to get in the door) and talk your way past the gatekeeper.

Show up. Make them like you. Learn what they care about. Always book your next conversation before you leave your current one.

Every step ends with you understanding more of their motivators + a date on the calendar. The second you walk away without the next meeting locked, you've lost control and you're waiting on them. Don't wait on them.

When You're Ready to Hire Your First Sales Rep

You're ready when all of these are true:

• You've closed 10+ customers who actually paid you money and can articulate why they bought

• You have a repeatable pitch that works >50% of the time

• You can onboard a rep in a week because the process is documented

• You're turning down qualified leads because you don't have time

You're not ready when:

• You're just tired of selling and want someone else to do it

• You haven't figured out product-market fit yet

• You can't explain why your last 3 customers bought

If you hire too early, you'll blame the rep when they can't close deals. But the real problem is you never figured out how to sell it yourself. Do the hard thing first. Learn how to sell. Then teach someone else.

Events this week!

Come meet the Sandbox Venture teams at UofL
If you haven't heard, Sandbox is a new program where students build real startups during the semester instead of wasting away in classrooms.

The first cohort had 18 students selected from +100 applicants and several teams are already generating revenue (including Nate Royal and Ethan Havertape leading the pack with DueGooder). It’s a great program, and now they’re recruiting for next year's cohort.

It’s this Thursday, March 19th @ UofL College of Business Atrium at 5:30pm. Register here: https://luma.com/cm2olnnr?tk=dJuVVm

Note’s on The Distill’s co-EICs: Jack Crowdis & Rachel Edenfield

Jack runs the newsletter, helps run KYX. He’s a career startup kid, past founder, and current operator. Weekly contributor. Always editor.

Rachel’s the Founder/CEO of venture-backed Swell, and a driver of KYX. Routinely delivers the city’s sharpest long-form startup advice. Always re-edits Jack’s edits (including this bio).

Know someone who should read this? Forward it, or send them this link.

That’s a wrap 🎬
Keep showing up 👊 
Keep shipping 🚢 
Peace, Pioneers ✌️