Founder-led sales is hardcore: lessons learned

Building a startup is a lot of work, most of the time you’re getting rejected: a VC, a customer prospect, your friends…

I’ve had my fair share of face-plants - but on the sales side of things it’s where it hurts the most:

ICP and Qualified Leads

First off, I learned the hard way that not all “leads” are created equal.

I was so eager to get my product in front of anyone - I spent hundreds of dollars and hours to create “automated drip campaigns” on LinkedIn, Quora, Reddit etc etc.

I chased leads who simply didn’t have the problem I was solving. Think about it like selling coats to penguins.
Create your ICP. Qualify, qualify, qualify. Don’t spend money blindly on tools and platforms and campaigns that lead to nothing.

Segments

Sometimes, you did the homework but even if a person seems the right ICP, they might be in the wrong segment.
Early on, I didn’t think about “business size”. Big mistake. Learned the hard way that sales cycles at Startups vs Fortune 500 companies last and feel very very different.

Timing

Timing is everything. Sometimes you contact people too early in their discovery journey, i.e. they know they have a problem but don’t have a clear path on how to solve it. Other times, you talk to people that just decided to pay for a competitor’s solution.
Fuck. Unlucky.

Messaging

Another pain in the butt of reaching out is that crafting a compelling email is an art.

English is not even my main language (it’s actually Python xd) so I bombed countless campaigns because my messaging was unclear and confusing.

Even with clear messaging, my emails often failed to demonstrate the ROI: I was so focused on what my product did that I forgot to explain why it mattered to them: why it will save them money and time.

In my previous startup I rectified this by creating charts like this - our goal was to show how using our software would lead to a decrease in the amount spent on tickets

Deliverability

The worst part of it all? The EMAIL MAFIA.
Sometimes, the problem is not in what you write, but who delivers it. Spam folder, untrustworthy senders etc etc will hurt your work.

Be THAT guy - follow ups

Finally, being “THAT GUY” aka doing follow ups. Many times, a “no” was really a “not now” or “I’m busy.” Lesson: Don’t be afraid to follow up. A polite nudge can make all the difference.

The hardest setting

All in all, there’s a lot you can learn by doing sales outreach - it’s a nightmare and I hope you also will go through this nightmare and get out of it as a more experienced founder, because it’s a life-defining experience for sure.