The follow-up strategy that won Stitch Fix

It was 2017, the eve of a billion-dollar IPO from a (mostly) bootstrapped DTC company: Stitch Fix.

Earlier in the year, they had become a client of Ampush. Their COO, Julie Bornstein, who is one of my favorite leaders, was speaking to our team.

I had a cool program where every Friday, an inspiring leader would address the team.

After her awesome talk, there was a Q&A. A young, fresh analyst blurted out, “Why did you choose Ampush as your marketing partner?”

Some nervous laughter ensued.

“Well,” she said. “There were three reasons. One, you guys came strongly recommended by several people we trust. Two, your pitch was the deepest and most thorough we saw. Three, your CEO, Jesse, is… pleasantly persistent.”

The team loved that. But the following week, someone asked me, “What does that mean, Jesse? How do you follow up and be persistent to the point where it’s endearing?!”

Here are my Dos and Don’ts.

(PSA: This isn’t for cold email. It’s for after you’ve had an engagement and then someone ghosts.)

If this one sounds obvious to you, that’s good. Because most people do NOT do it.

They send one email and, if they don’t get a response, they drop it. They will get in their head, worry that the person doesn’t like them and make up a million stories.

My rule is: no response isn’t a no… it’s an “I’m busy/this isn’t a priority.”

I send one email a week for three to four weeks and then I switch it to once a month. But legit, I never stop following up.

I’m good with a couple of emails that say, “Just checking in.” You’d be amazed, by the way, at how often the first follow-up gets someone to respond.

That’s because following up shows you are serious.

But if someone still isn’t responding, they are signaling that you haven’t added enough value. Another quick check-in won’t work.

Instead, ask yourself how you can add value to that person. It might be a specific analysis or piece of information.

Maybe there’s a new trend that impacts them and you can go deep. Or, maybe, just a great dinner reservation! But do something that adds value.

If you’ve sent three emails with no response, try LinkedIn. I LOVE texting, if I can — it’s more personal and casual. But it’s totally fine to try multiple channels.

One to three sentences. ‘Nuff said.

Either with reminders in Superhuman/Gmail or on a calendar. Otherwise, you’ll forget.

Ask for a meeting, a review of a document, a signature. Whatever it is, be concise and specific.

Get creative. Sometimes a GIF might elicit a response. Sometimes a silly question. What do you have to lose?!

Never, never, never. I don’t care if you spent hours with the person at dinner and did tons of work. No one owes you anything. Keep it kind, pleasant and helpful.

Unless it’s obvious why you are doing it, like there’s some deadline.

This is the top killer of follow-ups. People worry they’ll be judged. They don’t want to seem desperate. Or they think the person hates them. Usually none of these are true!

You aren’t doing anything wrong. Keep it upbeat, positive and pleasant. You’re trying to be helpful!

It’s okay to go from weekly to monthly to quarterly. But keep the follow-up going. Some of my biggest deals came six months after the initial conversation and lots of ghosting.

So there you have it! Here’s one last bonus of being pleasantly persistent…

It creates a follow-up and follow-through culture internally. Everyone knew that I would circle back on my asks and check back, so people got their work done on time.

Even better, everyone started following up on their own requests internally and externally. This helped us get more work done and improved accountability.

It’s also why I love “inbox zero.”

Once you do this, you’ll never go back!

jesse