Pre-Confession

At eight people you do not need an executive. You need a builder who still touches the work. Even with great hires, no one will ever care like the founder. If you stop talking to customers, stop reading support, and stop looking at the ad account, the company drifts. The title is not the job.

This is a story from a seed stage founder who slipped into big company habits and had to claw back to the trenches.

Company Snapshot

  • Industry: B2B SaaS for workflow analytics

  • Stage: Seed

  • Funding: 1.4M raised

  • Team Size: 8

  • Founders: Solo

  • Work Setup: Remote with a monthly on site day

The Confession

What happened

Somewhere after hire number six I started performing the role instead of doing the job.

I stopped joining customer calls because we brought in a success lead. I stopped reading the support queue because we set up a rota. I stopped checking the ad account because our growth person had a plan. I skimmed product docs and told myself I was staying out of the way.

My calendar filled with manager things. Forecast reviews. OKR syncs. Board prep. I wrote long updates and said phrases like strategic alignment and go to market motion. People nodded. I nodded back. Then I logged off and felt weirdly empty.

The product kept moving, but the edges got fuzzy. We shipped features that sounded smart in meetings and landed flat in the wild. The copy lost the bite it had when it came straight from user calls. Ads spent money but did not echo how customers talk. Support replies took longer because the team did not have the fast context I used to bring.

By the end of that second month the numbers looked fine at the top and off at the bottom. Demos booked were up. Trial starts were flat. Activation slipped from thirty one percent to twenty six. NPS comments shifted from short and warm to long and polite. Churn ticked from two point one percent to three point eight. No single fire. Just a colder room.

Why did it happen?

I wanted to play big time CEO. I wanted to look like the people in my feed. Every morning LinkedIn told me that real leaders delegate, hire fast, step out of the weeds, and focus on vision. I scrolled past victory laps and headcount announcements and photos from offsites. I started treating the company like a stage. I practiced the role and slowly stopped doing the job.

I told myself that letting go was leadership. In reality I was trying to keep up with a story that was not ours yet. We were eight people. We still needed fingerprints on the product, in support, inside the ad account, and inside the docs. Even with strong hires, no one will ever care like the founder. That is not a criticism of the team. It is a fact of ownership.

I also liked how the performance felt. Writing updates. Talking strategy. Sitting in planning meetings. It felt important. It also let me avoid the uncomfortable parts of the work where you can be wrong in real time on a call with a frustrated user.

LinkedIn made building look clean. Our reality was not clean. I forgot that the job stays close to the work a lot longer than the outside world suggests.

The Turn

A renewal call cracked it open.

A long time customer said they still used the old builder because the new one felt slower. They asked a simple question about a step in onboarding. I opened the app to show them and got lost three clicks in. I heard myself talking in abstractions. They were quiet. I said I would follow up by end of day and ended the call early.

After that I did a calendar audit. Nineteen days since my last real user conversation. Three weeks since I read a support thread end to end. One quick glance at the ad account in a month. Everything on my calendar was internal.

I did not need another meeting. I needed to log in and do the work.

What did you do next?

I did not swing a hammer at the org chart. I went back to the trenches and let that change me.

Thirty days of trench promises

  • Two live customer conversations every day before lunch

  • One hour reading and answering support

  • Thirty minutes in the ad account and on the landing page with one written note

At five each day I posted a short update in Slack. Who I talked to. What I heard. One change we will make.

Week one was humbling. I had to ask the team to re explain edge cases. I caught myself giving advice before I understood the flow. By week two I heard patterns again. Confusion clustered in the same two onboarding steps. Copy that made sense to us and not to busy humans. An ad group that looked fine on cost but brought thin leads.

Hands on fixes in that same month

  • Rewrote the first five onboarding emails with lines pulled from calls

  • Sat with an engineer and removed two steps from first run, then walked three new users through it on Zoom

  • Paused two ad groups and moved budget to a boring search term that shows high intent

  • Took the top ten support macros and rewrote them in plain language with links to the exact place in app

Change the shape of my job

  • A weekly builder block for three hours that does not move

  • One daily triage window at four for approvals and async replies

  • A simple rule for the team. If a decision touches first run or first value, I am in the room or I write the doc

  • Short founder office hours on Wednesday so people can bring real user context, not just slides

Where are things now?

Six weeks later activation moved from twenty six percent to thirty nine. Churn eased back to two point five. Time to first response in support dropped by forty percent because our macros and help docs now match how people move. The ad account spends less and brings better trials because we stopped chasing clever and started matching intent.

Inside the team the mood changed. Our success lead said the product note felt like the old days again. The growth person asked if I would keep looking at the account with them once a week, not to override, but to translate what users say into what we show. Engineers started posting short Looms of new flows with real voices from calls layered in.

I still run the company. I still do one on ones and board decks. I just measure myself by a different scoreboard. Hours with customers. Time in the product. Words I wrote that shipped.

What would you tell another founder?

Keep this simple and run it every week.

Do a real audit

Count last week. How many live user conversations. How many hours in support. How many times you opened the product and the ad account. Write the numbers and share them with the team.

Set trench minimums

Pick small non negotiables for the week. For example five user conversations, two hours in support, one hour inside the product and the ad account. Hit them before you add new projects.

Own the first value moment

If a choice touches first run or the first win, you are in the room or you write the doc. Delegate later stage work. Guard the front door.

Make the team bring the user, not slides

When someone asks for a decision, require one short quote from a real user and one clear point of view. No opinion piles.

Rewrite one surface every week

A landing page section, a help article, an in app headline, a macro. Use exact phrases you heard from calls. Ship the words you wrote.

Build a small scoreboard

Track four things every Friday. Hours with users. Activation or your lead metric. Time to first response in support. Words you wrote that shipped. If one drops, spend next week in that trench.

Put the feed on a diet

Unfollow win theater for a month. Ten minutes daily cap on social feeds. Spend that time with a customer instead.

Final Thought

Titles are for LinkedIn. Progress comes from conversations.

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