Pre-Confession
Culture is what happens when you're not in the room.
It’s not your mission statement. It’s how people talk in meetings. It’s who gets praised, what gets ignored, and how decisions get made when things are on fire.
This week’s story comes from a founder who hit Series A with momentum — and realized too late that, somewhere along the way, the company they’d built no longer felt like theirs.
Not because it was growing — but because it was rotting.
Company Snapshot
Industry: B2B SaaS (Sales Enablement)
Stage: Series A ($12M raised)
Funding: Backed by Tier 1 VC
Team Size: 36
Founders: 2 co-founders
Work Setup: Hybrid (SF HQ + remote)
The Confession
What happened
We raised our Series A in January. Strong numbers, clean metrics. Hired fast. Promoted fast. Everyone told us we were crushing it.
But by July, I didn’t recognize the company anymore.
I was in the office one day when I overheard two new PMs talking in the kitchen.
“If you push back on [CTO’s name], he’ll just shut it down. Better to say yes and quietly ignore it.”
That shook me.
I wasn’t proud of our product velocity. Or our culture. Or honestly, myself.
We were shipping features no one used. People were politicking. Everyone was afraid to speak up.
It felt like the place I used to work — the one I left to start this.
When did it start?
In hindsight? Right after the raise.
We hired 15 people in 60 days. We brought in “adults” — seasoned execs from bigger companies. Everyone had opinions, priorities, frameworks.
Suddenly I was in back-to-back meetings debating OKRs instead of sitting with customers.
And we started posturing. Every conversation was about what would look good on our next board update.
We stopped building for our users. We started building for our investors.
What were the red flags?
We had a senior engineer quit. Quietly. No drama. Just a short Slack message and a polite goodbye.
He was one of our best.
I called him that night and asked why.
He said:
“It just doesn’t feel like I matter here anymore. Everything feels top-down. No one’s asking why we’re building what we’re building.”
That one stuck.
So did another moment — I was 1:1 with our Head of People, asking why our latest hire seemed so disengaged. She said:
“Honestly, a lot of the team is. They don’t feel safe giving feedback. They feel like there’s a ‘right answer’ in every meeting.”
And I realized: I’d become the person with the “right answer.”
What did you do?
I canceled the offsite.
We were planning a Q3 “vision reset.” It was all slides and storytelling.
Instead, I asked every department head to meet with 5 people — ICs only — and just listen. No agendas. No notes. Just conversations.
We compiled every bit of feedback and shared it anonymously at all-hands.
Some of it was brutal.
“No one here knows what we’re building anymore.”
“Everything is reactive.”
“I used to feel proud working here. Now I feel like I’m behind.”
We shared our own reflections too. No defensiveness. No PR spin. Just: Here’s what we got wrong. Here’s how we’ll earn back trust.
Then we started making changes.
We flattened the org.
We sunsetted 3 features that added complexity but no usage.
We brought product and support back into the same Slack channel.
I personally started doing bi-weekly office hours — optional, open, unstructured.
What changed?
The mood shifted.
Slowly, but noticeably.
People started joking in Slack again. PMs pushed back. Engineers challenged roadmaps.
A junior designer told me after a meeting:
“It’s the first time I’ve spoken up like that here. Thanks for making space.”
We’re not “back” yet.
But I’m no longer ashamed of the culture.
We’re rebuilding it — on purpose this time.
What would you tell another founder?
Culture is fragile.
It doesn’t shatter overnight. It frays.
And once it starts slipping, every day you delay is compounding damage.
If people aren’t talking in meetings, if your best ICs are disengaging, if you feel like you’re performing “founder” more than being one — something’s already off.
Pause. Get honest. And fix it before it calcifies.
Final Thought
You don’t lose your culture all at once. You lose it one quiet resignation at a time.
💬 Quick Gut Check – Did This One Hit?
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