Wesley Ross

Building Get Automated Feature Announcements

| Ex - Product Leader @ B2B SaaS

[Wesley Ross @WesleyRoss]

@marckohlbrugge @Hetzner_Online Been putting of the some migration for a while 10+ apps… 😅

[Wesley Ross @WesleyRoss]

Founder-led marketing sounds good on paper.

In practice it often means: ship all day, open laptop again at night, try to explain the release without sounding tired or generic.

That’s part of why updates slip. It’s not laziness. It’s context switching.

Writing a good announcement requires a different brain than shipping the feature. You have to zoom out. Package the story. Pick the angle. Choose the channel.

That extra layer is exactly where a lot of good intent dies.

I’ve felt that pain enough times that I finally started building around it.

That workflow is exactly what pushed me toward building UpdateBerry. com.

The manual version works. It just doesn’t scale well when you ship often.

[Wesley Ross @WesleyRoss]

Jackie Bavaro spent 8 years at Asana, going from first PM to head of product. Her biggest early mistake?

She thought being a good PM meant saying no to everyone.

Here's the framework that fixed it.

[Wesley Ross @WesleyRoss]

Got the domain renewal notice for my side project. I'm letting it expire.

162 commits. Image vision analysis. Stripe billing.
A fully working AI real estate platform.

Zero meaningful traffic.

The funny part? I did validate.

Cold emailed 900 real estate agents.

I validated interest, not willingness to pay. People said "sounds cool!" but nobody was reaching for their wallet.

I took encouragement as validation.

I should have presold. "Here's $29, build me this" is validation.

By the time the product was "ready," I'd spent weeks building features for an audience that wasn't waiting. The code was excellent. The market wasn't there.

So here's my real takeaway: sell before you build.

Get money on the table first. Let paying customers tell you what to build.

Everything else is just a very expensive hobby.

Domain expires in a few weeks. I'm letting it go.

On to the next one.

[Wesley Ross @WesleyRoss]

@Shpigford 😂

[Wesley Ross @WesleyRoss]

Founder-led marketing sounds good on paper.

In practice it often means: ship all day, open laptop again at night, try to explain the release without sounding tired or generic.

That’s part of why updates slip. It’s not laziness. It’s context switching.

Writing a good announcement requires a different brain than shipping the feature. You have to zoom out. Package the story. Pick the angle. Choose the channel.

That extra layer is exactly where a lot of good intent dies.

I’ve felt that pain enough times that I finally started building around it.

That workflow is exactly what pushed me toward building UpdateBerry. com.

The manual version works. It just doesn’t scale well when you ship often.

[Wesley Ross @WesleyRoss]

Senior PM at top companies pays as much as a doctor or lawyer. You don't need management to make real money. Check https://t.co/u1FMQZkMoI if you don't believe it.

Want more practical tactics from operators who've shipped? Follow @wesleyross.

What's the worst career advice you've received from someone who's never built anything?

[Wesley Ross @WesleyRoss]

Jackie Bavaro spent 8 years at Asana, going from first PM to head of product. Her biggest early mistake?

She thought being a good PM meant saying no to everyone.

Here's the framework that fixed it.

[Wesley Ross @WesleyRoss]

Repeated disagreements over features = missing strategy.

If you keep fighting the same battle with engineering or design, stop debating the feature. Write down the strategic principle you actually disagree on. Solve it there.

[Wesley Ross @WesleyRoss]

Sopot, Poland

My favorite place

[Wesley Ross @WesleyRoss]

Here are some mistakes I’ve made (and seen others make) with release announcements:

- Announcing too much at once → user overload
- Focusing on “what we built” instead of “what you gain”
- Posting only once in one channel and expecting adoption
- Waiting too long after shipping (momentum dies)

Quick fixes:

- Limit to 3–5 key stories per update.
- Lead every item with the user outcome.
- Plan multi-channel from the start (social + email + in-app).
- Announce within 48 hours while excitement is fresh.

Another big one: Ignoring tone consistency across channels.

Fixing these has noticeably improved how users respond to new features.

Many of these lessons are feeding directly into the design of UpdateBerry.

If any of these mistakes ring true, reply with your war stories → updateberry. com

[Wesley Ross @WesleyRoss]

@michalmalewicz Living permanently, moved from the U.S to PL couple of years ago.

If you're at InfoShare the next 2 days, lets meetup

[Wesley Ross @WesleyRoss]

Chu's advice: even if you throw it away, write it. Your team deserves that level of clarity.

Follow @wesleyross for more operator lessons from practitioners.

What's one idea you've been meaning to write about but haven't started?

[Wesley Ross @WesleyRoss]

Brandon Chu's writing accelerated his career "probably a decade."

Here's the exact approach he used—and why most people get it backwards:

[Wesley Ross @WesleyRoss]

You don't need viral reach to make this worth it.

The act of writing creates clarity in YOUR mind. That alone compounds across every conversation, decision, and pitch you make.

Viral distribution is a bonus, not the goal.