Rebuilding My Personal Brand at 30 Years In

I spent decades building systems, not a “personal brand.”

For most of my career, my “brand” was:

Do the work.
Make the system stable.
Keep the contracts.
Move on to the next fire.

That worked… until it didn’t.

Repositioning as a fractional CTO / architect forced me to do something I’d mostly ignored:

Treat my own reputation and online presence as a product.

1. Why Rebuild Now?

The catalyst was a combination of:

Positioning pain:
- Hearing:
  - “Healthcare person.”
  - “Developer.”
  - “Not sure how to use you.”
- While I was trying to sell:
  - architecture
  - CTO-level thinking
  - system design
An audit of my own assets:
- Old website: outdated, underwhelming, misaligned.
- LinkedIn: more résumé than positioning.
- No coherent narrative about what I actually do now.
The fractional CTO decision:
- I didn’t want another full-time operator/CEO role.
- I wanted:
  - to apply 30 years of experience across multiple companies
  - to focus on architecture, strategy, and systems

You can’t do that effectively while your public presence still says:

“Random founder who did some healthcare thing.”

2. The Old Brand (If You Can Call It That)

The “before” state looked like:

Website:
- Basic.
- Company-focused, not personal.
- Sparse on:
  - outcomes
  - case studies
  - clear offers
LinkedIn:
- Chronological job history.
- Light on:
  - what I actually do best
  - why someone should hire me now
Overall:
- No intentional story.
- Just “here’s what I’ve done,” not “here’s how I create value.”

I didn’t think about “brand.”
I thought about “delivery.”

3. What Wasn’t Working

Signals something was off:

Calls where:
- people were clearly confused about:
  - my role
  - my lane
  - my strengths
Being slotted as:
- “developer”
- “healthcare guy”
- “implementation help”
- instead of:
  - architecture
  - systems strategy
  - fractional CTO
Lead quality:
- Getting inquiries that didn’t match:
  - my experience level
  - my pricing
  - the kind of problems I solve best

If people keep mis-labeling you, your positioning is wrong, not their eyesight.

4. The Rebuild Process

The website rebuild was its own project:

Discovery
- What am I actually selling?
- Who is the ideal buyer?
- What problems do I solve that justify top-tier rates?
Content work
- Pulling stories out of my own history:
  - $100M flow
  - 99.9% uptime
  - zero contract losses
  - $20M replacement cost
- Turning them into:
  - concrete case studies
  - proof points
  - not self-indulgent nostalgia
Execution
- Platform: something I could control and edit myself (no agency hostage situation).
- Design: clean, readable, clear hierarchy.
- Writing: direct, no fluff, geared to non-technical decision-makers.

Helped by:

External eyes:
- people willing to say:
  - “This isn’t clear.”
  - “You’re underselling this.”
  - “This sounds like generic dev marketing.”

The process was less about pixels and more about forcing clarity.

5. Positioning Shift: Operator → Fractional CTO / Architect

Before:

I sounded like:
- “Former founder who did some healthcare stuff.”

After:

I’m positioning as:
- Fractional CTO / Principal Architect who:
  - designs long-lived systems
  - prevents multi-million dollar rewrites
  - gets platforms out of pilot hell into production

What stayed the same:

The underlying experience:
- Conductor
- state contracts
- architecture decisions

What changed:

The frame:
- From “here’s my backstory”
- To “here’s what you can buy from me right now”

6. Brand Assets Created

During the rebuild I created / assembled:

Website copy:
- Clear offer pages:
  - Fractional CTO
  - Architecture review
  - Rescue/rewrite assessment
Case studies:
- $100M platform
- 20-year uptime story
- $20M replacement cost
- Zero contract losses
Blog / post series:
- These posts you’re reading:
  - packaging experience into:
    - stories
    - lessons
    - evidence
Audit / credibility docs:
- Third-party assessments
- Technical overviews
- System diagrams
Updated LinkedIn:
- Headline aligned with current offer
- About section framing outcomes, not job history

This is all “brand,” even if it doesn’t feel like it.

7. What I Learned About Personal Branding

A few uncomfortable truths:

If you don’t define your story, the market will do it for you.
- And it will get it wrong.
Your best work doesn’t speak for itself.
- It has to be:
  - extracted
  - framed
  - contextualized
- or it just looks like “some job you had once.”
Technical excellence ≠ clear positioning.
- The people who might hire you:
  - don’t read your code
  - don’t live in your infra
- They respond to:
  - clear outcomes
  - relatable risks
  - trust signals
Branding is packaging truth, not faking it.
- The raw material is real.
- The work is organizing it so others can actually see it.

8. Why Write a Meta Post About This?

Because people see:

The polished site
The crisp positioning
The nice case studies

…and assume that:

“You’ve always had this clarity.”

They don’t see:

The years of mis-positioning
The opportunities missed because you looked like “just a dev” or “just a healthcare person”
The grind of writing, rewriting, and digging up evidence

This post is about:

Making the process visible
Showing that repositioning is:
- work
- uncomfortable
- necessary if you want your next 10–20 years to look different than your last 10–20

9. Before vs After

Before:

Identity: Founder/CEO/Healthcare tech guy
Messaging: vague, undersold, too much history, not enough offer
Pricing: constrained by mis-positioning
Inbound: misaligned leads

After:

Identity: Fractional CTO / Architect for long-lived, high-risk platforms
Messaging: outcome-driven, architecture-focused, proof-backed
Pricing: aligns with value of avoiding multi-million dollar mistakes
Inbound: better fit with:
- B2B platforms
- founders with serious systems
- companies scared of rewrites and outages

Not perfect, but dramatically better.

10. Was It Worth It?

Yes.

Could I have kept going with the old “quiet expert” profile?

Sure.
But I’d stay:
- undervalued
- misunderstood
- limited to a narrow band of opportunities

Rebuilding:

Forced clarity about what I actually want to do.
Aligned my story with:
- my skills
- my desired clients
- my desired pricing

If you’re 20–30 years into your career and still leaning on:

“They’ll just see how good I am,”

you’re leaving a lot on the table.

You don’t need to become an influencer.
But you do need to become legible.

That's what this rebuild is really about.

Context → Decision → Outcome → Metric

Context: 30 years of building systems, but public presence screamed "healthcare developer" not "fractional CTO / architect." Leads were misaligned; pricing was constrained by positioning.
Decision: Full rebuild: new website with clear offers, case studies with concrete metrics, blog series packaging experience into evidence, LinkedIn overhaul from résumé to positioning.
Outcome: Leads shifted from "can you code this?" to "can you help us not screw up our architecture?" Conversations start at the right level instead of explaining what I actually do.
Metric: Before: 70% of intro calls were mis-positioned. After: dropped to ~25%. Average engagement size increased 3x. Three fractional CTO engagements closed within six months of repositioning.

Anecdote: The Call That Made Me Rebuild

In 2022, I got on a call with a founder who'd been referred by someone who knew my work. Great intro. Warm lead. I was excited.

Ten minutes in, I realized he thought I was a senior developer he could hire to code features. Not an architect. Not a CTO. A hands-on coder.

I tried to explain: "I've been building and running platforms for 20 years. I can help you think through your architecture, your team structure, your technical strategy..."

He cut me off: "Yeah, but can you write React?"

That was the moment I realized my positioning was broken. The referral knew my value. But by the time it passed through my website and LinkedIn, it had been filtered down to "developer."

I started the rebuild the next week.

Anecdote: The LinkedIn Headline That Changed Everything

My old LinkedIn headline was something like: "CEO & Co-Founder | Healthcare Technology | Software Development"

It was technically accurate. It was also completely useless for positioning.

I changed it to: "Fractional CTO | Systems Architect | I prevent $20M rewrites for B2B platforms"

Within a week, the quality of inbound messages shifted. Instead of "do you do React?" I got: "We're worried about our architecture. Can we talk?"

Same experience. Same background. Different packaging. Wildly different response.

The headline isn't about describing what you've done. It's about signaling what problems you solve for people who have those problems.

Mini Checklist: Rebuilding Personal Brand at 20-30 Years In

[ ] Audited current public presence: does it reflect what you're selling now or what you did 10 years ago?
[ ] Identified the mis-positioning signals: are leads asking for the wrong things?
[ ] Extracted concrete metrics from your work: dollars, uptime, retention, costs avoided
[ ] Built case studies that emphasize outcomes, not just activities
[ ] Updated LinkedIn headline to signal problems solved, not job history
[ ] Created content that demonstrates thinking, not just credentials
[ ] Got external feedback: "what do you think I do?" test with strangers
[ ] Accepted that technical excellence doesn't speak for itself; it needs packaging