About
I live in Plainfield, Illinois. I lead technology at Empower Health Services. Nineteen years in the gap between “we need this” and “that isn’t a product.” Ten years at Empower Health Services: making a five-person team able to take the yes with me.
Path
2007
Wellness Inc.
First real job. Desk was a rolling wire shopping cart. Binders of Palm Z22s loaded with ePHI arrived every few hours. Job: hot-sync → CSV → floppy → jefferson.local. No Wi-Fi. Clouds were weather. Apple hardware in healthcare was considered taboo. We did it anyway.
2010
UnitedHealth Group / Optum
Wellness Inc. was acquired. I landed on UNH’s first Mac OS and mobile teams, standardized and shipped a thousand customized iOS devices a week, and built the first mobile-friendly surfaces the org had. Applied for the job that was my actual work. Heard crickets. Turned in the badge. Sometimes no is how a career starts.
2012
IC&MC · Richard J. Stephenson
Private technical advisor to a merchant banker and family — estates, aviation, ventures, a fiber ring when residential fiber was a joke, fax machines on yachts because that was “compliant.” White-glove, 24/7, NSA-grade security, seven-figure cost takeouts. Masterclass in completing impossible requests and celebrating life.
2013
HAWA · Co-founder
Co-founded Health As We Age. HIPAA portals, nurse PHR, telehealth. An “IT unicorn” in the way that actually matters: tiny team, real product, regulated environment. Burnout showed up quietly. Then a text.
2016
Empower Health Services
Gary Fine. Five words. Day one was startup-garage energy and a desk that was a wire rack again. Ten years later the job is the shop: five people, the product built in-house. A Monday that actually means something. I still say yes. I still ship. I still make yesterday’s job obsolete so they can take the next one.
The shop
I do not scale by hiring. I scale by making five people dangerous — open work, a real cadence, and a boss who unblocks instead of collecting status. Coordination tax kills more products than missing features. This is the shop that runs a national HIPAA platform.
01
The product surface. What members and clients actually touch.
02
Identity, APIs, the path from demo to live.
03
Clinical truth. The reports a client will argue about.
04
Whatever has to exist by Monday and does not have a name yet.
05
The audit. MFA, CASA, the reason we still have Google scopes.
How I lead
01
Markdown over mystery. Tickets into GitHub. Monday Dev Collective with a master agenda, not standup theater. If the team can see the week, they can move it without me in the room.
02
I moved to a bullpen desk so I would stop being a closed door. Presence is a leadership tool. So is knowing when to take the call somewhere else.
03
Agents take the first pass. Two developers own the human gate. I take the aesthetic and the Friday demo. The shop gets faster because the floor is higher — not because I type more.
04
Tickets are data points across the environment. We close them as they appear. Vendor hours put on standby. Money we used to rent now pays for a full-time seat with benefits. Headcount is a last resort. Leverage is the job.
05
A shop that still needs me on every push to demo is a shop I have not finished. The next job is handing QC to someone I trust — and being able to sleep.
In the room
“WOW — Lee is instrumental in EVERYTHING EHS. He is a great ambassador moving us forward with technology in every aspect of the company. I like to think of him as our Chief Innovation Officer.”
“I doubt I will ever have a professional superior that is as knowledgeable, approachable, and patient as you are.”
How I work
01
I learned this as a private technical advisor when the request was fiber around an estate, a fax on a yacht, or a plane that had to work. The tech often did not exist. The answer was still yes — and then the work to make it true.
02
Coordination tax kills more products than missing features. Five people who own the stack will outrun fifty who wait on a ticket queue. AI is a force multiplier. The secret sauce is still the team.
03
HIPAA, NIST, MFA, disaster recovery, dependency patches, first-pass deploy rates. Innovation that cannot survive an audit is a demo. I treat security and QA as product, not afterthought.
04
I would rather over-document in Markdown than become a mystery. If the team can see the work, they can move it. Asynchronous, decentralized collaboration is not a slogan. It is how we ship.
A small shop, run well, is not a compromise. High taste. A bias to ship. A team that can take the next yes without waiting on me.
Write