Last updated: 08/17/2026
Note: this is currently a work-in-progress.
November 2023 through April 2025
OptHealth's technology was out-of-date, not functioning well, difficult to extend and the only engineer assigned to the project was required to spend over 90% of their time on responding to urgent operations needs and high-priority bug reports and close to being burnt out. After a period of resource constraints, OptHealth again had the resources to re-invest in their technology stack, but they had difficulty finding someone willing to lead the engineering team out of hole they found themselves in.
OptHealth had a completely up-to-date technology stack, with a rebuilt core, a highly functional engineering team that spent less than 10% of their time on bug fixes, and the original engineer was able to continue working calling me "the best mentor they ever had" and "changing the trajectory of their life".
OptHealth was now in a great position to raise a series A and scale their technology platform.
hired as the "head of engineering"
reported directly to the CEO with the engineering team reporting to me
collaborated with a project manager
led the entire effort from evidence gathering, to analysis, to presenting options to stakeholders, to hiring and building out the engineering team, to planning and execution
OptHealth is a seed funded tele-health tech startup based in San Francisco, California and founded in 2020. Due to resource constraints, the original development team was not able to stay with the company and there was a long period where they were unable to invest in the technology they had built.
core web-app:
integrated with
iOS app built by an outside agency with React Native
software had to be HIPAA compliant
none of the software packages had been updated since 2020
At the start I:
interviewed the engineer, project manager (who had recently joined), and the executive and product teams
performed a technology analysis and produced a report detailing:
executive score summary for each category, for example (numbers do not match actual report)
| Category | Score (Out of 10) | Goal |
|---|---|---|
| Security | 2 | 8 |
| Reliability & Qualify of Service | 3 | 4 |
| Integrations | 1.5 | 7 |
| Eng. Team Performance | 4 | 10 |
| Infrastructure | 2 | 10 |
| Compliance | 5 | 10 |
"score" is the current situation calculated based on the report details and the "goal" is the level I determined OptHealth should be at for the stage of the company and industry. The "goal" values would increase as the company scaled and/or raised money.
investment need to reach each "goal" as expressed in "engineering person hours"
a high level overview of what I considered to be immediate risks and long-term risks
the rest of the report was a thorough breakdown of the specific reasons for each score and where they come from
I then worked with the CEO and other stakeholders to determine priorities and desired timelines
I then worked with the CEO and other stakeholders to develop a resource plan
after there was agreement on direction and resources I developed an execution plan based on the expected change in resources
additional issue: development and staging environments did not match production
additional issue: development environment was non-functional so debugging and bugfixes were done live in production
expand the engineering team by 2 full time members and bring in additional contractors to provide supportive services including additional engineering effort and ux design
migrate from the drchrono to Healthie EHR
lead the engineers on:
mentoring and guiding the less experienced engineers
led and hired a contractor team to build a new native iOS app
provided team and progress updates to executive team
created and presented regular updates on technology stack status and goals
a continuation of the original report so we could all track progress and make decisions together efficiently)
