I direct AI to ship real software.
Founder of Serendipity Technology, working as a fractional CTO and custom development partner, and open to the right full-time role.
About
I'm Troy Shimkus, founder of Serendipity Technology, where I work as a fractional CTO and build custom software end to end. The work leans hard on AI-directed engineering: I own the architecture, the security, and the final call, and AI does the heavy lifting under that direction. The result is senior judgment with agency-scale output, without the agency overhead.
I spent 12 years at PowerSchool and more than 20 years in technology overall, leading product delivery and data programs across EdTech and the public sector. I care about the same things on every project: clear product thinking, clean data, and systems that actually ship. I'm building full-time now and open to the right full-time engagement.
Currently
Independent, running Serendipity Technology, and open to the right full-time engagement. If you need a fractional CTO or a custom build, or you're hiring for a senior technical leadership role, I'd like to hear from you.
Projects
Products I designed, built, and run through Serendipity Technology. Proof the approach ships.
Upfront
Send a custom estimate, get it approved, and get paid, all on one branded page. Money goes straight to the client's own Stripe account. A multitenant CRM built around quote-to-payment for service businesses.
Membership Database
A multitenant membership platform for clubs, chapters, and nonprofits: dues, events, volunteer hours, and reporting, with each organization's data kept separate.
PrecinctWins
Handles statewide voter data sets with large-scale data processing and analytics, plus precinct-level mapping and outreach. Grew from field mapping into a full platform working millions of voter records, and adapts to donor engagement for nonprofits.
Other projects and platforms
More of what's running under the Serendipity Technology umbrella.
Resume
20+ years in technology, 12 of them at PowerSchool, now building full-time as a fractional CTO and custom development partner.
AI-Directed Engineering
- I own the architecture, the security, and the final call
- AI does the heavy lifting under that direction
- Agency-scale output without the agency overhead
Fractional CTO & Technical Leadership
- Strategic technical leadership for organizations that can't hire a full-time CTO
- Architecture and security review, vendor decisions, build-versus-buy
- AI adoption that fits the organization
Product Delivery
- Align stakeholders, shape roadmaps, coach cross-functional teams
- Plan, execute, and scale with clear outcomes
- Bridge technical and non-technical to ship the right thing
Data Programs
- Dashboards, secure data flows, and integrations (APIs, ETL)
- Clean data and stakeholder-ready reporting
- K-12 and civic data experience
Experience
Founder, Serendipity Technology
- Fractional CTO: technology strategy, architecture and security review, vendor decisions, and AI adoption.
- Custom software development end to end, built with AI-directed engineering.
- Designed, built, and run Upfront (quote-to-payment), the Membership Database, and PrecinctWins (statewide voter data and analytics).
12 years · past role
PowerSchool
- Led customization of SaaS dashboards for 150+ school districts (100k+ students).
- Standardized deployment and documentation, reducing onboarding time.
- Aligned technical and non-technical stakeholders to district outcomes and renewals.
- Partnered with district leadership on adoption strategies and product improvements.
- Strengthened retention and trust through hands-on issue resolution.
Consultant (Independent), Software Integration & Solutions
- Delivered 20+ solutions for small businesses and nonprofits.
- Built web apps, Dockerized infrastructure, API integrations, and AI-powered tools.
- Implemented marketing automation pipelines (Mautic, RabbitMQ, MySQL).
Past civic role
City Commissioner, City of Deltona, FL
- Guided leadership transition; led City Manager recruitment and compensation strategy.
- Launched public dashboards to improve transparency and civic trust.
President, Deltona Strong, LLC (Nonprofit)
- Founded community resilience nonprofit; raised $40k+ for families in need.
- Launched community garden and emergency hotline with local partners.
Innovative Learning Specialist, Lake County Schools, FL
- Rolled out district-wide software/hardware with tailored educator training.
Contact
Let's connect
Looking for a fractional CTO, a custom software build, or talking about a full-time role? Send a note and I'll get back to you.
hello@troyshimkus.com