The prototype works. The next step does not.
Maybe it was vibe-coded. Maybe an agency built v1. Either way, it is real enough to matter and messy enough to need a plan.
Technical leadership for founders whose product is outrunning the plan.
Hey, I'm Ryan. I'm a technical advisor based in Portland, Maine. I help founders and product teams simplify, align on goals, and deliver the work that actually matters.
The product is real. The team around it is still catching up.
I work with founders and growing teams that need senior technical judgment, but do not yet need a full-time CTO, VP Engineering, or technical executive.
I am useful when the app exists, the stakes are rising, and the next step is no longer obvious. Sometimes that means strategy. Sometimes it means teaching the team better technical language. Sometimes it means getting hands on the keyboard.
The useful moment is usually before motion starts pretending to be progress.
The team is building plenty. Too much, maybe.
I help separate useful work from impressive-looking work, so engineering is not spending weeks on features nobody needed.
Sales, product, and engineering are not telling the same story.
I get the people in the room, translate between functions, and help the business stop playing telephone with itself.
How I help
Strategy, architecture, and execution.
The work usually starts with a question that has become too important to keep answering loosely.
What should we build? What should we stop building? How do we get sales, product, and engineering pointed at the same target?
Fractional technical leadership
Senior technical judgment before a full-time CTO or VP Engineering makes sense. Useful when the technical choices matter, but a full salary, benefits, and equity package would be premature.
Product, sales, and engineering alignment
Workshops, roadmap shaping, and translation across teams that are all using the same words a little differently. Useful when the CEO, sales lead, product lead, and a random engineer should be able to describe the business the same way.
Architecture and delivery review
A practical look at the codebase, data model, deployment path, team process, and the places progress keeps getting sticky. Useful when features drag across sprints, AI keeps fixing one bug by creating another, or deployment has become a haunted house.
AI adoption and technical gut checks
A clear-eyed read before fundraising, hiring, AI adoption, feasibility work, or a decision with real consequences. Useful when the room needs fewer case studies and more contact with reality.
A typical first pass
Start by making the mess visible.
Walk the product
We go through the app, the sales story, the roadmap, and the places where progress keeps getting stuck.
Find the real problem
I look at the codebase, data model, architecture, deployment path, team process, and customer signal.
Make the plan usable
We decide what to build, what not to build, what to fix first, and how to explain it so the team can move.
Lead or build where useful
I can facilitate, teach, review, lead engineers, and write TypeScript, Node, React, or web application code when strategy needs hands on the keyboard.
Start with the problem. Pick the shape after.
Some teams need a steady sounding board. Some need temporary technical leadership. Some need one focused pass through the mess with a flashlight and a red pen.
Ongoing advisory
A lightweight relationship for founders who want a senior technical brain nearby: reviewing decisions, shaping priorities, and helping the team avoid expensive detours.
Embedded leadership
A deeper role when the team needs interim technical leadership, better execution, hands-on engineering help, or support while hiring the permanent person.
Technical gut check
A short, concrete engagement around one knotty question: architecture, AI adoption, process, feasibility, team shape, or technical risk.
About
Founder scars, engineering depth, and a bias toward useful work.
Most recently, I founded Rally, an AI sales automation company that turned sales collateral, discovery calls, and customer context into landing pages, deal rooms, sales coaching, and research. I raised seed funding, lived inside the AI startup economy, and learned what breaks when ambition outruns clarity.
Before Rally, I led web application, workflow, live video, and prototype work at companies from startups to public-company scale. I came up through interaction design and front-end engineering before moving into product architecture, technical leadership, and company-building.
- Build less of the wrong thing
- Make the product, pitch, team, and codebase agree
- Use AI where it helps, not where it performs confidence
- Teach the technical language, not just the answer
- Stay close to customers, sales, and the messy truth
Contact
Trying to make the product, team, and codebase agree?
Book a 30-minute conversation or send a short note. Tell me what feels stuck, what you are trying to make true, and where the boulder is currently parked.