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.
This is not a menu of fractional CTO hours. It is a set of ways to connect product ambition, technical choices, GTM reality, and execution.
The right shape depends on whether you need regular strategic help, someone inside the work, or one focused pass through a consequential question.
Scope
Ongoing advisory
When
You need regular strategic technical help before a full-time CTO, VP Engineering, or technical executive makes sense.
Role
A senior partner across product, engineering, GTM, hiring, and AI adoption: reviewing tradeoffs, shaping priorities, and keeping the technical story connected to the business.
Output
Clearer decisions, sharper sequencing, and fewer moments where engineering has to guess what matters most.
Scope
Embedded leadership
When
The company needs someone inside the work: aligning teams, shaping roadmap, guiding engineers, or helping while the permanent leadership shape comes together.
Role
I slot into the operating rhythm: clarifying priorities, reviewing architecture, unblocking delivery, and building selectively where implementation helps the strategy.
Output
A narrower roadmap, a calmer team, and forward motion against the right target.
Scope
Technical gut check
When
One knotty problem needs a focused assessment: architecture risk, product direction, AI-built prototype limits, diligence prep, hiring plan, roadmap confusion, or team drag.
Role
A practical pass through the product, codebase, architecture, team context, and business pressure behind the question.
Output
A concrete read on what is real, what is risky, what tradeoffs matter, and what should happen next.
About
Founder scars, engineering depth, and a bias toward useful work.
I have over 15 years of technical and leadership experience helping teams build, grow, and deliver. 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
Send the messy version.
The problem does not need to be neatly packaged. Send the prototype, the strange bug, the roadmap, the AI-generated codebase, the pitch deck concern, or the team confusion.
If I can help, we will find the shape quickly. If I cannot, I will say so.
A useful first note might include:
- What you are trying to make true
- Where progress is getting stuck
- What you have already tried
- Any deadline, raise, launch, or hiring decision in the background
First call: 30 minutes, practical and low ceremony. We will talk through the situation, separate symptoms from the real problem, and decide on a useful next step.