fCTO   Fractional CTO

Technology problems rarely show up as failures.

They show up as decisions no one revisits.

Cost drift. Architectural complexity. Systems that work but feel
expensive. Stacks that grew faster than understanding.


Patterns you may recognize

  • • Cost that feels high but is hard to challenge
  • • Systems that work but are expensive to maintain
  • • Tech stacks that grew faster than your understanding of them
  • • Teams shipping while decisions quietly compound
  • • Architectural choices that made sense then, but feel uncertain now
  • • Vendor relationships that started simple and became complex

This is common

This is not incompetence. This is what happens in execution mode. When you're focused on shipping, growing, and responding to immediate needs, decisions accumulate. Some were right at the time. Some were expedient. Some you inherited. The question isn't whether you made mistakes—it's whether you can still see which decisions still make sense and which ones don't.


My role

A second set of eyes. Senior technical judgment from someone who's seen these patterns before.

The work is separating "expensive but right" from "expensive and accidental." Understanding which decisions still make sense and which ones don't. Not prescribing solutions, but clarifying tradeoffs so you can decide.


How I work

  • • Short diagnostic conversations to understand your situation
  • • Pattern identification—recognizing what I've seen before
  • • Tradeoffs, not prescriptions
  • • Options, not mandates

If this sounds familiar, let's talk.

If you're unsure whether a tech decision still makes sense, reach out.

Start a conversation

Stephan Smith

Interim CTO | Technical Judgment

Boston based. I work with startups and growth-stage SMBs. Previously, I co-founded a company in the Techstars Boston cohort in 2018. I stay on top of tech and patterns so that operators and owners do not have to.

 

Stephan Smith, Technical Judgment for Startups and Growth-Stage SMBs

Who I work with

Small business CEOs and startup CEOs. Occasionally CFOs. Businesses with existing teams or vendors where technology decisions impact revenue or risk, and where clarity on those decisions matters.


Some References

Karen Kelly - Founder & CEO testimonial for Stephan Smith fractional CTO services
Karen Kelly
Founder & CEO

"Stephan and I work together frequently, and his collaborative nature is a huge plus. He brings clarity and practical solutions to our tech challenges, breaking down complex technical decisions into actionable steps. His ability to work alongside our team—rather than dictating solutions—has been invaluable. He understands growth-stage business challenges and provides guidance that aligns with both our immediate needs and long-term goals."


Yvan Castilloux - CEO of Augusta Care testimonial for Stephan Smith fractional CTO services
Yvan Castilloux
CEO of Augusta Care

“Stephan led our SOC2 compliance planning with a budget-conscious approach that balanced risk reduction with operational reality. He assessed our tech stack and delivered a practical roadmap that addressed compliance requirements without breaking the bank. His executive-level guidance gave us confidence we could meet our obligations while maintaining growth momentum."


Michelle Chao
Michelle Chao
COO of Phoenix Tailings

"Stephan worked with our team as we started to scale up and address security requirements. He assisted in our selection of security frameworks that matched our unique funding, IP, and cyber-security needs. His experience with growth-stage businesses provided us with options that matched our stage and immediate concerns. We hope to tap into his experience when our security requirements change."


Jesse Marple
Jesse Marple
Solutions Architect at Brytebridge

"We brought Stephan in to accelerate delivery on a critical integration project. He executed in record time, providing our front-end teams with Just-in-Time API resources as we finalized email providers, payment gateways, and AWS infrastructure decisions. His practical approach delivered both working solutions and best practices for API testing, JWT security, and a framework our team could extend. He restored delivery cadence and helped us ship a critical initiative in 4 weeks—exactly the execution leadership we needed."


Dan Zollmann
Dan Zollmann
CEO & Founder of Qase

"Stephan's contribution to Qase has been extraordinary: he found ways to reduce platform spend by 80%, decrease data migration time by 90%, all while improving Qase's resilience and security. Even more incredible is how he achieved this: instead of dictating solutions, he actively coached and mentored our existing staff, helping them to identify and implement new, better approaches. It's also rare to find a CTO equally comfortable in both the boardroom and the trenches. I highly recommend Stephan to any growth-stage business looking to optimize costs, improve delivery, and scale their team effectively."


One insight: AWS adds cost and complexity—often unnecessarily. For startups and growth-stage SMBs, reviewing an AWS bill is the first place to find solutions that reduce both.