Architected for Lift.
Advisory CTO oversight and systems hardening for growth-stage organizations.
We remove the friction so you can scale with precision.
Success shouldn't feel fragile.
Most companies hit a ceiling between $2M and $10M. Your prototypes are brittle, your data is siloed, and your team is drowning in manual workarounds. You’re hiring builders (developers), but you’re missing the Architect.
Brittle Scaffolding: Unstructured AI and no-code "hacks" that shatter at scale.
Manual Glue: High-value talent wasted on low-value data syncing.
Technical Debt: Quick fixes from last year are today’s bottlenecks.
Leadership Gap: You need strategic oversight, not just more code.
Our Services
Systems Integrity Audits
We perform a comprehensive deep dive of your current technical stack. We look past the UI to find the brittle integrations, manual data leaks, and architectural gaps that are currently acting as an anchor on your team’s productivity.
Deliverable: A full Technical Integrity Report and a prioritized 90-day stabilization roadmap.
Engagement: Fixed-price. No surprises.
Fractional CTO Advisory
For firms that need a veteran at the controls but aren't ready for a full-time executive hire. We provide ongoing oversight of your technical roadmap, vendor management, and systems hardening to ensure your tech evolves as fast as your revenue.
Deliverable: Ongoing strategic alignment and architectural oversight.
Engagement: Fixed-price monthly retainer.
Technical Vetting & Hiring
The most expensive mistake a growth-stage brand makes is hiring the wrong engineers. We act as your technical proxy, vetting candidates for architectural thinking, code integrity, and long-term fit so you can hire with total confidence.
Deliverable: Comprehensive candidate assessment and "Go/No-Go" recommendations.
Engagement: Per-role or project-based.
Meet the Founder
Chris Grey • Founder and Advisory CTO
Veteran Oversight for Growth-Stage Firms.
"With 25+ years of experience navigating the technical evolution of scaling companies, I founded Wingtip to serve as the seasoned technical guidance for founders hitting the complexity ceiling. My career has been defined by stabilizing systems under pressure—moving organizations from the fragile, 'patchwork' foundations of their early days to the hardened, high-integrity architecture required for mid-market success.
I don’t just offer advice; I provide the Structural Integrity Assessments and architectural blueprints that turn technical debt into operational lift. Whether I’m auditing a legacy stack or vetting your next lead engineer, my goal is to ensure your technology acts as a tailwind, not an anchor, as you scale toward your next major milestone."
Clear the Runway.
Stop patching and start building a foundation that can handle your next stage of growth. Schedule a brief 10-minute discovery call to see if a Structural Integrity Assessment is the right move for your current architecture.
