CTO 1 on 1
Fast, focused, and outcome-driven — up to 2-hour 1 on 1 session where we tackle your most pressing technical or organizational challenge and leave with a concrete plan.
Moving from Magento 1.x to Shopify Plus while maintaining 10,000+ SKUs, custom integrations with ERP systems, and zero downtime during peak shopping seasons.
"We're stuck on React 17 because upgrading breaks our entire component library, but our best developers are unhappy because they want to use modern tools like Svelte, Solid and Bun."
"Knight Capital's 18-year trading empire collapsed overnight when old code caused $440 million in unauthorized stock purchases because they repurposed legacy trading algorithms without proper testing."
"Our PostgreSQL database buckles every time we hit 1,000 concurrent users, but we can't afford the $50K migration to a distributed architecture until next year."
"We spent 6 months building a microservices architecture for our 500-user SaaS app and now our AWS bill is $25K/month when a simple monolith would have cost us $1-2K or less."
"Our 15-year-old ERP system speaks XML while our new React app needs JSON APIs, so 80% of our sprint is spent building middleware instead of customer features."
"Discord's ScyllaDB cluster collapsed during an OS upgrade when one degraded disk caused a 50-minute authentication outage for 150+ million users because they couldn't handle the authentication lookups under load."
"HealthCare.gov had only 43% uptime at launch because they skipped caching, performance testing, and redundancy planning to meet the political deadline."
"We hardcoded the 8.5% tax rate in 47 different files to ship our e-commerce feature on time - now tax season requires a 3-developer manhunt to update every instance."
"Our QA team can test 20 features per sprint but development is shipping 35 - critical bugs are slipping into production because we have one tester for every four developers."
"I can't explain to the CEO why we need 2 sprints to refactor our authentication system when it 'works fine' - but every new login feature takes 3x longer because of our spaghetti code."
"Our checkout process works perfectly in staging but fails in production every Friday at 3 PM when our payment processor switches to weekend mode - we can't replicate their environment."
"A single production bug cost us $2,000 in salaries and 8 hours of developer time across 4 team members because our staging environment uses SQLite while production runs PostgreSQL."
"LinkedIn's ATS rejected our best senior engineer candidate because she had a 3-month employment gap, while AI-generated resumes from bootcamp grads sailed through to final interviews."
"Our Berlin team pushes code at 6 PM that breaks our San Francisco team's 9 AM standup, and by the time we debug it, Sydney has already started their sprint planning with broken builds."
"When we grew from 15 to 45 engineers, our one-hour team standup became a status theater where developers waited 45 minutes to speak for 2 minutes about yesterday's work."
"Engineering spent 3 months building a perfect real-time analytics dashboard that marketing can't use because they needed simple daily email reports, not live data streams."
"Our senior developer gets interrupted by Slack 47 times per day and says it takes 23 minutes to get back into deep focus after each notification - actual coding happens after 6 PM."
"Remote developers are checking emails 40% more after hours just to stay visible while office employees get promoted because they're in the 'casual hallway conversations' where real decisions happen."
Choose a time via Calendly (or email me). You'll get a short prep questionnaire to help us make the most of our time together.
Share the challenge, context, and what success looks like so I can come prepared with relevant insights and examples.
We'll clarify the root cause, explore 2–3 strategic options, and co-create an actionable plan (steps, owners, milestones). You'll also receive a concise summary afterwards with clear next steps.
Technical leaders facing complex challenges that need strategic thinking and practical solutions
Leading technical strategy and managing complex architectural decisions
Stepping into leadership roles and managing growing teams
Building and scaling technical products from the ground up
On a problem that needs fresh perspective and strategic thinking
Clear direction and actionable solutions, not theoretical advice
Peer-level partnership without the premium consultant pricing
The goal of these sessions is to bring clarity, breakthrough and organized thinking to difficult problems you might face. This doesn't mean we will solve all of your problems right away (sorry) but help you untangle what is a problem and how to move forward.
"The most valuable thing wasn't the solution—it was finally understanding what problem we were actually trying to solve."
I’ve led engineering teams, modernized complex systems, and advised companies at critical inflection points. A Deep Dive gives you a fresh set of eyes, fast pressure‑testing of your thinking, and a concrete, practical plan to move forward.
Teams leave with an initial remediation plan for critical technical debt, a small-scope experiment to validate a product assumption, or a clear roadmap for scaling infrastructure safely.
Sessions are confidential and tailored to your context. After the call you’ll receive a concise summary with next steps, owners, estimated effort, and suggested checkpoints to keep momentum. If you want follow-up support, we can scope short engagements to help implement the plan.
Can we help?
Tell us about your idea — we’ll figure out how to help, one step at a time.
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