CTO 1 on 1

CTO Deep Dive — 2 Hours, Clear Plan

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.

Book Deep Dive

Major Themes With Specific Real-World Examples

System & Architecture

Legacy System Modernization Burden

"Our core product is a Rails 6 monolith with a 90-minute test suite, and every new feature risks breaking something mission-critical. We can't upgrade our gems, and our frontend is a mess of javascript technologies."

Developer Experience vs. Stability Trap

"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."

Technical Debt Avalanche

"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."

Scaling Under Resource Constraints

"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."

Over-Engineering vs Under-Engineering Dilemma

"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."

Integration Complexity Nightmare

"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."

Infrastructure Bottlenecks at Scale

"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.""

Product & Quality

Speed vs Quality Paradox

"HealthCare.gov had only 43% uptime at launch because they skipped caching, performance testing, and redundancy planning to meet the political deadline."

Technical Debt Masquerading as Business Velocity

"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."

Quality Assurance Resource Shortfall

"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."

Code Quality Visibility Gap

"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."

End-to-End Testing Complexity

"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."

Production Bug Mysteries

"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."

Team & Collaboration

Talent Shortage and Skill Gap Crisis

"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."

Remote Team Coordination Friction

"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."

Scaling Team Leadership Structures

"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."

Cross-Functional Alignment Breakdown

"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."

Communication and Context Switching Overload

"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 Work Visibility and Growth Challenges

"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."

How It Works

Book your slot

Choose a time via Calendly (or email me). You’ll get a short prep questionnaire.

Prep together

Share the challenge, context, and what success looks like so I can come prepared.

Deep Dive — 2 hours

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.

Who This Is For

CTOs, VPs of Engineering, Directors, Tech leads stepping into leadership, and Founders managing technical teams.

✔️ You’re stuck on a problem that needs fresh perspective
✔️ You want clarity and direction, not another theory
✔️ You’d value peer-level collaboration without the $500/hr consultant fee

Investment

$250

Up to 2 hours of focused advisory and a concise action plan.

Book Your Deep Dive Now

Why This Works

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."
— Engineering Director, Series B startup

Real-world experience, practical focus

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.

What you actually get

Practical outcomes — not theory
Highest-impact actions prioritized
Clear ownership and short milestones
Measurable progress from day one

Typical session results

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.

What happens after

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.

Stuck on your product?

Let’s get you moving again.

We’ll help you unblock, refocus, and deliver — with real developers on your side.

Get Started

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