Coaching
Practical guidance for builders shipping real products
15 years shipping production software. FDA-cleared medical devices. Teams scaled from 0 to 50. Now building AI products in public.
Whether you're an engineer, a technical founder, or a domain expert building with AI tools, I help you ship with confidence and grow your impact.
Ready to dive in? Book a session directly. Want to talk it through first? Schedule a free intro call.
How Coaching Works
Format
1:1 video calls where we work through your specific challenge
What You Get
- Tactical frameworks from real experience, not generic best practices
- Honest perspective on trade-offs from someone who's made these decisions
- Follow-up async support via Slack/email between sessions
Flexibility
Book a single session to tackle a specific problem, or schedule multiple sessions for ongoing support
Booking
Choose your track below and schedule via my calendar
Pricing
$300/hour
Book a single session or multiple sessions as needed. Includes brief async follow-up for clarifying questions.
One session that prevents a bad architecture decision or accelerates AI adoption by weeks pays for itself many times over. Most clients resolve their challenge in 1-2 sessions.
Claude Code Basics
For builders new to Claude Code or the terminal who want to use AI tools confidently
Who It's For
- You installed Claude Code but the terminal still feels foreign
- You're not a traditional engineer — PM, designer, founder, or domain expert — building with AI tools
- You're using Claude Code or Cursor but flying blind, unsure what's happening under the hood
- You want to understand enough to make informed decisions, without needing a CS degree
Common Topics
- Terminal basics that make Claude Code feel less foreign
- What Claude Code is actually doing — and what to trust it with
- Setting up your first project the right way (CLAUDE.md, repo hygiene, safe defaults)
- Context windows, MCP servers, and skills explained without the jargon
- Reading and reviewing AI-generated code with confidence
- When to slow down: spotting risky changes before you ship
What You'll Walk Away With
- A working Claude Code setup tuned to your project, so you stop fighting the tool
- Enough understanding of what's happening under the hood to make informed choices
- A clear sense of when to trust AI output and when to slow down
Technical Coaching
For builders shipping AI-powered products and making architectural decisions
Who It's For
- Builders shipping production features and making architectural choices
- Developers and creators learning to use Claude Code, Cursor, or similar AI tools effectively
- Technical professionals navigating complex trade-offs in AI integration
- Anyone stuck on a hard technical problem and looking for a sounding board
Common Topics
- System architecture and design decisions
- AI integration: production LLM features, RAG, agents, tool use
- AI coding workflows: Claude Code, Cursor, MCP servers, practical setup
- Rails application architecture and ViewComponents
- Code and architecture reviews
- Engineering in regulated environments (healthcare, fintech)
What You'll Walk Away With
- A decision on your architecture question with documented tradeoffs, so your team can move forward
- A working Claude Code setup tuned to your codebase, so you stop fighting the tool
- A clear plan for your AI feature with the risks identified upfront, so you don't discover them in production
Career & Leadership Coaching
For technical professionals growing their impact and leaders scaling teams
Who It's For
- Technical professionals who want to grow their influence and impact
- Senior ICs considering leadership transitions (or deciding not to)
- First-time engineering managers, directors, or CTOs navigating growth
- Leaders scaling teams and making organizational decisions
Common Topics
For Senior Individual Contributors
- Growing technical influence without formal authority
- Career navigation: IC vs. management track (and how to decide)
- Staff/Principal engineer growth and expectations
- Technical leadership and high-stakes decision-making
For Engineering Leaders
- Scaling engineering teams (especially the chaotic 10→50 phase)
- Hiring strategy, team structure, and organizational design
- Managing technical debt while maintaining velocity
- Leadership transitions: IC → manager → director → CTO
What You'll Walk Away With
- A clear decision on IC vs management (or staff/principal growth) with a concrete plan for the next 6 months
- A hiring strategy and team structure that fits your stage, so you stop guessing at org design
- A framework for managing tech debt that your team can actually follow, so velocity stops degrading
What Clients Say
"I discovered Damian on YouTube. I found his videos especially clear-headed. I booked a couple of private sessions to discuss OpenClaw, and to my delight, he was equally clear-headed in person."
"Working with Damian was one of the most productive technical sessions we've had. He quickly understood where we were with AI tooling and gave us immediately actionable advice, not generic frameworks. He identified gaps we hadn't considered, walked us through how he architects agent loops in production, and helped us think through our product-level agent strategy without over-engineering it. If you're a technical founder trying to move faster with AI, Damian is the person to talk to."
Why Work With Me
Still Building
I'm a Senior Software Engineer at August Health building clinical software, and I'm shipping AI products in public through my YouTube channel and SaaS projects. My advice comes from what I'm doing right now, not what I did years ago.
Shipped at Every Level
I've shipped FDA-cleared medical device software, scaled an engineering team from 0 to 50 as CTO, and built AI-powered products from scratch. I've seen what works across different stages and contexts.
Both Paths, First-Hand
15 years as an individual contributor and 5+ years as a CTO. I can speak credibly to both the IC and leadership experience because I've lived both and chose to return to building.
Frequently Asked Questions
Is coaching right for me?
Coaching is for specific, bounded problems where you need an outside perspective:
- You're stuck on a technical decision and need help thinking through trade-offs
- You're building something with AI tools and want guidance from someone doing it daily
- You're navigating a career transition and want perspective from someone who's done it
- You need to get unblocked and move forward
Coaching is not right if:
- You need ongoing technical leadership or implementation help for your team (that's a Production AI Retainer)
- You want someone to implement the solution, not just guide you (that's consulting)
I'm not a traditional software engineer. Is this for me?
Yes. My coaching clients include founders, product managers, and domain experts who are building with AI tools. If you're shipping something real and want practical guidance, we can work together. The substance is what matters, not your job title.
What's the difference between coaching and a retainer?
Coaching: One-off or occasional 1:1 sessions for specific individual problems. You drive the agenda, I provide perspective and frameworks. Hourly.
Foundation Sprint + Retainer: A 2-week paid trial that produces a written architectural assessment and one shipped foundation piece, optionally extending into an ongoing retainer at the intensity your team needs (Advisory, Embedded, or Full). Team-level work in your codebase. See How We Work Together for details.
If you're not sure which fits, book a free intro call and I'll tell you honestly.
Which track do I need?
Simple test:
- You're new to Claude Code or the terminal and want to use AI tools confidently? → Claude Code Basics
- Your challenge is about code, architecture, or implementation? → Technical Coaching
- Your challenge is about people, career, or organizational decisions? → Career & Leadership Coaching
Many people book sessions in different tracks at different times. That's fine.
How many sessions will I need?
It depends on your challenge. Some problems get resolved in a single focused session. Others benefit from 3-5 sessions over a few weeks.
After our first session, I'll give you my honest take on whether you'd benefit from follow-up sessions or if you're good to go.
Do you only work with Rails teams?
No. My technical coaching works across stacks. I've advised teams on Node, Python, Go, and others. Rails is a strength, but the architectural thinking applies broadly.
The Rails LLM Course is Rails-specific, but coaching is not.
What if I'm not sure what I need?
Book a free 30-minute intro call. We'll talk through what you're trying to accomplish, and I'll tell you honestly whether coaching makes sense, which track fits, or if you'd be better served by a Production AI Retainer for team-level work.
No pitch deck. No pressure. Just a conversation.
What's your background?
15+ years building production software. Previously CTO at Buoy Software where I grew the engineering team from 0 to 50+ engineers and shipped FDA-cleared medical device software.
Currently Senior Software Engineer at August Health, building AI products in public on my YouTube channel (AI in Production), and writing a book on building LLM applications with Ruby on Rails. I coach and advise because I still build every day.
Not Sure Where to Start?
Book a free 30-minute intro call. We'll talk through what you're trying to accomplish, and I'll tell you honestly whether coaching makes sense and which track fits your needs.
No pitch deck. No pressure. Just a conversation to see if there's a fit.