Startup Technical Strategy
Roadmaps, org design, engineering culture, and the strategic moves behind technical companies that scale.
40 posts · page 2 of 2
- Startup Technical Strategy
The VP Engineering Hire: What Founders Get Wrong
The VP of Engineering hire is one of the highest stakes decisions a technical founder makes. Most founders make it too early, hire the wrong archetype, or set the new leader up to fail. Here is what actually goes wrong and how to avoid it.
12 min read
- Startup Technical Strategy
The First Director of Engineering: A Decision Framework
How to decide when to hire a Director of Engineering, what to look for, and what mistakes make this hire one of the most expensive in a startup's growth.
12 min read
- Startup Technical Strategy
The First Engineering Manager: When and How to Hire
The specific signals that tell you it is time to hire your first engineering manager -- and the mistakes that make this transition harder than it needs to be.
12 min read
- Startup Technical Strategy
The Internal Tooling Roadmap: Why It Matters As Much As the Product Roadmap
Internal tooling without a roadmap becomes invisible technical debt. Here is how to plan and prioritize it alongside the product.
12 min read
- Startup Technical Strategy
The Engineering Operations Team: When You Need One
The signals that tell you it is time to invest in a dedicated engineering operations function and what that investment actually looks like at startup scale.
12 min read
- Startup Technical Strategy
The Sales Engineering Function: A Founder Engineer's Best Asset
Sales engineering is the function that turns technical complexity into a closed deal. Founder engineers who invest in it win enterprise accounts. The ones who treat it as optional lose them to competitors who show up prepared.
12 min read
- Startup Technical Strategy
The Engineer Customer Conversation: Patterns That Yield Insight
How engineers can talk to customers in a way that surfaces real product problems instead of feature requests and validation-seeking.
12 min read
- Startup Technical Strategy
The Customer Feedback Pipeline Every SaaS Should Have
The feedback pipeline that turns customer signals into product decisions without a full customer success team or a dedicated research operation.
12 min read
- Startup Technical Strategy
The Build Measure Learn Loop for Engineers
How engineers apply the build-measure-learn loop in practice: what to instrument, how to define the experiment, and when to iterate versus when to pivot.
12 min read
- Startup Technical Strategy
The Three Layer Engineering Roadmap: Run, Grow, Transform
Most engineering roadmaps fail because they treat all work as equal. The three-layer model separates keeping the lights on from growing the product from changing the architecture. That separation is where planning gets honest.
12 min read
- Startup Technical Strategy
The Engineering OKR That Works
How to write engineering OKRs that create alignment without bureaucracy and measure what actually matters for the team's health and output.
12 min read
- Startup Technical Strategy
The Quality vs Speed Tradeoff: A False Dichotomy
The quality versus speed debate is a distraction. The real question is where you are trading permanence for optionality, and whether you know which you are doing.
12 min read
- Startup Technical Strategy
The Engineering Velocity Question: How Fast Should You Be Shipping?
The right answer to engineering velocity is not 'as fast as possible' -- it is specific to the stage, the product maturity, and what the team is optimizing for.
12 min read
- Startup Technical Strategy
The Roadmap vs Reality Gap: A Founder Discussion
Every startup roadmap is fiction on day one. The ones that survive contact with reality are the ones built around honest constraints, not aspirational calendars.
12 min read
- Startup Technical Strategy
The Technical Founder's Quarterly Review
The quarterly review is not a status meeting. It is the discipline that keeps a technical founder's engineering organization aligned with business reality. Here is the format that works without consuming the week.
12 min read
- Startup Technical Strategy
The Technical Due Diligence Checklist for Investors
Technical due diligence surfaces the engineering risks that financial models miss. The checklist that follows is the one I use on real deals, written plainly so founders and investors can use it without translation.
12 min read