Tim Pile Book a session

Technical advising for founders, leaders, and builders.

Whether you're stretched too thin to go deep, or newer to the territory and want to know you're on solid ground. One focused session. A written recommendation.

Book a session

The session

A single sixty- to ninety-minute conversation, focused on whatever decision is in front of you. We work through the specifics together — tradeoffs, risks, the things you may not have considered.

Afterwards you get a written summary with concrete recommendations, so you have something to refer back to and share with your team.

Is this you?

Clients range from experienced technical leaders who are stretched too thin to go deep on one specific decision, to people newer to the technical side who want a senior read on whether they're on solid ground. What they share: a decision that's expensive to get wrong, and no independent person to check it against.

  • You feel behind on AI and want a clear read on where to actually spend your attention.
  • You shipped a prototype with AI assistance. It works, but you're not sure how fragile it is or what would break first under real load.
  • Security and compliance questionnaires are eating your week. You need a plan for SOC 2 that fits the size of the company.
  • You have data — events, logs, customer records — and no good way to turn it into answers anyone trusts.
  • You inherited a business-critical system and nobody fully understands it. You need to decide what to leave alone, what to wrap, and what to replace.
  • Your infrastructure bill keeps climbing and the explanations you're getting don't add up.

Who you're talking to

I'm a staff-level software engineer. My work spans infrastructure, backend, frontend, mobile, AI and LLM systems, data, and compliance — enough range to recognize where a problem actually lives, rather than where it first shows up.

I've taken products from nothing to production and spent years working closely with founders and executives, so I think about technical decisions in the context of the business around them, not just the code.

From clients

“[Testimonial quote]”
— [Client name, title]

How it works

  1. 01

    Book and pay

    Pick a time and pay up front. Send a short note about what you'd like to work through.

  2. 02

    Meet for 60–90 minutes

    We go deep on your decision. Bring whatever helps — diagrams, code, contracts, a blank page.

  3. 03

    Written summary

    Within a few days, a written recap with concrete recommendations you can act on or share.

Ongoing advisor arrangements available on request.