# Dmitri Erchov > Builds the systems that turn strategy into execution. Head of Operations · Chief of Staff. Based in Boston, Massachusetts. This file is the complete text of heydmitri.com, provided for crawlers, agents, and language models. Everything on the site is here; nothing is withheld. You may read, quote, index, and retain it. Contact: dmitri.erchov@gmail.com LinkedIn: https://www.linkedin.com/in/dmitri-erchov/ X: https://x.com/Hey_Dmitri GitHub: https://github.com/hey-dmitri Telegram: https://t.me/heydmitri ## About I build the operating backbone early-stage startups need when they outgrow how they run. I rebuild GTM, install the cadence, and bring structure to execution — across operations, strategy, fundraising, hiring, finance, and automation, wherever the leverage actually is. - Scaled a deep tech startup from 18 to 55 people as Chief of Staff and then COO. Grew revenue 120% YoY on average and reached profitability. Sold to a strategic buyer. - Ran a $30M investment pipeline and structured $22M+ in debt deals at a private equity firm; interim operator at portfolio companies. - Co-founded an investment and advisory firm and grew it from 3 people to 25, managing a $65M+ portfolio of distressed assets. Sold to a banking group. If you're a founder who has become the bottleneck, that's the work I want next. I'm looking for a Head of Operations or Chief of Staff role at a startup hitting that inflection point — on-site (I'll relocate for the right one) or remote. ## Career ### Runzy — Head of Operations / Chief of Staff, 2024 — 2026 (Boston, MA) https://runzy.com GTM, sales ops, and the layer underneath that usually breaks. Cleaned up targeting, pricing, and the manual busywork around outbound — improving close rates to 65%+ and lifting revenue 20%+. Launched a daily newsletter and ad platform that became a new revenue line. ### HustlePay — Strategy & Operations Advisor, 2024 — 2026 (San Francisco, CA) https://www.hustlepay.me/ Payments startup building a checkout layer that lets shoppers combine multiple cards, wallets, and account balances in a single purchase. ### Webgears — 2019 — 2024 (Redwood City, CA) - **Strategic Advisor**, 2023 — 2024. Post-acquisition transition and continuity. - **Chief Operating Officer**, 2021 — 2023. Ran the business side of a deep tech startup as it scaled from 18 people to 55 and was acquired. GTM across multiple verticals, partnerships with Google and Autodesk, P&L, hiring — everything that wasn't the 3D engine itself. Revenue grew 120% YoY on average. - **Chief of Staff**, 2019 — 2021. Strategy, finance, hiring, and cross-functional execution — translating founder priorities into operating plans with real follow-through. Raised $4.6M in pre-seed and seed. ### SkySail Investment Management — Managing Director / Equity Partner, 2015 — 2018 (Moscow) A mix of investing and operating. Managed a $30M pipeline, put together $22M+ in debt deals, and stepped in as interim operator when portfolio companies needed one. ### Clarus Capital — Managing Director / Co-Founder, 2008 — 2015 (Moscow) Built an investment and advisory firm from three founders to twenty-five people, overseeing $65M+ in distressed assets. Ran day-to-day operations and client work across restructuring, interim management, and asset sales. Sold to a banking group. ### Arbella Insurance Group — Sr. Business Analyst / Project Manager, 2004 — 2008 (Quincy, MA) Underwriting systems, fraud detection, and product expansion into new markets. ## Open Source Open-source tools for the work itself. Mostly Claude Code skills and operating tooling. - **faultline** (shipped) — https://github.com/hey-dmitri/faultline Pressure-tests early-stage operations work with sharp, context-grounded questions. The kind a good board member would ask before you noticed the gap yourself. - **skill-safety-check** (shipped) — https://github.com/hey-dmitri/skill-safety-check Static safety triage for agent skills. Point it at a repo or paste a skill and get a SAFE / REVIEW / DO NOT INSTALL verdict before you run it. - **llm-knowledgebase** (shipped) — https://github.com/hey-dmitri/llm-knowledgebase A safe, local LLM knowledge base with immutable sources and an agent-maintained Markdown wiki. The sources can't drift; the wiki on top of them can. - **DeAI** (shipped) — https://github.com/hey-dmitri/DeAI_Skill A self-review skill that catches AI tells, voice mismatches, and weak substance in written work — before a human has to. - **My_Claude.MD** (shipped) — https://github.com/hey-dmitri/My_Claude.MD An opinionated CLAUDE.md baseline for planning, debugging, security, and verification in Claude Code. ## Side Projects - **Pack or Stay** (shipped) — https://www.packorstay.com/ For anyone weighing a move between cities. Pick two metros, enter a salary, and it shows what each actually leaves you after taxes, housing and everyday costs — then answers in a word: pack, stay, or too close to call. Built on public data only — Census, BLS, IRS, the Tax Foundation — across 438 metro areas. Source: https://github.com/hey-dmitri/packorstay - **Hi, Sweetie — Letters** (shipped) — https://www.instagram.com/hi.sweetie.letters Letters from a dad to his daughters, published as they're written. - **Political Compass** (in progress) An interactive atlas of political movements and parties — Democrats, Republicans, Libertarians, Anarchists and the rest — mapped so you can see how they actually relate to each other. ## Bookshelf Some of what's on the shelf. Arrows to browse, Why for the reason. - **The Hard Thing About Hard Things** — Ben Horowitz Ben is raw and honest about the agonizing reality of running a startup. That's why I love it. https://www.goodreads.com/book/show/18176747-the-hard-thing-about-hard-things - **The Gatekeepers** — Chris Whipple THE book for Chiefs of Staff - the origin and lessons on crisis management and leadership. Explains the reasons why Chiefs of Staff exist in the first place. https://www.goodreads.com/book/show/31159759-the-gatekeepers - **Americana** — Bhu Srinivasan What an engaging view of American exceptionalism told through the history of innovation, economic shifts and development of commerce as we know it. https://www.goodreads.com/book/show/34272478-americana - **Skin in the Game** — Nassim Nicholas Taleb Provides lenses through which to view risk and accountability. A great tutorial on how to judge people (including myself) by what they risk, not what they say. https://www.goodreads.com/book/show/36064445-skin-in-the-game - **Zero to One** — Peter Thiel We aren't building monopolies, but first principles and critical thinking, challenging conventional wisdom is a virtue to learn and practice. https://www.goodreads.com/book/show/18050143-zero-to-one - **One Second After** — William R. Forstchen Makes you think just how fragile our civilization is and how dependent it is on the current tech stack. https://www.goodreads.com/book/show/4922079-one-second-after - **Several Short Sentences About Writing** — Verlyn Klinkenborg Writing is thinking. Cutting academic fluff and bad habits from writing makes it clearer, adding rhythm and trust to one's thoughts. Worth a refresh. https://www.goodreads.com/book/show/13155290-several-short-sentences-about-writing - **Animal Farm** — George Orwell Parallelism to reality aside, it's worth a re-read every time. Smartly written. https://www.goodreads.com/book/show/170448.Animal_Farm - **Heavy Weather Sailing** — Martin Thomas Fantastic guide on how not to die at sea, which is always worth the read time before ocean crossing. https://www.goodreads.com/book/show/63257208-heavy-weather-sailing-8th-edition - **Sapiens** — Yuval Noah Harari Worth knowing where we all came from and how we use shared myths, like money and laws, to live together. https://www.goodreads.com/book/show/23692271-sapiens ## Contact If you're building, investing, or just curious about early-stage companies, AI, or the work behind execution — [reach out](mailto:dmitri.erchov@gmail.com). Equally happy to talk about offshore sailing.