Job Description

Our Client is looking for a hands-on Head of Operations & Automation to help them strengthen the systems, workflows, and automations that support their next stage of growth.

Our Client is the company behind a powerful and flexible operating system used by a deeply engaged global community since 2005. As their product, partnerships, infrastructure, and internal operations continue to evolve, they are looking for someone who can help design the operational systems that keep work moving clearly across teams.

This role sits at the intersection of business operations, product and engineering coordination, AI-enabled automation, and cross-functional communication. You’ll help them build practical systems that create clarity, predictable deterministic outcomes, reduce manual coordination, and allow department leaders to stay focused on their highest-value work.

This is a builder role for someone who leads with understanding. Before designing anything, you need to see the full picture: how their team works together, the history behind their current systems, the relationships between departments, and the small details that only surface when you take the time to listen. From the big picture down to the nuances. They're a tight, long-tenured, high-performing team, and they're not looking for someone who shows up with a playbook and expects the team to conform. They need someone who respects what's been built while designing what comes next.

Success in this role will look like

• Cross-functional projects have clear visibility on: owners, next steps, blockers, and status

• Releases are coordinated smoothly across Product, Engineering, QA, Support, Marketing, Partnerships, and Documentation

• Department heads spend less time chasing updates and more time leading their areas of expertise

• Product and engineering operations are easier to understand and maintain

• AI agents and automations reduce manual coordination work

• Internal documentation stays useful, current, and actionable

• New hires and contractors ramp more efficiently, with less institutional knowledge transfer required due to strategically designed operational systems

• The team has fewer “where does this stand?” moments because the systems already provide that visibility

Responsibilities

Cross-Functional Operations

You will help design and improve the operating rhythms that connect Product, Engineering, Quality, Marketing, Support, Partnerships, and IT/DevOps. This includes:

• Designing clear intake processes for requests, projects, and cross-functional initiatives

• Creating repeatable handoff systems between departments

• Improving release readiness and launch coordination

• Helping define ownership, next steps, blockers, and communication pathways for active projects

• Supporting retrospectives and follow-through after major releases, projects, or operational changes

• Creating documentation that helps a remote team operate with less reliance on verbal handoff

Product & Engineering Operations

Your early focus will be heavily weighted toward Product and Engineering operations. In the first 90 days, you’ll partner closely with the Director of Product to strengthen how product and engineering work is tracked, connected, and communicated across the company. This includes:

• Improving the way their internal communication and work systems connect

• Creating clearer visibility into project status, blockers, and release readiness

• Supporting product and engineering operating cadences

• Helping ensure Support, Marketing, Partnerships, and Documentation have the information they need before launches

• Building systems that allow technical work to translate into clear cross-functional updates

• The goal is not simply to add more processes. The goal is to create lightweight, useful systems that make work easier to understand, easier to move forward, and easier to communicate.

AI Tooling & Operational Strategy

You will also help our Client develop a thoughtful internal approach to AI tooling. This includes:

• Evaluating and recommending AI tools

• Helping consolidate overlapping tools or workflows

• Supporting internal guidelines for responsible AI use

• Helping department heads identify practical, high-ROI AI use cases

• Building repeatable patterns so AI adoption does not depend on each department figuring it out alone

AI Automation & Internal Tools

A key part of this role is identifying where AI and automation can reduce repetitive coordination work. You will build or support tools such as:

• AI-assisted release note drafting

• Daily or weekly project status summaries from tools like Linear, GitHub, or Asana

• Meeting-to-action-item workflows

• Partner or support request triage

• Internal tools that surface blockers, patterns, or follow-up items

• Agents that help teams stay aligned without adding more meetings

They are looking for someone who is comfortable operating in the technical space as outlined in the section “What ‘Technical’ Means in this Role”.

What “Technical” Means in This Role

Technical means that you can engage credibly with product and engineering teams while also building practical internal systems yourself.

You should have experience with some combination of:

• Writing in TypeScript or Python

• Working with APIs, webhooks, and system integrations

• Building or prototyping AI-powered workflows using tools like Claude, OpenAI, or similar platforms

• Comfort with cloud infrastructure like Cloudflare Workers to enable deployment of your tools to run on hosted infrastructure, rather than on your local machine

• Reading technical documentation and translating it into working systems

• Understanding software development workflows, including tickets, pull requests, QA, release cycles, and product feedback loops

• Communicating technical context clearly to non-technical stakeholders

You do not need to be a full-stack software engineer. You do need to be technical enough that you need very little to no assistance with your integration work.

Requirements

This role sits at the intersection of technical depth, operational instincts, and people skills. They need someone who can build an automated workflow in the morning, redesign a cross-functional process in the afternoon, and navigate a sensitive conversation with a long-tenured team member with the same level of care. None of these three skillsets is optional. The technical credibility earns you trust with engineering. The operational thinking creates the systems that make everyone's work easier. And the people skills are what make any of it actually stick in a team like theirs.

• 5+ years of experience in technical program management, product operations, engineering operations, business operations, automation, or a similar cross-functional role

• Experience working inside a software product company

• Experience working remotely

• Hands-on technical ability with scripting, APIs, automations, or AI-assisted workflows

• Experience building or implementing internal tools, automations, or LLM-based workflows

• Strong written communication skills, especially in a remote environment

• Ability to create clarity across multiple workstreams without adding unnecessary bureaucracy

• Sound judgment about when to escalate, when to solve directly, and when to simplify

• A bias toward follow-through, documentation, and closing loops

• Comfort working in a small company where people wear multiple hats

• Enthusiasm for joining a small team entering its next stage of growth and helping build the systems that make that growth possible

• Possess an active Visa for an in-person interview in the USA if needed

Nice to Have

• Experience at a small or scaling software company

• Experience working in a fully remote company

• Experience with product-led, community-driven, open-source, developer-focused, or infrastructure-adjacent products

• Familiarity with Unraid, Docker, virtualization, NAS, Linux, homelab communities, or enthusiast technical communities

• Experience introducing operating cadences, project health reporting, retrospectives, or release workflows

• Experience helping teams adopt AI tools in a thoughtful and responsible way

* This position is hybrid