Head of Operations

Regen8; Bend (OR); On-site; USD 90,000 - 150,000; Full time

Job summary

Regen8 builds AI operating systems for mid-market companies. We embed with operators, map how work moves, and deploy the first agent into governed production in 30 days. The role starts as a fractional engagement with a path to full-time and equity as the business grows.

You own delivery across live engagements and the commercial back office, and you automate your own job as you go. This is not a fit for someone seeking a narrow scope or predictable week.

Qualifications

• Operational experience running a services or delivery business with profitability responsibility.
• Ability to build automation end-to-end using tools like n8n.
• Ability to give early warnings when dates will not be met.
• Focus on creating repeatable processes rather than heroic last-minute fixes.
• Comfort with ambiguity and being the sole person in the function.

Responsibilities

• Own delivery across live engagements: people, milestones, and risks.
• Build our internal operating system with client tooling in mind.
• Own the commercial back office: proposals, contracts, invoicing, and metrics.
• Turn each engagement into reusable methods to reduce future costs.
• Maintain evidence: track what is measured, estimated, and public claims.
• Develop hiring and onboarding processes as the team grows.

Skills

Operating experience

Builder, not specifier

Early warnings

Systems over heroics

Comfort with ambiguity

n8n automation

Tools

n8n

Language model in the loop

Job description

Regen8 builds AI operating systems for mid-market companies. We build for sovereignty: the client’s workloads, their data, and the intelligence the system accumulates stay theirs. Our forward-deployed teams embed with operators, map how the work actually moves, and put the first agent into governed production in 30 days.

We work where trust shapes how work gets done: private equity and their portfolio companies, digital health, manufacturing, and construction. In these businesses, judgment and accountability are not tradeable for speed. Three rules hold on every build. Systems of record remain authoritative. Human authority remains explicit. Context, controls, and learning stay with the client.

About the role

You make Regen8 run the way we tell clients to run. We sell AI operating systems, so we are our own first client, and how we operate is part of the evidence we put in front of buyers.

This starts as a fractional engagement, with a path to full-time and equity as the business carries it. You own delivery across live engagements and the commercial back office behind them, hands-on , with no team under you. You will do the work before you manage it, and you will automate your own job as you go. A fractional operator who builds the system is worth more to us than a full-time one who runs it manually.

This is probably not the right fit if you want a narrow scope or a predictable week.

What you will do

• Own delivery across live engagements: who is on what, what is slipping, and what is about to
• Build our internal operating system with the same tools we deploy for clients. If we are telling a client to automate their invoicing, ours should already be automated
• Own the commercial back office: proposals, contracts, invoicing, and the numbers that say whether an engagement was worth running
• Turn each engagement into reusable method, so the second build costs less than the first
• Keep the evidence straight. Which claims are measured, which are estimates, and what we are allowed to say publicly about which client
• Build the hiring and onboarding process as the team grows, and hold the standard while it changes

What we are looking for

• Operating experience You have run operations at a services or delivery business and carried responsibility for whether it made money.
• Builder, not specifier Fluent enough with automation to build it yourself. You should be comfortable in something like n8n, and comfortable with a language model in the loop.
• Early warnings You are the person who says a date will not be met, early, to the people who do not want to hear it.
• Systems over heroics The job is making the second time easier.
• Comfort with ambiguity And with being the only person in your function.

Helpful experience

• Operations or delivery lead at a consultancy, agency, or professional services firm
• Chief of staff or business operations at a high-growth company
• Finance or revenue operations leadership in the mid-market
• Founder or early operator who has built the back office from nothing
• Fractional operator who has carried more than one company at a time