Applied AI Strategist

Regen8; Bend (OR); On-site; USD 120,000 - 170,000; Full time

Job summary

Regen8 in Bend, Oregon partners with mid-market teams to deploy AI operating systems that keep workloads and data under client control. This role is client-facing, shaping engagements from initial talks to production-ready agents without writing code.

You’ll assess processes, build compelling business cases, and guide engineers on how to scale solutions while maintaining human oversight and governance across deployments.

Qualifications

• Excellent written and verbal communication with stakeholders.
• Ability to map complex processes into actionable briefs.
• Experience reasoning about business value and adoption.

Responsibilities

• Run Sprint Zero with stakeholder interviews, process mapping, and executive readouts.
• Identify the top operation to rebuild and defend its value.
• Build the business case, size opportunity, model value, compare estimates vs. measurements.
• Define proof criteria and baseline before go-live.
• Turn ambiguous problems into agent briefs with success criteria and guardrails.
• Design work division between people and agents, preserving human decision authority.
• Drive adoption and change management, train users, gather feedback.
• Tell the story of changes after deployment, including unmet expectations.
• Find next operation to do inside existing client base.

Skills

Communication

Analytical thinking

Commercial judgment

AI fluency

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

Applied AI Strategists are the client-facing operators. You own the engagement from the first conversation to the agent running in production, paired with a Forward-Deployed Engineer who owns the architecture and the build.

This is a role for people who communicate clearly, think like operators, and reason like investors. You sit across from an owner and a bookkeeper in the same week, map how the process actually runs, and turn that into a business case and a brief an engineer can build against. You do not write the code. You decide what gets built, what it is worth, and how it gets adopted.

The role starts on contract and converts to full-time on performance, which is when equity and bonus come with it. We would rather prove the fit on real client work than on an interview loop.

You will learn AI here by doing it. You will scope agents yourself, work beside the engineers on live deployments, and use the same toolkit we use to run the company. Reading about agents and carrying one inside someone's business are different jobs. This is the second one.

What you will do

• Run Sprint Zero: stakeholder interviews, process mapping, hypothesis-driven analysis, and an executive readout that survives questioning
• Find the one operation worth rebuilding first, and be able to defend why it beats the other nine
• Build the business case. Size the opportunity, model the value, and say out loud what you are estimating versus what you have measured
• Define what will count as proof before anything is built, and baseline it before go-live
• Turn ambiguous problems into agent briefs with success criteria, guardrails, and a definition of done an engineer can build against
• Design the division of work between people and agents, and where decision authority stays human
• Drive adoption and change management. Train the team, sit with the users, and feed what you see into the next iteration
• Own the story of what actually changed after deployment, including when the honest answer is less than we hoped
• Find the next operation worth doing inside clients we already serve

What we are looking for

Three skillsets that are rare in one person: communication, analysis, and commercial judgment. You need to be strong in all three.

• Track record You have solved ambiguous problems for senior stakeholders and seen the result through, whether as a consultant, an investor, an operator, a business operations lead, or a founder.
• Client presence You can hold a room, push back on an owner without losing them, and tailor depth to the audience.
• Analytical rigor You can model a business, pressure-test a number, and pick up an unfamiliar industry almost instantly.
• Commercial sense You understand where the value is, who is paying for it, and what a good engagement looks like from the client’s side.
• AI fluency You use AI tools daily, you hold a view on where agents work and where they do not, and you can brief an engineer precisely.
• Honesty about numbers You are specific, and you say plainly when you do not have one. We publish estimates labelled as estimates, and this role holds that line.

Helpful experience

• Deployment strategist or engagement lead at an AI company
• Strategy consulting with an operations or AI focus
• Private equity or investment banking, especially anyone who has sat on the operating side of a portfolio company
• Business operations, chief of staff, or corporate strategy at a high-growth company
• Operations leadership inside a mid-market business, particularly finance, revenue operations, or supply chain
• Founder or early employee at a company that sold into business buyers