Chief Technology Officer

Who we are

The Outreach Team is the national engine of campaigners and organizers helping causes win victories, hearts, and minds on the ground. We run field programs — voter contact, organizing, voter registration, signature gathering and ballot initiatives, and face-to-face fundraising — for campaigns and causes across the country, hiring locally and operating with the integrity it takes to win. In a big election year, we put thousands of staff on doors for well over a hundred clients.

We believe meaningful change begins with authentic human connection. Technology cannot replace the conversation at the door, but it can empower the people having those conversations. Our role is to build systems that help our staff reach more communities, make better-informed decisions, and ensure the operational foundations, from data to payroll, are reliable, accurate, and scalable. 

This Role Will Evolve

As our first Chief Technology Officer, your initial priorities will be highly operational. You'll spend your first year improving internal systems, data, security, and business operations while building the technology function from the ground up. Over time, the role will expand beyond operational leadership to include technology strategy, product innovation, and organizational growth.

We are a company built on human judgment and hand-tooled systems: a data warehouse and dashboards our field leaders actually use, a recruiting operation and payroll customization ahead of other programs. The people who built all of that built a company that works but with tools chosen for a company half our current size. We don't need a visionary to sprinkle AI on top of what our company already has. We need a builder to put the right foundations under a growing business. The differentiating layer—the analytics our clients will buy and the field intelligence our on-the-ground teams need—will be built on those foundations. You'll build cool new stuff, too, but the foundations come first. 

You will report to our CEO, sit with the executive team, and carry a mandate leadership has already aligned on. The three-year contract is by design: long enough to build the platform and run a presidential cycle on it, and honest that what the company needs afterward — a permanent CTO, a technology director or IT director you have trained, or something else — is a question you will help answer.

What you’ll own

»    A system of record. Move the company’s core loops — budget-versus-actual, campaign launch, policy changes, decisions made on calls — out of inboxes and Slack threads and into systems, whether that means an ERP, targeted platforms, or something we build. The principle: work flows through systems rather than correspondence. This is your first deliverable.

»  The employment pipeline, end to end. Evaluate and revamp the system that takes a canvasser from application through onboarding, scheduling, hours, pay, final pay, and offboarding into an alumni network — with multi-state wage-and-hour compliance built in. We pay thousands of people weekly across numerous pay policies and it needs to be seamless. 

»    Our data. Evaluate the company owned subscriptions and data pipelines, then lead the analytics and qualitative-insight product-building.

»    Security and AI governance. Bring device management, access control, and vendor security to a fully remote workforce; answer client security questionnaires; write and enforce a company AI policy.

»    The technology team. Grow our BI and systems group: queue transparency, real training budgets, documentation, and successors, so no critical system depends on exactly one person’s memory.

Your first year

You'll arrive in 2026 as a major election cycle spins up and then winds down. Use it to understand how the organization operates under real campaign conditions. Over the winter, you’ll map the systems, run audits, and then bring the executive team an architecture and a roadmap of what we buy versus what we build, and what it costs. 2027 is the build year with migrations, pilots in live offices, and foundation-building. In 2028, we run a presidential-scale cycle on the new foundation. 

Who you are

»    You have owned technology for an operating business at real scale — a company with a distributed, hourly frontline workforce: staffing, logistics, field services, multi-site healthcare, or campaigns. Political experience is welcome and not required; the ability to learn this business fast is required.

»    You think about frontline users the way Apple thinks about its customers. Our field directors are your users. If a tool adds a minute to their day at peak, you count it as a cost.

»    You have buy-build-adapt judgment and the scar tissue to prove it: an ERP or system-of-record implementation you’ve led, vendor selections that went well and badly, an integration you regret and can autopsy without blaming the users.

»    You treat compliance as part of the architecture. Multi-state wage-and-hour exposure doesn’t scare you.

»    You build successors. You document, you train, and you make yourself less necessary. This is a three-year contract, and part of the job is working with us to decide what comes after you. 

»    You respect what you inherit. The people here built a company that works. If your first instinct when you encounter a hand-built system is to dismiss it rather than understand it, this isn't the job for you. 

Compensation, term, and logistics

Salary of $200,000-$225,000, commensurate with experience, on a three-year initial contract. We offer benefits including fully paid health care, vacation and sick days. Remote from anywhere in the U.S., with regular monthly travel to field offices and leadership convenings. A mandate with genuine authority.

How to apply:  https://www.theoutreachteam.net/jobs