Remote Chief Engineer Jobs in Illinois (NOW HIRING)

About Caribou
At Caribou, we care about giving people financial freedom so they can focus on what's most important to them. Today, less than two percent of Americans refinance their auto loans despite drastic increases in the cost of new and used cars. We see huge potential to help folks reduce their monthly auto expenses, as well as increase the predictability of those expenses over time. We do this by building technology to pair customers with community banks and credit unions, and ushering them through the process quickly. On average, our drivers save $162/month on their car loans while protecting their investment long term.
Caribou is led by leaders from the technology, automotive, and finance industries. We're proud to be backed by a great team of investors, including QED Investors, Goldman Sachs, Moderne Ventures, Accomplice, Link Ventures, Motley Fool Ventures and others.
About the role
You'll be the sole people manager for an established team of 10 solid engineers (6 onshore, 4 nearshore) building the LOS/CRM platform behind our refinance process. The team is more than a third of Caribou's product engineering, and you'll be one of six leaders reporting to the CTO.
The team operates in a Ruby on Rails monolith and a Python monorepo for Google ADK Agents. The strategic mandate for the role is to build agentic orchestration to guide our origination platform, automating the repetitive, high-volume steps of the refinance process so our team can spend more time on the applications and moments that need a person's judgment.
Round-the-clock agentic orchestration extends what our team can already do by handling routine steps at any hour so customers get faster answers, while our team focuses on the applications where a person makes the difference.
Separate from the product work, we're deploying agentic engineering across all repos using Claude Code. You'll improve your team's practice across practitioner capability and codebase readiness, targeting top-quintile productivity and helping define how we measure it.
The team is new to agentic orchestration, and bringing them up on it is the work. Within the year, we expect agentic orchestration to be handling the full range of routine refi steps, with our team focused on exceptions, edge cases, and judgment calls. Your management and architecture skills sharpen on the way, and scope grows as you prove it out.
What you'll do

• Build and hold the team: hiring, coaching, performance conversations, and career growth for ten engineers.
• You won't ship features. You will read designs, weigh trade-offs with senior engineers, and know how the system actually works.
• Keep the codebase healthy across quarters, including making the case to Product when tech debt needs paying down.
• Grow your team's agentic engineering practice, moving each engineer up our capability model through mentoring and pairing.
• Lead production health for your team's services: on-call rotation, alerts and monitoring, incident response, and the follow-through after.
• Guide secure SDLC for your team: vulnerability patching, threat modeling on new agentic surfaces, and origination workflows kept audit-ready under SOC 2 and GLBA.
• Partner with Product, design, security, and data. Product sets the roadmap. You decide how it gets built.
• Collaborate with the other engineering managers to set how we engineer at Caribou.

What we look for:

• Prior experience leading engineers who build and operate production applications and back-end integrations.
• Experience guiding a team's shift to agentic engineering, or adding AI into existing products for material business value.
• Customer-focused leaders with a passion for well-crafted software, committed to growing their own leadership and engineering skills.
• Experience leading a distributed team across time zones, including nearshore or offshore engineers.
• Full-stack understanding of production software systems, from hosts and HTML, to models and MCP, to databases and DNS, to runtimes and REST.
• Collaborative, people-first leaders who lead with context over command and control.

If you meet most of what's above and not all of it, apply anyway.
We value diverse paths into engineering leadership. Consulting backgrounds, career changers, and candidates without four-year degrees have succeeded here, and we're actively building a team that reflects the communities we serve. Tell us what you've built.
Caribou is committed to providing reasonable accommodations throughout the hiring process. If you need an accommodation, let us know.
Locations
Candidates are welcome to work remotely from the states of AZ, CO, DC, IL, MD, TX, and VA with a preference for the Chicago IL, Denver CO, or Phoenix AZ areas. Caribou does provide the option to work in-office or hybrid from our Denver, CO or Chandler, AZ offices. We may consider remote candidates in CA, FL, MA, NY, OR, WA, and WI, subject to additional approval. Eligibility by state is subject to change.
Interview Roadmap:

• Recruiter phone interview (45 mins)
• At-home technical assessment (60 mins)
• Hiring Manager interview (60 mins)
• Final interview loop (combined 4 hrs scheduled across 1-4 business days)

How we will take care of you
Everyone at Caribou is a valued team member. Our compensation and benefits package includes:

• Competitive compensation: $174,000 - $217,000
• Equity options
• 401k savings program
• Generous paid time off including Flexible Time Off (FTO) for all employees and 100% paid parental leave for all parents
• Company-paid plans for health, dental, vision, mental health, disability, and basic life insurance
• Optional benefits to suit your individual circumstances such as HSAs, FSAs, supplemental life and medical insurance, and pet insurance
• Up to $1,000 per year for eligible professional development expenses

Our Core Values
We come from all walks of life and are joined together by our shared values, which guide our work and how we work together.

• Give a damn. What we're doing matters. We show up determined to deliver results, and we love it.
• Velocity. We're intentional about where we're going and we race towards it.
• Make the assist. We have diverse strengths. We offer and ask for help so we all win.

The essential functions of this position require consistent attendance, availability, and active engagement throughout your full scheduled shift.
Caribou is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, age, disability, sexual orientation, pregnancy status, marital status, military or protected veteran status, genetics, or any other characteristic protected by law. This position is not restricted solely to the responsibilities listed above, and the scope and responsibilities are subject to change. A pre-employment background check is required as a condition of employment.
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