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Director, Monetization Strategy and Operations

Chicago, IL | Denver, CO | Phoenix, AZ | Remote, US
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 $115/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

Caribou is looking for a Director, Monetization Strategy and Operations to own and grow one of Caribou’s most critical revenue streams. This Director-level role carries full P&L responsibility across consumer and lender fees, discounting strategy, vehicle protection products (e.g., warranties, vehicle service contracts, GAP), and future ancillary revenue opportunities like insurance, data, and advertising.

This is a high-impact, individual contributor role. You’ll lead outcomes—not people—by influencing across functions, building strong partnerships, and driving strategy from concept to execution. You’ll work directly with leaders in Sales, Product, Finance, Legal, and Operations to deliver results.

In this role, you will…

Own Strategy and Outcomes

  • Lead monetization strategy across:
    • Vehicle protection products (e.g., warranties, vehicle service contracts, GAP)
    • Lender fees
    • Product Pricing
    • Future cross-sell opportunities (e.g., insurance, data products, advertising)
  • Define what we offer, to whom, and at what price—across digital and contact center channels
  • Develop and own P&L models, unit economics, and pricing strategy to drive sustainable revenue growth

Manage Vendors and Monetization Partnerships

  • Own relationships and outcomes with F&I product providers and monetization partners
  • Structure and negotiate vendor contracts, underwriting terms, and revenue share agreements
  • Evaluate and onboard new partners aligned with our product, risk, and revenue goals

Drive Cross-functional Execution

  • Collaborate with Sales to design pitches, training, workflows, and compliance adherence
  • Work with Product and Engineering to define and prioritize tooling and consumer experience enhancements
  • Align with Finance, Legal, and Ops to execute programs effectively and monitor impact

What does success look like?

  • Product Margin per Loan: $ profit per funded loan
  • Total Monetization Revenue and Profitability
  • Customer Satisfaction/NPS (as impacted by monetization experience)

Future Growth Opportunity

This role is core to Caribou’s long-term strategy. With strong execution and measurable impact, the Director, Monetization Strategy and Operations may expand into broader strategic initiatives—including launching new monetization channels, leading cross-functional growth programs, or taking on additional commercial scope. It’s a rare opportunity for a business athlete to lead from the front and scale with the company.

Location

This role can be based out of one of our Caribou offices in Denver, CO or Chandler, AZ. Alternatively, this role may work remotely from a state where Caribou operates with a preference for the Chicago, IL, or Washington, DC metro areas.*  This role requires attendance at occasional in-person team meetings. 

About You

You, like us, are driven to achieve your goals. At Caribou, we have just three core values: Give a damn. Velocity. Make the assist. We’re motivated. We race towards our goals. And we help each other along the way. 

  • 8+ years of experience in monetization, business strategy, consumer lending
  • Experience working with ancillary F&I products in the Automotive space is a major plus
  • Strong operator with a proven ability to lead high-impact initiatives as an individual contributor
  • Deep experience in pricing, financial modeling, vendor negotiation, relationship management, and margin optimization
  • Cross-functional influence and ability to drive outcomes across Sales, Product, and Finance
  • Experience in lending, fintech, insurance, or marketplaces is a plus

How we will take care of you

Everyone at Caribou is a valued team member. Our compensation and benefits package includes: 

  • Competitive compensation: $150k-$185k
  • Eligible for annual performance based bonus 
  • 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.
  • Robust wellness benefits including 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.  

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.

*Caribou does not currently have employee operations in AL, AK, AR, CT, DE, GA, HI, IA, ID, IN, KS, KY, ME, MI, MS, MT, NC, ND, NE, NH, NJ, NM, NV, OH, OK, PA, RI, SC, SD, TN, UT, VT, WV, WY.

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