Director - Monetization Strategy and Operations
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.
About the job
Apply for this position
Director - Monetization Strategy and Operations
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.