📌 Core Information
🔹 Job Title: Head of Marketplace Automation & Growth
🔹 Company: Jerry.ai
🔹 Location: San Francisco Bay Area, California, United States (Remote OK)
🔹 Job Type: Full-Time
🔹 Category: Insurance, Fintech
🔹 Date Posted: 2025-07-30
🔹 Experience Level: 5-10 years
🔹 Remote Status: Remote OK
🚀 Job Overview
Key aspects of this role include:
- Scaling Jerry's core insurance business through marketplace automation and growth strategies
- Cross-functional collaboration with product, engineering, and analytics teams to create seamless user experiences
- Ensuring ongoing carrier success and driving critical outcomes for Jerry's insurance marketplace
- Working closely with brilliant leaders and teammates from top-tier companies
ASSUMPTION: This role requires a high level of strategic thinking, problem-solving, and cross-functional collaboration to drive growth and improve user experiences in Jerry's insurance marketplace.
📋 Key Responsibilities
✅ Own and drive the systems, strategy, and execution behind Jerry’s quoting engine, automation infrastructure, and carrier performance
✅ Collaborate cross-functionally with product, engineering, and analytics teams to create a seamless user experience and ensure ongoing carrier success
✅ Achieve critical outcomes for Jerry’s insurance marketplace, including loss ratio, retention, and conversion
✅ Hire, manage, and mentor a high-performing team to support marketplace automation and growth efforts
ASSUMPTION: This role involves a high degree of ownership, strategic decision-making, and team management to achieve Jerry's ambitious growth goals.
🎯 Required Qualifications
Education: Bachelor’s degree in a quantitative discipline (e.g., Electrical Engineering, Computer Engineering, Industrial Engineering, Operations Research)
Experience: 7+ years of management consulting experience from a top firm (McKinsey, Bain, Boston Consulting Group preferred)
Required Skills:
- Proven track record of hiring and managing high-performing teams
- Structured problem-solving framework and first principles thinking
- Excellent communication skills with various stakeholders, including technical teams and C-suite executives
- Strong cross-functional collaboration and project management skills
- Experience with insurance operations, quoting engines, automation infrastructure, and carrier performance
Preferred Skills:
- Experience with AI, machine learning, and data analysis
- Background in user experience design or optimization
- Familiarity with the insurance industry and market trends
ASSUMPTION: Candidates with a strong quantitative background, proven management consulting experience, and a track record of driving growth and improving user experiences will be most successful in this role.
💰 Compensation & Benefits
Salary Range: $180,000 - $250,000 per year (AI-estimated, based on role, experience level, and location)
Benefits:
- Health, dental, and vision insurance
- 401(k) plan with company match
- Unlimited PTO and flexible work arrangements
- Equity compensation
- Professional development opportunities
Working Hours: Full-time (40 hours/week), with flexible work arrangements
ASSUMPTION: The provided salary range is an estimate based on market data for similar roles, experience levels, and locations. Actual compensation may vary based on factors such as skills, qualifications, and company performance.
📌 Applicant Insights
🔍 Company Context
Industry: Fintech, Insurance
Company Size: 201-500 employees (Mid-size)
Founded: 2017
Company Description:
- Jerry.ai is America’s first and only super app to radically simplify car ownership
- Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs
- Jerry.ai is the #1 rated and most downloaded app in its category with a 4.7 star rating in the App Store, serving over 5 million customers
Company Specialties:
- Insurance
- Artificial Intelligence
- Mobile Application
- Consumer Software
- Internet Technology
- Fintech
- Automotive
- Insurtech
Company Website: jerry.ai
ASSUMPTION: Jerry.ai is a fast-growing, innovative fintech company focused on disrupting the car ownership market through AI-powered solutions and exceptional user experiences.
📊 Role Analysis
Career Level: Senior Management
Reporting Structure: Reports directly to the VP of Insurance Operations
Work Arrangement: Remote OK, with flexible work arrangements
Growth Opportunities:
- Potential to grow into a VP or C-level role as the company expands
- Opportunities to lead and mentor teams, driving career development for team members
- Exposure to various aspects of the business, fostering a well-rounded skill set
ASSUMPTION: This role offers significant growth potential as Jerry.ai continues to scale and expand its offerings.
🌍 Location & Work Environment
Office Type: Remote-first, with physical offices in Palo Alto, CA; Toronto, ON; and Lockport, NY
Office Location(s): San Francisco Bay Area, California, United States (Remote OK)
Geographic Context:
- The San Francisco Bay Area is a major tech hub with a vibrant job market and diverse cultural scene
- Remote work allows for flexibility and work-life balance
- Jerry.ai's remote-friendly culture fosters collaboration and inclusivity among team members
Work Schedule: Full-time (40 hours/week), with flexible work arrangements
ASSUMPTION: The remote-friendly work environment at Jerry.ai promotes flexibility, work-life balance, and collaboration among team members.
💼 Interview & Application Insights
Typical Process:
- Phone or video screen with a member of the HR team
- Behavioral and technical interviews with cross-functional team members
- Final interview with the VP of Insurance Operations
- Background check and reference check
Key Assessment Areas:
- Problem-solving skills and strategic thinking
- Cross-functional collaboration and communication
- Leadership and team management abilities
- Industry knowledge and market trends
Application Tips:
- Tailor your resume and cover letter to highlight your quantitative background, management consulting experience, and relevant skills
- Prepare for behavioral and technical interview questions that focus on your problem-solving, leadership, and cross-functional collaboration skills
- Research Jerry.ai's mission, values, and company culture to demonstrate your fit and enthusiasm for the role
ATS Keywords: Marketplace Automation, Growth Strategy, Team Management, Problem Solving, Communication, Cross-Functional Collaboration, User Experience, Insurance Operations, Data Analysis, AI, Machine Learning, Customer Retention, Conversion Optimization, Carrier Performance, Quoting Engine, Automation Infrastructure
ASSUMPTION: The interview process at Jerry.ai focuses on assessing candidates' problem-solving, leadership, and cross-functional collaboration skills, as well as their cultural fit with the company's mission and values.
🛠️ Tools & Technologies
- AI and machine learning platforms
- Data analysis and visualization tools
- Project management and collaboration software
- Insurance industry-specific software and systems
ASSUMPTION: The specific tools and technologies used in this role may vary depending on the candidate's background and the team's needs, but a strong foundation in AI, machine learning, and data analysis is essential.
👔 Cultural Fit Considerations
Company Values:
- Customer-centric
- Innovative
- Data-driven
- Collaborative
- Accountable
Work Style:
- Fast-paced and dynamic
- Cross-functional and collaborative
- Data-driven and analytical
- Results-oriented and accountable
Self-Assessment Questions:
- Do you thrive in a fast-paced, dynamic environment, and are you comfortable working with various stakeholders to drive growth and improve user experiences?
- Are you a strong communicator with excellent written, verbal, and presentation skills?
- Do you have a structured problem-solving framework and a data-driven approach to decision-making?
ASSUMPTION: Candidates who are customer-centric, innovative, data-driven, collaborative, and accountable will be most successful at Jerry.ai.
⚠️ Potential Challenges
- Managing and scaling a high-performing team in a fast-growing, dynamic environment
- Balancing strategic decision-making with day-to-day tactical execution
- Navigating a complex, multi-stakeholder environment to drive growth and improve user experiences
- Keeping up with industry trends and market changes to maintain a competitive edge
ASSUMPTION: This role presents unique challenges and opportunities for growth, requiring a strong, adaptable leader with a proven track record of driving results in dynamic environments.
📈 Similar Roles Comparison
- Unlike traditional insurance roles, this position focuses on marketplace automation and growth strategies, requiring a unique blend of skills and experience
- Jerry.ai's innovative, customer-centric approach to car ownership sets it apart from traditional insurance companies and fintech competitors
- This role offers significant growth potential as Jerry.ai continues to expand its offerings and enter new markets
ASSUMPTION: This role is unique in its focus on marketplace automation and growth strategies, requiring a strong, adaptable leader with a proven track record of driving results in dynamic environments.
📝 Sample Projects
- Developing and implementing a comprehensive quoting engine optimization strategy to improve conversion rates and reduce loss ratios
- Designing and executing a data-driven customer retention campaign to increase customer lifetime value and reduce churn
- Collaborating with cross-functional teams to launch a new insurance product or feature, driving user adoption and market penetration
ASSUMPION: These sample projects illustrate the strategic, cross-functional nature of the Head of Marketplace Automation & Growth role at Jerry.ai.
❓ Key Questions to Ask During Interview
- How does Jerry.ai differentiate itself from traditional insurance companies and fintech competitors in the marketplace automation and growth space?
- What are the key priorities for this role in the first 30, 60, and 90 days?
- How does Jerry.ai support the professional development and growth of its employees?
- What are the biggest challenges facing Jerry.ai in the next 12-24 months, and how can this role help address them?
- How does Jerry.ai foster a culture of innovation, collaboration, and accountability among its team members?
ASSUMPTION: These key questions help candidates better understand the role, the company's priorities, and the cultural fit between the candidate and Jerry.ai.
📌 Next Steps for Applicants
To apply for this position:
- Submit your application through this link
- Tailor your resume and cover letter to highlight your quantitative background, management consulting experience, and relevant skills
- Prepare for behavioral and technical interview questions that focus on your problem-solving, leadership, and cross-functional collaboration skills
- Research Jerry.ai's mission, values, and company culture to demonstrate your fit and enthusiasm for the role
- Follow up with the hiring manager one week after submitting your application to express your interest and reiterate your qualifications
⚠️ This job description contains AI-assisted information. Details should be verified directly with the employer before making decisions.
