📌 Core Information
🔹 Job Title: Head of Marketplace Automation & Growth
🔹 Company: Jerry
🔹 Location: San Francisco Bay Area, California, United States (Remote OK)
🔹 Job Type: Full-Time
🔹 Category: Software Development
🔹 Date Posted: 2025-07-18
🔹 Experience Level: 5-10 years
🔹 Remote Status: Remote OK
🚀 Job Overview
Key aspects of this role include:
- Scaling Jerry's core insurance business
- Owning and driving the strategy behind Jerry’s quoting engine and automation infrastructure
- Cross-functional collaboration with product, engineering, and analytics teams
- Ensuring ongoing carrier success and driving critical outcomes for the insurance marketplace
ASSUMPTION: This role requires a strategic mindset, strong analytical skills, and the ability to work effectively with various teams to achieve business goals.
📋 Key Responsibilities
✅ Own and drive the systems, strategy, and execution behind Jerry’s quoting engine and automation infrastructure
✅ Collaborate cross-functionally with product, engineering, and analytics teams to create a seamless user experience
✅ Ensure ongoing carrier success and drive critical outcomes for the insurance marketplace (loss ratio, retention, and conversion)
✅ Report directly to the VP of Insurance Operations and work closely with other leaders to achieve business objectives
ASSUMPTION: This role involves a high level of autonomy and requires strong leadership, decision-making, and communication skills.
🎯 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, and 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 analytical skills and data-driven decision-making
- Proven ability to set high standards and continuously push for excellence
Preferred Skills:
- Experience in the insurance or fintech industry
- Familiarity with AI and machine learning technologies
ASSUMPTION: Candidates with a strong background in management consulting and a proven track record in leadership roles are likely to succeed in this position.
💰 Compensation & Benefits
Salary Range: $150,000 - $250,000 per year (Based on industry standards for similar roles and experience levels)
Benefits:
- Health, dental, and vision insurance
- 401(k) plan with company match
- Unlimited PTO
- Flexible work arrangements
Working Hours: Full-time (40 hours per week) with flexible scheduling
ASSUMPTION: The salary range is estimated based on industry standards for similar roles and experience levels. The actual salary may vary depending on the candidate's qualifications and the company's compensation structure.
📌 Applicant Insights
🔍 Company Context
Industry: Software Development, specifically focused on car ownership and insurance
Company Size: 201-500 employees (Mid-size company with a startup-like environment)
Founded: 2017 (8 years in operation)
Company Description:
- Jerry is America’s first and only AllCar™ app, redefining and improving all aspects of car ownership
- Offers a range of services, including insurance comparison and purchase, car diagnostics, driving insights, repair marketplace, and more
- Committed to constant innovation and improvement, using AI and machine learning to enhance the customer experience
Company Specialties:
- Insurance
- Artificial Intelligence
- Mobile Application Development
- Consumer Software
- Internet Technology
- Fintech
- Automotive
- Insurtech
Company Website: https://jerry.ai/
ASSUMPTION: Jerry is a fast-growing, innovative company with a strong focus on technology and customer experience. Working here offers opportunities for professional growth and exposure to cutting-edge technologies.
📊 Role Analysis
Career Level: Senior-level role with significant responsibility and autonomy
Reporting Structure: Reports directly to the VP of Insurance Operations and works cross-functionally with various teams
Work Arrangement: Remote OK, with flexible scheduling and unlimited PTO
Growth Opportunities:
- Potential to grow into a leadership role within the company as it continues to expand
- Opportunities to work on diverse projects and gain exposure to various aspects of the business
- Chance to learn from and collaborate with experienced leaders and team members
ASSUMPTION: This role offers significant growth potential as the company continues to scale and expand its offerings.
🌍 Location & Work Environment
Office Type: Remote OK, with physical offices in Palo Alto, CA; Toronto, ON; and Lockport, NY
Office Location(s): 430 Sherman Ave, Suite 305, Palo Alto, CA 94306, US; 615 Yonge St, Toronto, Ontario M4Y 1Z5, CA; 210 Walnut St, B2-312, Lockport, New York 14094, US
Geographic Context:
- The San Francisco Bay Area offers a vibrant tech industry, diverse culture, and a high cost of living
- Toronto is a major tech hub with a multicultural population and a lower cost of living compared to the Bay Area
- Lockport, NY, is a smaller city with a lower cost of living and a close-knit community
Work Schedule: Full-time (40 hours per week) with flexible scheduling and unlimited PTO
ASSUMPTION: The remote work arrangement offers flexibility and the ability to work from various locations, while the company's physical offices provide opportunities for in-person collaboration and networking.
💼 Interview & Application Insights
Typical Process:
- Phone or video screen with the hiring manager
- In-depth interviews with cross-functional team members
- Case study or project presentation
- Final interview with the VP of Insurance Operations
Key Assessment Areas:
- Problem-solving skills and strategic thinking
- Communication and collaboration skills
- Leadership and team management abilities
- Understanding of the insurance industry and marketplace dynamics
Application Tips:
- Highlight your management consulting experience and relevant achievements
- Tailor your resume and cover letter to emphasize your skills and experiences related to the required qualifications
- Prepare for behavioral and situational interview questions that focus on your problem-solving, leadership, and communication skills
ATS Keywords: Marketplace Automation, Growth Strategy, Team Management, Problem-Solving, Communication, Cross-Functional Collaboration, User Experience, Carrier Performance, Data Analysis, Leadership, Quantitative Analysis, Strategic Planning, Customer Retention, Conversion Optimization, AI Integration, Innovation
ASSUMPTION: The interview process is designed to assess your strategic thinking, problem-solving skills, and ability to work effectively with various teams. Being prepared with examples of your past achievements and a clear understanding of the role's requirements will help you succeed in the interview process.
🛠️ Tools & Technologies
- AI and machine learning technologies
- Data analysis and visualization tools
- Project management and collaboration software
- Communication and productivity tools (e.g., Slack, Google Workspace)
ASSUMPTION: Familiarity with AI and machine learning technologies, as well as data analysis and visualization tools, will be beneficial for this role.
👔 Cultural Fit Considerations
Company Values:
- Customer-centric
- Innovative and data-driven
- Collaborative and inclusive
- Accountable and results-oriented
Work Style:
- Fast-paced and dynamic
- Results-driven and focused on achieving business objectives
- Collaborative and cross-functional, with a strong emphasis on teamwork and communication
Self-Assessment Questions:
- Do you thrive in a fast-paced, dynamic environment, and are you comfortable with ambiguity and change?
- Are you able to work effectively with various teams and stakeholders, and do you have strong communication skills?
- Do you have a structured problem-solving framework and a data-driven approach to decision-making?
ASSUMPTION: Jerry values candidates who are innovative, data-driven, and able to work effectively in a collaborative, fast-paced environment. Strong communication skills and a structured problem-solving approach are essential for success in this role.
⚠️ Potential Challenges
- Managing multiple priorities and stakeholders in a fast-paced, dynamic environment
- Balancing strategic thinking and execution, with a focus on driving business outcomes
- Working effectively with various teams and stakeholders, including technical teams and C-suite executives
- Adapting to a rapidly changing business landscape and market dynamics
ASSUMPTION: This role presents unique challenges and opportunities for growth, requiring strong leadership, communication, and problem-solving skills to succeed.
📈 Similar Roles Comparison
- Unlike traditional management consulting roles, this position focuses on driving business outcomes and executing strategies within a specific industry (insurance)
- Compared to other fintech or insurtech roles, this position requires a strong background in management consulting and a proven track record in leadership roles
- Career progression in this role may involve moving into a leadership or executive position within the company as it continues to grow and expand
ASSUMPTION: This role offers a unique blend of management consulting and industry-specific experience, with significant growth potential as the company continues to scale.
📝 Sample Projects
- Developing and implementing a strategic plan to optimize Jerry’s quoting engine and automation infrastructure
- Conducting a comprehensive analysis of the insurance marketplace to identify opportunities for growth and optimization
- Leading a cross-functional team to improve the user experience and drive critical outcomes for the insurance marketplace
ASSUMPTION: These sample projects illustrate the strategic, analytical, and collaborative nature of the role, requiring strong leadership, communication, and problem-solving skills to succeed.
❓ Key Questions to Ask During Interview
- Can you describe the current state of Jerry’s quoting engine and automation infrastructure, and what are the key priorities for this role?
- How does this role collaborate with other teams, such as product, engineering, and analytics, to achieve business objectives?
- What are the most significant challenges facing the insurance marketplace, and how can this role address them to drive business growth?
- How does Jerry support the professional development and growth of its employees, and what opportunities exist for growth in this role?
- What is the company’s long-term vision for the insurance marketplace, and how does this role contribute to achieving that vision?
ASSUMPTION: Asking these questions demonstrates your interest in the role and its strategic importance to the company, while also providing valuable insights into the company’s culture and priorities.
📌 Next Steps for Applicants
To apply for this position:
- Submit your application through this link
- Tailor your resume and cover letter to highlight your management consulting experience and relevant achievements
- Prepare for behavioral and situational interview questions that focus on your problem-solving, leadership, and communication skills
- Research Jerry’s business model, market position, and competitive landscape to demonstrate your understanding of the company and its industry
- 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.
