📌 Core Information
🔹 Job Title: Director, Business Operations (Marketplace Growth)
🔹 Company: Jerry.ai
🔹 Location: Remote (United States)
🔹 Job Type: Full-Time
🔹 Category: Business Operations, Management Consulting
🔹 Date Posted: July 30, 2025
🔹 Experience Level: 5-10 years
🔹 Remote Status: Remote OK
🚀 Job Overview
Key aspects of this role include:
- Scaling Jerry's core insurance business to reach 50M customers and become a $10B business
- Owning the systems, strategy, and execution behind Jerry’s quoting engine, automation infrastructure, and carrier performance
- Working cross-functionally with product, engineering, and analytics to create a seamless user experience and ensure ongoing carrier success
- Driving critical outcomes for the insurance marketplace, such as loss ratio, retention, and conversion
ASSUMPTION: This role requires a high level of strategic thinking, cross-functional collaboration, and a strong background in management consulting to succeed.
📋 Key Responsibilities
✅ Own the systems, strategy, and execution behind Jerry’s quoting engine, automation infrastructure, and carrier performance
✅ Work cross-functionally with product, engineering, and analytics to create a seamless user experience and ensure ongoing carrier success
✅ Drive critical outcomes for the insurance marketplace, such as loss ratio, retention, and conversion
✅ Collaborate with leadership to define and achieve ambitious growth targets
✅ Hire, manage, and develop high-performing teams to support business operations
ASSUMPTION: This role involves a high degree of ownership, strategic decision-making, and team management, requiring strong leadership and problem-solving 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, Boston Consulting Group preferred)
Required Skills:
- Proven track record of hiring and managing high-performing teams
- Structured framework for problem-solving and first principles thinking
- Excellent communication skills with various stakeholders, including technical teams and C-suite
- Strong strategic thinking and cross-functional collaboration skills
- Familiarity with insurance marketplace, user experience, automation, and performance metrics
Preferred Skills:
- Experience with AI and machine learning
- Background in insurance or fintech industry
ASSUMPTION: Given the role's focus on growth and strategic decision-making, candidates with a strong management consulting background and relevant industry experience are most likely to succeed.
💰 Compensation & Benefits
Salary Range: $150,000 - $200,000 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 hours
- Equity compensation
Working Hours: Full-time, flexible work hours with a focus on results and outcomes
ASSUMPTION: The salary range is estimated based on market data for similar roles in the United States. Actual compensation may vary based on experience and performance.
📌 Applicant Insights
🔍 Company Context
Industry: Fintech, Insurance Technology (Insurtech)
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
- Offers a range of services, including insurance, buy/sell, registration, loans, safety, repairs, and parking
- Backed by artificial intelligence and machine learning, focusing on user experience and personalization
Company Specialties:
- Insurance
- Artificial intelligence
- Mobile application
- Consumer software
- Internet technology
- Fintech
- Automotive
- Insurtech
Company Website: https://www.jerry.ai
ASSUMPTION: Jerry.ai is a well-funded, rapidly growing fintech company with a strong focus on innovation and user experience in the car ownership market.
📊 Role Analysis
Career Level: Mid to Senior-level management role
Reporting Structure: Reports directly to the VP of Insurance Operations
Work Arrangement: Remote OK, with flexible work hours and a focus on results and outcomes
Growth Opportunities:
- Potential to grow into a leadership role within the company as it continues to expand
- Opportunity to work closely with senior leadership and influence strategic decisions
- Chance to gain experience in a fast-growing fintech company and learn from industry experts
ASSUMPTION: This role offers significant growth potential for the right candidate, as Jerry.ai continues to scale and expand its offerings.
🌍 Location & Work Environment
Office Type: Remote (no physical office)
Office Location(s): Palo Alto, CA; Toronto, ON; Lockport, NY
Geographic Context:
- Remote work allows for flexibility in location, with a focus on results and outcomes
- Company headquarters are in Palo Alto, CA, with additional offices in Toronto, ON, and Lockport, NY
- Jerry.ai has a diverse, global team with remote team members in four countries
Work Schedule: Full-time, flexible work hours with a focus on results and outcomes
ASSUMPTION: The remote work environment at Jerry.ai offers a high degree of flexibility and autonomy, with a strong focus on results and outcomes.
💼 Interview & Application Insights
Typical Process:
- Phone or video screen with the hiring manager
- Case study or project presentation to the team
- Final round interviews with senior leadership
Key Assessment Areas:
- Problem-solving and strategic thinking skills
- Cross-functional collaboration and communication skills
- Leadership and team management abilities
- Industry knowledge and relevant experience
Application Tips:
- Highlight your management consulting experience and relevant industry knowledge
- Tailor your resume and cover letter to emphasize your problem-solving, strategic thinking, and leadership skills
- Prepare a case study or project presentation that demonstrates your ability to drive results and make data-driven decisions
ATS Keywords: Management Consulting, Team Management, Problem-Solving, Communication, Strategic Thinking, Cross-Functional Collaboration, User Experience, Automation, Performance Metrics, Insurance Marketplace, Data Analysis, Leadership, Customer Retention, Revenue Growth, Market Strategy, AI and Machine Learning
ASSUMPTION: The interview process at Jerry.ai is designed to assess candidates' strategic thinking, problem-solving, and leadership skills, as well as their ability to work effectively in a cross-functional team.
🛠️ Tools & Technologies
- AI and machine learning platforms
- Data analysis and visualization tools
- Project management software
ASSUMPTION: The specific tools and technologies used in this role will depend on the candidate's area of focus and the projects they work on.
👔 Cultural Fit Considerations
Company Values:
- Customer-centric
- Innovative
- Data-driven
- Collaborative
- Results-oriented
Work Style:
- Fast-paced and dynamic
- Focused on results and outcomes
- Collaborative and cross-functional
- Data-driven and analytical
Self-Assessment Questions:
- Do you thrive in a fast-paced, dynamic environment?
- Are you comfortable working cross-functionally and collaborating with various teams?
- Do you have a strong track record of driving results and making data-driven decisions?
ASSUMPTION: Jerry.ai values candidates who are customer-centric, innovative, data-driven, collaborative, and results-oriented, with a strong work ethic and a passion for improving car ownership.
⚠️ Potential Challenges
- Working in a fast-paced, dynamic environment may require strong adaptability and time management skills
- Collaborating with various teams and stakeholders may require strong communication and interpersonal skills
- Driving results and making data-driven decisions may require a high level of analytical and problem-solving skills
- Working remotely may require strong self-motivation and time management skills
ASSUMPTION: While this role offers significant growth potential and a dynamic work environment, it also presents unique challenges that require strong skills and adaptability.
📈 Similar Roles Comparison
- This role is unique in its focus on scaling a fintech company's core insurance business and driving critical outcomes for the insurance marketplace
- Similar roles in management consulting or insurance industry may not require the same level of strategic thinking, cross-functional collaboration, or team management
- Career progression in this role may involve moving into a leadership position within the company as it continues to grow and expand
ASSUMPTION: This role is unique in its focus on driving growth and strategic decision-making within a fast-growing fintech company, offering significant growth potential and a dynamic work environment.
📝 Sample Projects
- Developing and implementing a new quoting engine and automation infrastructure to improve user experience and carrier performance
- Analyzing and optimizing carrier performance metrics to drive critical outcomes for the insurance marketplace
- Collaborating with product, engineering, and analytics teams to create a seamless user experience and ensure ongoing carrier success
ASSUMPTION: The specific projects in this role will depend on the candidate's area of focus and the company's strategic priorities at the time of hire.
❓ Key Questions to Ask During Interview
- Can you describe the company's strategic priorities for the next 12-24 months and how this role fits into that plan?
- How does the company support the professional development and growth of its employees?
- Can you provide examples of how the company has successfully scaled its core insurance business in the past, and what lessons were learned from those experiences?
- How does the company approach cross-functional collaboration and communication, and what tools or processes are in place to facilitate that?
- What are the key performance indicators (KPIs) for this role, and how will success be measured?
ASSUMPTION: Asking thoughtful, strategic questions during the interview process demonstrates your interest in the role and your ability to think critically about the company's priorities and growth potential.
📌 Next Steps for Applicants
To apply for this position:
- Submit your application through the Ashby job posting
- Tailor your resume and cover letter to highlight your management consulting experience, problem-solving skills, and strategic thinking abilities
- Prepare a case study or project presentation that demonstrates your ability to drive results and make data-driven decisions
- Follow up with the hiring manager one week after submitting your application to express your continued interest in the role
⚠️ This job description contains AI-assisted information. Details should be verified directly with the employer before making decisions.
