[Hiring] Lead Customer Strategist REMOTE USA
Position: Lead Customer Strategist
Date Posted: April 22, 2026
Industry: Insurance / Commercial Lines / Insurtech
Employment Type: Full Time
Experience: Minimum 10 years relevant experience
OR Bachelor’s Degree with minimum 7 years of relevant experience in digital product, customer experience, or multi-channel delivery roles
Qualification: Bachelor’s Degree in Business, Technology, Marketing, Insurance, or related field (or equivalent professional experience)
Salary: $98,400 – $131,200 per year + up to 30% annual Gainshare incentive based on performance
Location: United States (REMOTE)
Company: Progressive Insurance
Description:
Progressive is committed to building a workplace where professionals can continuously grow, develop, and advance in their careers. This opportunity offers a chance to contribute to a forward-moving organization focused on innovation, customer experience, and commercial insurance excellence.
As a Lead Customer Strategist within the Commercial Lines Acquisition division, you will play a key role in expanding top-of-funnel business growth. Your focus will be on strengthening Progressive’s presence across external insurance quoting platforms by collaborating with insurance agents, external vendors, and internal technology teams.
In this role, you will take ownership of enhancing digital integrations and improving how customers and agents interact with third-party quoting systems. You will analyze user journeys, identify friction points in the customer funnel, and work closely with technical teams to design and implement effective solutions that improve conversion and overall experience.
You will also manage and guide vendor relationships throughout their lifecycle, ensuring alignment between sourcing, legal, security, and business requirements. This includes supporting contract execution, evaluating performance, and driving continuous improvements in integration outcomes.
This position is a key contributor to the vision of making Progressive the leading destination for business owners and insurance agents in the commercial insurance space.
Key Responsibilities:
• Lead strategy and execution for commercial lines acquisition through digital and external quoting platforms
• Partner with internal technical teams to enhance system integrations and improve user experience
• Identify gaps and friction points in customer and agent journeys using data-driven analysis
• Translate complex business challenges into structured, solvable problems
• Collaborate with insurance agents, vendors, and stakeholders to strengthen platform performance
• Manage vendor relationships including requirements, contracts, delivery oversight, and accountability
• Work cross-functionally with sourcing, legal, and security teams for contract and integration alignment
• Support continuous optimization of funnel performance and conversion outcomes
Required Qualifications:
• 10+ years of relevant professional experience in digital product, customer strategy, or multi-channel delivery
OR
• Bachelor’s degree with 7+ years of relevant experience in similar domains
Preferred Skills & Experience:
• Strong understanding of how user experience, analytics, and technology impact business growth
• Ability to work with both structured and ambiguous problems using qualitative and quantitative insights
• Experience working in collaborative, cross-functional team environments
• Background in vendor management, integration processes, and contract execution
• Comfortable working in highly technical ecosystems and digital platforms
• Experience in Property & Casualty (P&C) insurance, especially Commercial Lines is highly preferred
Compensation & Benefits:
• Competitive annual salary with performance-based incentives
• 401(k) with company match up to 6%
• Comprehensive medical, dental, and vision coverage with preventive care benefits
• Health savings accounts, flexible spending accounts, and life insurance options
• Paid time off including volunteer leave and family leave programs
• Short-term and long-term disability coverage
• Inclusive workplace culture with employee resource groups
• Career development programs and tuition assistance
• Wellness programs including mental health support and onsite fitness facilities at select locations
Progressive has been recognized as a 2025 Top Workplace for Innovation, Values, Leadership, Work-Life Flexibility, and Compensation & Benefits.
Applicants must be legally authorized to work in the United States without current or future sponsorship requirements. Progressive does not provide employment sponsorship for this role, including H-1B, F-1 CPT/OPT/STEM OPT, O-1, E-3, or TN visa statuses.
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