Strategic Product Leader - Remote

CSAA Insurance Group, a AAA Insurer • Washington, DC

6d • $152,010 - $202,550 • Remote

About The Position

CSAA Insurance Group (CSAA IG), a AAA insurer, is one of the leading personal lines property and casualty insurance groups in the United States. Here, every employee shapes our mission. We build innovative, human-centered solutions that help AAA members prevent, prepare for, and recover from life's uncertainties. You will join a collaborative, inclusive culture where your strengths have room to grow and your ideas can drive real impact. Step into a role where you can contribute to our shared success through meaningful work. We are actively hiring for Strategic Product Leader - Remote! Your Role: As a Strategic Product Leader (Chief of Staff), you’ll partner with the EVP of Personal Lines Product Management to turn strategy into action—driving alignment, supporting key decisions, and keeping priorities moving across business, technology, finance, and operations. You’ll also shape executive communications and operating rhythms to keep the leadership team focused and effective. Your Work: Serve as a trusted partner and extension of the EVP of Personal Lines Product Management, operating at the center of strategy, execution, and organizational effectiveness. This is a high-impact, highly visible role designed for a senior operator who thrives in complexity and can translate strategic priorities into coordinated action across the enterprise. You will work across business, technology, finance, and operations to drive alignment, accelerate execution, and elevate decision-making for one of the company’s most critical divisions. You will also play a key role in shaping executive communications and ensuring the EVP’s priorities are clearly and effectively represented across internal and external audiences. The EVP and leadership team are focused on the right priorities at the right time, supported by a clear and effective operating cadence Strategic direction is translated into action quickly and consistently, with minimal need for escalation or intervention Key deliverables — especially executive presentations — are developed to a near-final state, requiring only refinement and input The EVP’s time is protected and optimized, with questions, decisions, and requests handled at the appropriate level Stakeholders experience clarity, responsiveness, and consistency, with the ability to rely on you as a trusted extension of the EVP

Requirements

• 10+ years in consulting, strategy, operations, or similar roles with significant executive exposure
• Experience working directly with senior leaders on high-priority initiatives
• Bachelor's degree in related area (business or a related field) or an equivalent combination of education and experience.
• Proven ability to operate at both strategic and execution levels in complex environments
• Exceptional judgment and decision-making, including in ambiguous situations
• Strong influence skills, with the ability to lead without formal authority across senior stake-holders
• Demonstrated success in driving complex, cross-functional initiatives to completion
• Excellent communication and storytelling skills, particularly for executive audiences
• Ability to synthesize complex information and focus teams on what matters most
• High degree of ownership, accountability, and follow-through

Nice To Haves

• Prior Chief of Staff or equivalent experience strongly preferred
• Experience in Property & Casualty insurance preferred
• Experience applying data, analytics, or AI-enabled approaches to business problems
• Experience with financial planning, headcount management, or operational metrics
• Track record of improving organizational effectiveness and operating cadence
• Actively shapes our company culture (e.g., supporting employee resource groups, mentoring employees, volunteering, joining cross-functional projects)
• Champions our cultural norms (e.g., willing to have cameras when it matters: helping onboard new team members, building relationships, etc.)
• Demonstrates a company ownership mindset, thinking beyond boundaries of their own area
• Travels as needed for role, including divisional / team meetings and other in-person meetings
• Fulfills business needs, which may include investing extra time, helping other teams, etc.

Responsibilities

• Serve as a trusted partner and extension of the EVP of Personal Lines Product Management, operating at the center of strategy, execution, and organizational effectiveness.
• Translate strategic priorities into coordinated action across the enterprise.
• Drive alignment, accelerate execution, and elevate decision-making.
• Shape executive communications and ensuring the EVP’s priorities are clearly and effectively represented across internal and external audiences.
• Ensure the EVP and leadership team are focused on the right priorities at the right time, supported by a clear and effective operating cadence
• Translate Strategic direction into action quickly and consistently, with minimal need for escalation or intervention
• Develop Key deliverables — especially executive presentations — to a near-final state, requiring only refinement and input
• Protect and optimize The EVP’s time, with questions, decisions, and requests handled at the appropriate level
• Ensure Stakeholders experience clarity, responsiveness, and consistency, with the ability to rely on you as a trusted extension of the EVP

Benefits

• Recognition: We offer a total compensation package, annual bonus eligibility for most roles, 401(k) with a company match, and so much more!
• Career Growth: We believe in growth for everyone. Here at CSAA IG, leaders and mentors partner with employees to align interests, unlock development opportunities, and support long‑term success.
• Flexible Workplace: We embrace a remote-first culture through our Flexible Workplace. Most employees hold Home-Flex roles, working primarily from home, often with the flexibility to work from various locations including CSAA offices. Our flexible workplace empowers you to balance remote work with intentional in‑person moments that deepen connection and collaboration.
• Inclusion and Belonging: An inclusive and welcoming workplace is the cornerstone of our success. By fostering an environment where people feel valued and heard, we deepen our ability to understand and meet the unique needs of our members. This strengthens innovation and enhances our products and services, giving us a competitive edge in the market.
• Sustainability: As climate change leads to more frequent and severe weather events, we are taking bold action to build more resilient communities and reduce our environmental impact.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level