Sr. Director, Customer Strategy & Insights

Total Wine & More; North Bethesda (MD); On-site; USD 200,000 - 260,000; Full time

Benefits offered by this job

PTO

Store discounts

Health care plans

401(k)

Disability insurance

Parental leave

Pet insurance

College tuition assistance

Career development

Consumer classes

Job summary

Total Wine & More, a leader in beverage retail, seeks a Sr. Director of Customer Strategy & Insights to define our enterprise customer vision and drive growth through insights, segmentation, and personalized experiences.

You will steer cross-functional initiatives spanning acquisition, engagement, loyalty, and CLV, reporting to the Chief Customer & Strategy Officer. You will shape customer strategy and governance, translating market data into actionable plans that differentiate Total Wine & More

Qualifications

• Bachelor’s degree required; MBA preferred; 10+ years of leadership in customer strategy and insights.
• Deep expertise in segmentation, personalization, CLV, retention, and journey management across channels.
• Track record translating customer insights into enterprise strategy and measurable outcomes.
• Exceptional leadership and communication skills in large, matrixed organizations.

Responsibilities

• Define and lead Total Wine & More’s enterprise customer strategy and vision.
• Act as customer thought leader to anticipate needs and fuel growth opportunities.
• Integrate research, analytics, and market intel into actionable insights for marketing, merchandising, digital, and stores.
• Develop and advance the customer flywheel: segmentation, loyalty, personalization, CLV.
• Drive the customer experience strategy across journeys and touchpoints.
• Lead customer-centric innovation with pilots and test-and-learn initiatives.
• Partner across the enterprise to embed insights into planning and investments.
• Build and lead a high-performing Customer Strategy & Insights organization.

Skills

Leadership

Strategic thinking

Cross-functional leadership

Customer insights

Analytics

Communication

Market dynamics

Executive collaboration

Education

MBA

Bachelor’s in Business/Marketing

Tools

Tableau

SQL

Excel

Job description

About the Role

Total Wine & More is seeking a Sr. Director, Customer Strategy & Insights to join our growing Corporate Strategy team. This role will define the enterprise customer vision and strategic priorities that guide how the company acquires, understands, serves, engages, and grows its customer relationships. This role will help Total Wine & More understand the customer better than anyone else, translating customer insights into enterprise strategy, differentiated experiences, growth initiatives, and measurable business results. As a key strategic advisor to executive leadership, this role shapes enterprise priorities through a deep understanding of customer needs, behaviors, market dynamics, competitive trends, and emerging opportunities.

As the steward of Total Wine & More's customer agenda, this leader establishes enterprise priorities, defines the most important customer and business questions to solve, and steers cross-functional initiatives spanning customer acquisition, segmentation, personalization, engagement, loyalty, retention, and customer lifetime value (CLV). This role reports to the Chief Customer & Strategy Officer.

You will

• Define and lead Total Wine & More’s enterprise customer strategy, establishing the long-term vision, strategic priorities, and customer outcomes that drive sustainable growth, loyalty, and competitive differentiation.
• Serve as the organization’s customer thought leader, leveraging customer, market, competitive, and industry insights to anticipate evolving customer needs, identify growth opportunities, and influence enterprise decision-making.
• Build a holistic understanding of the customer by integrating research, behavioral data, analytics, market intelligence, and customer feedback into actionable insights that inform strategies across marketing, merchandising, digital, store operations, and customer experience.
• Lead the development of the customer flywheel, including segmentation, loyalty, personalization, retention, and customer lifetime value (CLV) strategies, ensuring investments are focused on the highest-impact opportunities.
• Define and advance the enterprise customer experience strategy, leading customer journey management and experience design efforts that create connected, differentiated, and customer-centric experiences across all touchpoints.
• Champion customer-centric innovation by leading opportunity identification, concept development, experimentation, pilot programs, and test-and-learn initiatives that accelerate growth and organizational learning.
• Partner across the enterprise to activate customer strategies, embedding customer insights, segmentation, and personalization into customer-facing experiences while influencing strategic planning, investment decisions, and major growth initiatives.
• Build and lead a high-performing Customer Strategy & Insights organization, establishing governance, measurement frameworks, and talent strategies that drive accountability, innovation, customer obsession, and business results.

You will come with

• Bachelor's degree in Business, Marketing, Analytics, Economics, or a related field; MBA or other advanced degree preferred.
• 10+ years of progressive leadership experience across customer strategy, consumer insights, analytics, customer experience, innovation, marketing strategy, consulting, or related disciplines, with a proven track record of driving transformational customer and business outcomes.
• Deep expertise in customer strategy and growth, including segmentation, personalization, acquisition, engagement, loyalty, retention, customer lifetime value (CLV), customer experience, and customer journey management across physical and digital channels.
• Proven ability to translate customer insights into enterprise strategy, leveraging research, analytics, market intelligence, experimentation, and innovation to drive differentiated experiences and measurable business results.
• Exceptional enterprise leadership, influence, and communication skills, with demonstrated success leading complex cross-functional initiatives, shaping executive decision-making, and operating effectively in large, matrixed organizations.
• Strong commercial acumen and strategic foresight, coupled with experience building high-performing teams and cultivating a culture of customer obsession, innovation, collaboration, and accountability.

We offer

• Paid Time Off (PTO)
• Generous store discounts
• Health care plans (medical, prescription, dental, vision)
• 401(k), HSA, FSA, Pre-tax commuter benefits
• Disability & life insurance coverage
• Paid parental leave
• Pet insuranceCritical illness and accident insurance
• Discounted home and auto insurance
• College tuition assistance
• Career development & product training
• Consumer classes
• & More!

Crafted for you

We recognize our team members are our biggest asset, and we value the critical role each play in contributing to the company’s success. It is our commitment to support and provide access to the resources needed to take care of their health and wellbeing. That is why we offer a variety of benefits, tools, and resources to support through our Total Rewards program.

Total Wine & More considers several factors when establishing compensation. Compensation may vary based on a number of factors including, but not limited to, market location, job-related knowledge, skills and/or experience. The actual hourly rate will equal or exceed the required minimum wage applicable to the job location. Estimated salaries determined by third parties have not been validated by Total Wine & More.

Total Wine & More is an equal opportunity employer and all qualified applicants will receive consideration for employment without discrimination based on race, color, religion, national origin, sex, sexual orientation, age, marital status, veteran status, disability, or any other characteristic protected by applicable law. Total Wine & More makes reasonable accommodations during all aspects of the employment process, including during the interview process. Total Wine & More is a Drug Free Workplace.

The information provided above indicates the general nature and level of work required of the position and is not a comprehensive list of all responsibilities or qualifications. Benefits list is only a highlight of some of the benefits offered to team members; eligibility for certain benefits apply. The anticipated close date of this posting is 120 days from the posted date indicated above.