Sr. Director, Customer Strategy & Insights

Total Wine & More•SSC - MD, MD
•$218,680 - $306,130

About The Position

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.

Requirements

  • 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.

Responsibilities

  • 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.

Benefits

  • 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 insurance
  • Critical illness and accident insurance
  • Discounted home and auto insurance
  • College tuition assistance
  • Career development & product training
  • Consumer classes
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