Head of Loyalty

TrueLoyalSan Antonio, TX
Remote

About The Position

TrueLoyal is seeking a Head of Loyalty to serve as the company's expert in loyalty programs. This role involves both internal work (70%) and external market engagement (30%). The position exists to address the market's need for practical, experienced guidance on loyalty program design and economics, differentiating TrueLoyal from competitors who offer similar software features but lack hands-on expertise. The Head of Loyalty will leverage existing resources like customer call recordings, data from over 300 consumer brands, a strategy practice, and AI capabilities, working alongside data and AI teams. The company targets mid-market consumer brands ($50M-$500M in revenue) selling through major retailers and their own e-commerce sites, primarily in North America with some CPG reach into Europe. Buyers are typically at the VP or Director level, including brand, e-commerce, retention managers, and CMOs. A key challenge for these customers is fragmented identity and second-hand purchase data due to not owning their point-of-sale systems.

Requirements

  • Deep, practical knowledge of loyalty programs, including experience building, running, launching, relaunching, or owning a significant part of a loyalty program.
  • Understanding of program mechanics such as earn rates, tiers, redemption behavior, breakage, and economics.
  • Knowledge of the financial aspects of loyalty programs, including liability, accrual, and impact on CFOs.
  • Experience with programs that have gone 'flat' and understanding of the causes.
  • Brand or category experience in consumer goods or retail.
  • Familiarity with programs where the brand does not control the point of sale (e.g., third-party retail, DTC with receipt-based or inferred purchase data).
  • Strong writing and production skills, with a preference for producing work directly.
  • Experience using AI tools to enhance productivity.
  • Comfort and effectiveness presenting on stage and in smaller group settings.

Nice To Haves

  • Experience directing work rather than producing it.
  • A track record of producing research that leads to action.

Responsibilities

  • Own program economics as the standard for measurement, including earn/burn structures, tier design, breakage assumptions, redemption behavior, and pricing.
  • Build loyalty program designs and conduct account reviews with actionable recommendations.
  • Model financial liability and accrual for program designs to ensure they are CFO-ready.
  • Produce loyalty work at scale, utilizing AI and other tools, setting a high standard for all loyalty-related output.
  • Develop deep knowledge of the loyalty market by analyzing call data and program performance across 300+ brands.
  • Identify market trends, working categories, and best practices to inform product development.
  • Translate market insights into a demand case for new product features, collaborating with the VP of Product on the roadmap.
  • Shape the company's go-to-market strategy and influence product bets.
  • Train the company's AI to autonomously produce loyalty program designs, account reviews, and content.
  • Collaborate with data and AI teams to productize AI-driven loyalty program design.
  • Represent TrueLoyal externally at loyalty conferences, panels, podcasts, and analyst conversations.
  • Participate in pre-sales calls to provide expert insights and post-sales support for clients facing program challenges.
  • Write content that sparks discussion and influences the market.

Benefits

  • Health insurance plan with $0 deductible and $0 co-pay.
  • Dental and vision insurance plans.
  • Flexible spending account option.
  • Open PTO Policy.
  • 9 paid holidays per year.
  • Participation in our 401(k) savings plan.
  • Company-paid Life and AD&D coverage.
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