Loyalty Program Strategist - Freelance - Remote

Right Side Up is seeking freelance Loyalty Program Strategists to help clients design, evaluate, and scale loyalty programs that drive real business growth.

This is a niche, senior specialty role requiring experience building and shipping loyalty programs at leading brands across B2B, B2C, and marketplace models.

Responsibilities

• Audit existing loyalty or rewards programs, including mechanics, redemption structures, and unit economics.
• Evaluate whether a loyalty program is the right growth lever for a given business, product, or customer segment.
• Design loyalty program strategy and mechanics tailored to B2B, B2C, and marketplace business models.
• Build the business case connecting loyalty investment to retention, repeat behavior, and revenue growth.
• Assess customer behavior, segmentation, and what motivates a given audience to take action.
• Benchmark against competitors and comparable loyalty programs.
• Partner closely with product, marketing, and finance stakeholders to align on scope, priorities, and tradeoffs.
• Translate strategy into a clear, execution-ready framework or proposal.
• Define success metrics and measurement frameworks for new or evolved loyalty programs.
• Advise on program structure, including tiering, earn/burn mechanics, and personalization.
• Present findings and recommendations to senior stakeholders.
• Stay current on loyalty and retention best practices across industries and business models.

Requirements

• 8+ years designing and building loyalty programs, ideally across B2B, B2C, and/or marketplace businesses.
• Track record evaluating the unit economics and business case behind loyalty investments.
• Strong blend of product and marketing instincts.
• Comfortable operating cross-functionally with product, engineering, and finance stakeholders.
• Experience translating strategy into frameworks that product and engineering teams can execute against.
• Hands-on operator who has shipped loyalty programs.
• Comfortable in open-ended, evaluative engagements.

Tools & Platforms

• Familiarity with loyalty and rewards platforms such as Yotpo, Smile.io, Annex Cloud, Bond, or custom-built systems.
• CRM and lifecycle marketing tools.
• Analytics platforms for cohort, retention, and unit economics analysis.