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About the Role

We are seeking freelance Loyalty Program Strategists to help our clients design, evaluate, and scale loyalty programs that drive business growth. This is a senior specialty role for individuals who have built and launched loyalty programs at leading brands across B2B, B2C, and marketplace models, combining product and marketing expertise. Contract projects typically range from 10–20 hours per week.

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, including executive teams.
• 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, with a clear read on what motivates people to take action.
• 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, structuring ambiguity into a clear deliverable.

Skills

• Loyalty program strategy
• Program design
• Unit economics analysis
• Customer behavior assessment
• Segmentation
• Competitive benchmarking
• Stakeholder management
• Framework development
• Metrics definition
• Retention strategies
• Product marketing
• Yotpo
• Smile.io
• Annex Cloud
• Bond
• CRM tools
• Lifecycle marketing tools
• Analytics platforms

Work Type

• Freelance
• Contract

Experience Level

• Senior

About the Company

• Right Side Up is a collective of premium marketing talent.
• We are trusted by early-stage ventures, fast-growing tech companies, and Fortune 500 teams for Growth.
• Our clients include Stitch Fix, Sephora, Yelp, Sun Basket, Crunchbase, DoorDash, and Calm.