Loyalty Program Strategist - Freelance - Remote

About Right Side Up

Please note, this posting is to highlight joining Right Side Up's talent collective specifically and is not representing an internal full-time role, or a current opportunity with a client.

Right Side Up is a collective of premium marketing talent—with all of the marketing chops, and none of the agency fluff. We're trusted by the most respected early-stage ventures, the fastest-growing tech companies, and well-established Fortune 500 teams to do one thing better: Growth. We have over 250+ clients including Stitch Fix, Sephora, Yelp, Sun Basket, Crunchbase, DoorDash, Calm, and more.

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About the Role

We're seeking freelance Loyalty Program Strategists to help our clients design, evaluate, and scale loyalty programs that drive real business growth. This is a niche, senior specialty: we're looking for people who have actually built and shipped loyalty programs at leading brands, across B2B, B2C, and marketplace models, and who bring a blend of product and marketing instincts to the work. Contract projects typically range from 10–20 hours per week, depending on client needs and project scope.

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, and make the case either way.
• 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, and know when a comparison does or doesn’t translate.
• 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 that product and engineering teams can build against.
• 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, not just program design.
• 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, not just advised on them.
• Comfortable in open-ended, evaluative engagements, structuring ambiguity into a clear deliverable.

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.

Why Right Side Up

Join a team that values expertise, flexibility, and meaningful work with some of the most innovative brands in the world. Exciting opportunities are available now — apply today to join our network of experts!

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