About this Loyalty Program Strategist - Freelance - Remote role at Rightsideup
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.
About the Role
Responsibilities
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Audit existing loyalty or rewards programs, including mechanics, redemption structures, and unit economics.
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Evaluate whether a loyalty program is the right growth lever for a given business, product, or customer segment, and make the case either way.
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Design loyalty program strategy and mechanics tailored to B2B, B2C, and marketplace business models.
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Build the business case connecting loyalty investment to retention, repeat behavior, and revenue growth.
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Assess customer behavior, segmentation, and what motivates a given audience to take action.
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Benchmark against competitors and comparable loyalty programs, and know when a comparison does or doesn’t translate.
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Partner closely with product, marketing, and finance stakeholders to align on scope, priorities, and tradeoffs.
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Translate strategy into a clear, execution-ready framework or proposal that product and engineering teams can build against.
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Define success metrics and measurement frameworks for new or evolved loyalty programs.
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Advise on program structure, including tiering, earn/burn mechanics, and personalization.
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Present findings and recommendations to senior stakeholders, including executive teams.
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Stay current on loyalty and retention best practices across industries and business models.
Requirements
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8+ years designing and building loyalty programs, ideally across B2B, B2C, and/or marketplace businesses.
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Track record evaluating the unit economics and business case behind loyalty investments, not just program design.
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Strong blend of product and marketing instincts, with a clear read on what motivates people to take action.
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Comfortable operating cross-functionally with product, engineering, and finance stakeholders.
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Experience translating strategy into frameworks that product and engineering teams can execute against.
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Hands-on operator who has shipped loyalty programs, not just advised on them.
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Comfortable in open-ended, evaluative engagements, structuring ambiguity into a clear deliverable.
Tools & Platforms
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Familiarity with loyalty and rewards platforms such as Yotpo, Smile.io, Annex Cloud, Bond, or custom-built systems.
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CRM and lifecycle marketing tools.
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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!