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.

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!

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.