Loyalty Program Strategist - Freelance - Remote

Right Side Up; United States; Remote; USD 110,000 - 207,000; Full time

Job summary

Right Side Up is seeking freelance Loyalty Program Strategists to help clients design, evaluate, and scale loyalty programs that drive growth. This is a senior, project-based role for professionals with a track record across B2B, B2C, and marketplaces.

Contract projects typically range from 10–20 hours per week with diverse client needs. You will collaborate with product, marketing, and finance teams to translate strategy into executable proposals, measure outcomes, and guide program structure

Qualifications

• 8+ years designing and building loyalty programs across B2B/B2C/marketplaces.
• Track record evaluating unit economics behind loyalty investments, not just design.
• Strong blend of product and marketing instincts with a clear read on what motivates action.
• Comfortable cross-functional work with product, engineering, and finance stakeholders.
• Experience translating strategy into executable frameworks for product/engineering teams.
• Hands-on operator who has shipped loyalty programs, not just advised on them.
• Able to structure ambiguity into clear deliverables in open-ended engagements.

Responsibilities

• Audit existing loyalty programs, including mechanics and unit economics.
• Evaluate if loyalty is the right growth lever for a business segment.
• Design loyalty strategy and mechanics for B2B, B2C, and marketplace models.
• Build business cases connecting loyalty investment to retention and revenue growth.
• Assess customer behavior, segmentation, and what motivates action.
• Benchmark against competitors and translate insights to actionable proposals.
• Partner with product, marketing, and finance to align scope and tradeoffs.
• Translate strategy into execution-ready frameworks for engineering teams.
• Define success metrics and measurement frameworks for loyalty programs.
• Advise on program structure, including tiering, earn/burn, and personalization.
• Present findings to senior stakeholders and executives.

Skills

Loyalty design

Unit economics

Cross-functional collaboration

Product & marketing instincts

Executive communication

Tools

Yotpo

Smile.io

Annex Cloud

Bond

Job description

About Right Side Up

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.