Principal, Lifecycle Automations & Incentives

Meet Upside:

We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retail—profit measurement, attribution, and incrementality—to provide users with more value on their everyday purchases and brick-and-mortar businesses with new, profitable customers. We’ve helped millions of users earn 2 to 3 times more cashback than any other product, and hundreds of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year, and that value goes directly back to our retailer partners, the consumers they serve, and important sustainability initiatives.

The Impact You'll Make:

As the Principal, Lifecycle Automations & Incentives, you will be the primary architect behind accelerating the scale of an automated, hyper-personalized, and scalable lifecycle growth engine. We are looking for a seasoned lifecycle leader and growth strategist capable of operating at the absolute intersection of consumer psychology, data-driven automation, and active financial engineering.

You’ll report to the Director of Lifecycle Marketing, and together you will drive strategy, execution, experimentation and regular optimization on two of the most critical levers for Upside’s growth: a full-funnel "core" lifecycle ecosystem tightly aligned with consumer growth goals and the strategic, profitable deployment of a large incentive bonus budget to help influence consumer behavior.

What You'll Do:

Scale the Core & Drive Multi-Vertical (MV) Ecosystem Growth

• Architect the Automated Funnel: Lead "Core Lifecycle" workstreams, helping us evolve from ad-hoc, one-off sends to a robust, automated ecosystem. You will personally design, build, instrument, and optimize sophisticated lifecycle automations across onboarding, habituation (M1–M3 retention), reactivation, and high-upside viral referral loops. This is a highly hands-on role requiring deep expertise in CRM and marketing automation platforms to create scalable, "always-on" drivers of MAU and retention.

• Lead Multi-Vertical (MV) Crossover (P0 Focus): This will be your most important contribution. Within the core automation framework, heavily feature and prioritize behavior-triggered crossover loops. Design and test personalized journeys explicitly engineered to transition highly engaged, fuel-only consumers into long-term, high-LTV grocery and restaurant consumers based on geographic proximity and site-level market potential.

• Advanced Personalization Strategy: Infuse deep 1:1 consumer-to-merchant matching and advanced personalization logic into the core communication infrastructure to maximize conversion velocity.

Integrated Incentive Engineering & Optimization

• Harmonize the Incentive Ecosystem: Act as a primary growth steward translating the principles of the consumer habit, incentive, & engagement framework across the lifecycle ecosystem. Ensure our offer and bonus ecosystem functions as a coordinated, unified ecosystem that guides consumers toward long-term habituation.

• Eliminate Subsidization & Drive Efficiency: Partner closely with data science and consumer analytics to isolate true incrementality. Build rigorous control frameworks to deploy strategic bonuses strictly at a consumer’s behavioral "inflection point," ensuring promotional spend is the marginal reason for a consumer’s next transaction.

Martech Collaboration & Platform Optimization

• Support Martech Delivery: Act as a critical cross-functional bridge between consumer strategy, engineering, product, analytics, and data science. Pinch-hit and support the martech projects by clearly scoping and documenting the technical data requirements.

• AI-Enabled Workflow Velocity: Support the deployment and optimization of internal AI-driven lifecycle agents, subagents, knowledge bases, skill bases, and more to accelerate production velocity.

Strategic Influence & Autonomy

• Executive Business Framing: Function as a trusted, high-visibility partner to leadership teams across consumer, product, analytics and executive stakeholders to shape and impact our commercial growth model by turning abstract lifecycle problems into clear strategic roadmaps.

• Autonomous Operation: Be comfortable operating independently while managing projects of extreme complexity and high risk while serving as an expert resource and mentor for the wider lifecycle team.

Competencies You'll Need:

• 8+ years of progressive experience in Lifecycle Marketing and CRM, with a demonstrated track record of increasing consumer engagement and retention within a relevant mobile-first B2C experience, a marketplace brand, or other related industry..

• Bachelor's degree in Marketing, Business Administration, or a related field.

• Deep functional knowledge in marketing engagement platforms such as Braze, Iterable, Salesforce Marketing Cloud, specifically with hands-on experience building and architecting solutions in platforms. This role requires ongoing practitioner-level expertise and comfort personally building, troubleshooting, and optimizing sophisticated automation programs.

• Deep understanding of consumer data analytics platforms, data architecture/pipelines, API connectivity, SQL proficiency, and more.

• Experience developing and optimizing mobile-first lifecycle marketing programs across push notifications, in-app messaging, content cards, and other app-native engagement channels.

• Data-first decision maker with a test-and-learn mindset. Outstanding analytical and critical thinking abilities, and the capacity to interpret data into practical insights and achieve business results.

• A collaborative mindset with a proven ability to build strong, impactful partnerships across diverse teams.

• Excellent communication and presentation skills, with the ability to influence and persuade collaborators at all levels.

Location:

This hybrid role is based in our DC, or NYC office. In-office attendance is required on Monday, Tuesday, and Thursday, and may increase based on project-based needs and changes to Upside’s in-office policy over time.

Compensation:

The U.S. base salary range for this full-time position is $169,000 - $201,000 + equity + benefits. The final starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. Your recruiter can share more about the specific salary range during the hiring process.

#LI-Hybrid
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Benefits:

• Medical, dental, and vision coverage starting on Day 1

• Equity (ISOs)

• 401(k) program

• Family planning programs + paid parental leave

• Physical fitness and wellness memberships

• Emotional and mental health support programs

• Unlimited PTO + 10 paid federal holidays + our annual, week-long Winter Break

• Flexible work environment

• Lunch reimbursement for in-office employees

• Employee Resource Groups

• Learning and Development stipend

• Transparent culture

• Amazing mission!

Diversity and Inclusion:

Diversity drives innovation, and our differences make us stronger. We‘re passionate about building a workplace that represents a variety of backgrounds, skills, and perspectives, and we do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Everyone is welcome here!

If there's anything we can do to support a disability or special need during your application or interview process, please email [email protected].

This email is for accessibility accommodations only, it should not be used to submit job applications.

Notice To Recruiters And Placement Agencies:

This is an in-house search with a dedicated recruiter. Please do not submit resumes to any person or email address at Upside. Upside is not liable for, and will not pay, placement fees for candidates submitted by any party or agency other than its approved recruitment partners.