Upside Business Travel

Principal Product Manager, Personalization

Upside Business Travel$224K — $243K *
Consumer Technology
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 10+ years of product management experience in complex or platform-level initiatives.
  • Proven experience building scalable personalization platforms or CRM systems.
  • Strong quantitative skills for data-driven product decisions and experimentation.
  • Technical fluency to convey detailed information into strategic insights.
  • Exceptional communication skills to influence stakeholders without direct authority.
  • Strong business acumen connecting product decisions to company strategy.
  • Deep understanding of consumer behavior and motivations.

Responsibilities

  • Own the strategy and roadmap for the personalized growth engine.
  • Define requirements and prioritize the backlog across various growth components.
  • Establish success metrics and KPIs, using data for guidance.
  • Drive multi-vertical network adoption through targeted localized communications.
  • Conduct rapid experimentation on messaging and incentives for repeatable habits.
  • Collaborate with consumer marketing to translate their needs into product requirements.
  • Lead cross-functional alignment among engineering, design, data, and marketing teams.

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 + annual Winter Break
  • Flexible work environment
  • Lunch reimbursement for in-office employees
  • Employee Resource Groups
  • Learning and Development stipend
  • Transparent culture
  • Amazing mission!
Full Job Description
The Impact You'll Make

Upside is building a sophisticated, personalized engagement system that uses AI, marketing technology, and consumer data to bring users to the Upside app with the right message, creative, and incentive at the right moment to drive the next highest action for the consumer. This is one of Upside's highest-leverage growth opportunities, with the potential to meaningfully grow user acquisition, frequency, retention, and revenue. As the Principal Product Manager owning this space, you'll have the rare chance to build this system largely from the ground up - turning an ambitious, high-level vision into a concrete, sequenced roadmap, and making foundational calls about the systems, partnerships, and technology needed to bring it to life.

What You'll Do
  • Own the strategy and roadmap for building Upside personalized growth engine. Translating a broad, ambitious personalization vision into sequential, buildable phases.
  • Define clear requirements and specs, and prioritize the backlog across the growth stack - data infrastructure, multi-channel outreach, app surface areas, creative personalization, and incentive systems - including build-vs-buy-vs-integrate decisions.
  • Define success metrics and KPIs for the growth system, and use data to guide prioritization and validate impact.
  • Lead efforts to drive multi-vertical (Fuel, Grocery, Restaurant) network adoption, identifying high-relevance users and targeting them with localized, personalized communications based on proximity to relevant retail locations.
  • Run rapid experimentation on messaging and incentives, using results to identify what drives repeatable user habits before scaling successful patterns globally.
  • Build a strong partnership with Upside's internal consumer marketing team, deeply understanding their needs and translating them into clear product requirements.
  • Lead cross-functionally without direct authority, aligning engineering, design, data, and marketing around a shared roadmap and set of priorities.


Competencies You'll Need
  • 10+ years of product management experience, including leading complex, ambiguous, or platform-level initiatives.
  • Proven track record of building scalable personalization platforms, CRM systems, or 0-to-1 products - not just isolated features.
  • Strong quantitative and analytical skills, with hands-on experience using data and experimentation to guide product decisions.
  • Technical fluency and ability to synthesize granular detail into clear, strategic narratives for different audiences - comfort operating at both a high strategic level and a deep analytical level is critical to this role.
  • Exceptional communicator who builds deep cross-functional trust and can influence senior stakeholders without direct authority.
  • Strong business acumen, with the ability to connect product decisions to retention, revenue, and broader company strategy.
  • Deep consumer empathy and an intuitive understanding of what motivates user behavior.


Location:

This hybrid role is based in our Austin, Chicago, 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 varies by work location:
  • Tier 1: NYC $224,000 - $243,000
  • Tier 2: Austin, Chicago, Washington, DC $204,000 - $221,000

In addition to base salary, this position is also eligible for equity and 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 for your location during the hiring process.

#LI-Hybrid
#LI-CO1

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!

About Upside Business Travel

Upside Business Travel is a travel management company that offers a platform for booking business travel. The company was founded in 2015 by Jay Walker, the founder of Priceline.com. Upside Business Travel's platform allows users to book flights, hotels, and rental cars in one place. The company also offers a rewards program that gives users gift cards for booking travel. Upside Business Travel has raised over $50 million in funding.
Learn more about Upside Business Travel
Size
100 employees
Industry
Founded
2018

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