VP of Product



Remote (USA timezones)

About the role:

As VP of Product, you will be responsible for collaborating with the Leadership Team to establish the product vision and strategy that helps us achieve the company vision. You will lead and mentor the growing team of product managers, product designers, and researchers to ensure they're progressing in their careers, developing incredible products for our members, and driving results for the business.

You will be developing and refining processes for the Product Team while aligning and collaborating across all functions. Additionally, you will ensure that we are always shipping engaging, delightful, simple, and high-impact product experiences that empower millions of people to travel and experience the world. You will be a part of the Scott's Cheap Flights Leadership Team and will report directly to the CEO.

In the short term, you will:

  • Lead, mentor, manage, and continue to build a world-class product organization that demonstrates an exceptional drive for growth, member obsession, and the long term vision for the product
  • Gain a deep understanding of the company vision, OKRs, product, competitors, industry trends, data, and research
  • Collaborate with the Leadership Team to further define, communicate, and evangelize the product vision, strategy, and initiatives
  • Continue to develop our culture of continual improvement, innovation, inclusivity, growth, and collaboration
  • Empower product managers, engineers, and designers to solve challenging problems that deliver value to our members
  • Build upon our foundation of deep airfare and travel knowledge to create an automated and personalized experience for our members
  • Develop understanding and empathy for our current and future members by reading feedback, analyzing data, and conducting member interviews
  • Establish healthy and collaborative partnerships with other functions and individuals throughout the company

In the long term, you will:

  • Develop a world-class consumer product experience for millions of travelers around the globe that helps them travel and experience the world
  • Own the product vision and strategy that gets the business to $100M+ ARR in the next 3-5 years
  • Proactively steer the product experience toward new markets and product lines that align with our vision and brand
  • Be a fantastic leader, manager, and coach that sets clear goals, empowers team members, gives thoughtful feedback, and further establishes our culture of inclusivity and collaboration
  • Help build a leading consumer tech company and brand in the travel industry that consistently attracts new employees that are talented, driven, and excited about what we're building
  • Develop a deep knowledge of our members, airfare & travel, target markets, competitors, and industry trends

What you bring to the table:

  • Consumer Experience: You have 8-10+ years of experience building consumer-facing products. You have a deep appreciation for building a fantastic brand along with an intuitive, beautiful, and useful user experience.
  • Team Leadership & Management: You have at least 5+ years of experience leading highly capable product teams, with demonstrated success hiring, developing, and mentoring a team of product managers and product designers, ideally in a distributed environment. You provide individualized and thoughtful feedback, coaching, and development opportunities.
  • Track Record of Growth: You have a proven track record of significantly scaling a growth-stage B2C company to $50M-100M+. You have an understanding of growth loops, the importance of the new member experience, and how product-led growth can help the company scale.
  • SaaS Metrics Understanding: You understand annual recurring revenue (ARR), net revenue retention (NRR), and LTV/CAC. You can analyze cohorts and help guide the team to build products that inflect leading indicators that drive these metrics.
  • Problems, Not Features: You empower the product managers, designers, and engineers to creatively solve challenging problems with design and technology. You spend time understanding and solving problems, not creating features for the product managers to build.
  • Remote-First: You are excited about the future of remote work and interested in testing and using new processes, tools, and ways of working that enable employees to work from anywhere while consistently producing fantastic work. You are less interested in when someone is working and more interested in the outcomes they produce. You are excited by the idea of helping make this a leading remote company to work for.
  • Visionary, Innovative, & Strategic: You have a track record of not only optimizing existing product lines but building new, revenue-generating product lines from the ground up that drive the business forward. You can identify and champion "blue sky" product opportunities while still remaining true to our brand and our members.
  • Member-Focus: You understand, empathize with, and value our current and future members. You see them as people and customers, not simply as "users" or data points on a dashboard. You care deeply about building great products for people while driving results for the business.
  • Discovery, Research, Data, Testing, & Iteration: You have a proven ability to develop, execute, teach, and scale a disciplined product development process.
  • Automation & Personalization: You have experience building technology that scales through automation and can provide customers with a fantastic personalized experience.
  • Leadership Team Experience: You have previous experience as a member of a leadership team, driving strategic decisions and collaborating cross-functionally. You understand the need for healthy debate and thrive in a feedback-driven environment.

Must have's:

  • Ability to travel four times per year: twice for Leadership Team off sites and twice for full-company retreats
  • You must be legally authorized to work in the United States

Nice to have's:

  • Mobile experience
  • International market experience
  • Social & community experience
  • Experience working within the travel industry

Why you might love working here:

  • 100% remote work environment
  • Competitive salary and equity compensation
  • Open vacation policy, with a 3-week minimum!
  • Comprehensive health, vision, and dental insurance
  • 401(k) with a 5% match
  • Up to 12-weeks of paid family leave
  • Continuing education & development reimbursement
  • Two company retreats per year (we recently went to Cabo!)
  • Challenging problems to solve and an awesome team to collaborate with every single day

We want you to bring your authentic self to work every single day. We accept you for who you are and consider everyone on an equal opportunity basis without regard to ancestry; age; appearance; color; gender identity and/or expression; genetics; family or parental status; marital, civil union, or domestic partnership status; mental, physical, or sensory disability; national, social or ethnic origin; past or present military service; sexual orientation; socioeconomic status; race; religion or belief.‍

‍If you require a reasonable accommodation or assistance for any part of the interview and employment process, please contact us at and let us know the nature of your request.