Engineering Manager

About Outdoorsy

Since 2015, Outdoorsy Holdings has pioneered access to the outdoors by creating the world's leading outdoor travel ecosystem. Millions of guests trust Outdoorsy to help them create lifelong family memories and partners rely on their products and innovations to grow their businesses and provide life changing sources of revenue. 

Outdoorsy's businesses include Outdoorsy.com, the largest outdoor travel and hospitality marketplace; the Outdoorsy Destination Network, a portfolio of campgrounds and glamping retreats in the backyard of our nation's most beautiful landscapes; Roamly, its proprietary insurtech that underpins Outdoorsy and serves as a transformative insurance platform to power global marketplaces. 

At Outdoorsy, we are driven by a profound commitment to reconnect people with nature and foster deeper interpersonal connections. 2023 marked a milestone for us as we achieved profitability, and we are currently experiencing a robust multi-year growth rate of 175%. In 2024, we anticipate surpassing $3 billion in transactions. Our success story includes celebrating over 1 million trips and more than 7 million booked travel days as of June. Roamly's growth trajectory is equally impressive, boasting an annual increase of over 100% and accumulating over $54 million in written premiums on its platform. The recent launch of Roamly RAC™, our open API platform, is set to revolutionize the market. It offers a comprehensive digital insurance suite for marketplaces, enterprises, and dealerships in the RV and boating sectors, as well as insurance carriers looking to cater to consumer markets with advanced digital solutions.

Outdoorsy's businesses are united by a long-term mission to restore our relationship with the outdoors, and each other.

About You

You are an experienced engineering manager with a passion for technology and innovation, especially within the context of travel and exploration. With a solid background in engineering, you're not just adept at leading and nurturing a team of software engineers; you're also hands-on and willing to dive deep into code to drive projects to completion. Your leadership style is characterized by empathy, transparency, and a drive to foster professional and technical growth among your team members.

Your engineering expertise is complemented by an understanding of the dynamics of two-sided marketplaces in the travel industry. This insight, coupled with your experience in developing compelling discovery features, positions you perfectly to improve user engagement and contribute to our growth. You have a track record of exceeding user expectations by delivering innovative and intuitive travel-focused digital products. Ideally this is not your first marketplace or travel company and you have knowledge of the unique challenges faced by others like Airbnb, Vrbo, and more.

At Outdoorsy, you will spearhead the efforts to refine and expand our platform's "front door," leading a distributed team of engineers. This team shares a unified goal: to grow Outdoorsy's reach and to introduce our users to new travel experiences. In addition to technical leadership, your role involves strategic thinking, as you'll be working closely with your team’s product manager and designer to introduce groundbreaking products that lead the industry in outdoor travel.

Your enthusiasm for crafting exceptional products and your strategic skills in navigating the challenges of the travel marketplace will be instrumental in driving Outdoorsy's efficiencies and growth. Among other areas, you will improve our nascent search effort, strategize how ML/AI could fit into our strategy, and unwind legacy match systems that use gradient boosted machines and decision trees. You will grow and nurture young technical leads who are trying to figure out what being a manager is about within the organization. Your contributions will not only shape the future of our platform but also inspire a culture of innovation and excellence within our team.