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.

Requirements

Your work at Outdoorsy

• Lead and mentor a team of five to seven software engineers, fostering a culture of innovation and continuous improvement
• Manage the team across different platforms and working locations, promoting a collaborative work environment. Some members of the team are located in Europe, with earlier working hours than the US-based developers.
• Identify team members' strengths and development areas, providing regular feedback and coaching to support their professional growth
• Act as an engineering partner to the product manager and designer, contributing to the strategic planning and vision of your team’s projects
• Facilitate open communication between your team and cross-functional partners, ensuring alignment on project objectives, timelines, and deliverables
• Champion agile methodologies within your team, running agile rituals such as grooming, sprint planning, daily stand-ups, pointing, and retrospectives to ensure efficiency
• Continuously evaluate and refine agile processes in collaboration with your team, incorporating feedback to enhance efficiency, productivity, and team satisfaction
• Take accountability for your team's performance, monitoring and reporting on key metrics related to efficiency, productivity, and sprint goals.
• Lead by example in maintaining high standards of code quality, architectural integrity, and user experience
• Implement strategies to mitigate risks, address bottlenecks, and ensure that the team remains on track to achieve its objectives within sprint cycles
• Maintain communication with stakeholders, including updates on project status, insights into the development process, and presentations of milestones
• Encourage a culture of innovation within the team, promoting experimentation with new technologies and approaches that can enhance project outcomes or operational efficiency

What you bring to the table

• A minimum of 5 years in engineering management, with proven experience leading and scaling a distributed team of software engineers
• Demonstrated ability to mentor engineers, fostering professional and technical growth
• Experience in recruiting, hiring, and retaining top engineering talent
• Expert knowledge in agile software development methodologies and the ability to implement and adapt processes that enhance team efficiency and product quality
• Deep understanding of Machine Learning approaches, particularly gradient boosted machines, decision trees, and algorithms relevant to solving matching problems in a marketplace context
• Extensive experience with Elasticsearch, including its implementation, optimization, and maintenance within a high-traffic environment
• Proficient in designing, building, and maintaining services and APIs using Go. Familiarity with additional programming languages is a plus
• Prior experience with two-sided marketplaces at scale, with a strong preference for candidates who have directly contributed to the success of leading companies in the space (e.g., Airbnb, Vrbo)
• A track record of successfully managing projects that improve discovery and search functionalities, enhancing user engagement and satisfaction
• Based in the United States

Benefits

Benefits & Perks:

• Opportunity to help build a company from an early stage
• Competitive salary
• Equity in one of the world's fastest-growing companies
• Comprehensive health and welfare benefits
• 401(k) Match
• Flexible PTO
• Annual RV rentals - we believe in balance and taking the time to nourish mind, body, and soul

The expected compensation range for this position is displayed in accordance with potentially applicable laws. The final agreed-upon compensation is based on a number of factors, including but not limited to: individual education, qualifications, prior work experience, and geographic work location. The total annual compensation package may consist of a base salary and bonus dependent upon position.

It is the policy of Outdoorsy Holdings, Inc. to provide equal employment opportunities without regard to race, color, religion, sex, national origin, age, disability, marital status, veteran status, sexual orientation, genetic information or any other protected characteristic under applicable law. This policy relates to all phases of employment, including, but not limited to, recruiting, employment, placement, promotion, transfer, demotion, reduction of workforce and termination, rates of pay or other forms of compensation, selection for training, the use of all facilities, and participation in all company-sponsored employee activities. 

We continue to have our home and headquarters in Austin, Texas, but we have embraced a distributed model of working to reach the best talent in the United States and globally. While some roles may require proximity to our Austin office or one of our properties, roles based outside of our Austin office can sit in any of the following 21 US states: AR, AZ, CA, CO, FL, GA, IL, IN, MN, MO, MT, NV, OH, OK, SD, TN, TX, UT, VA, WA and WV. Please only apply if you are able to live and work full-time in one of the states listed above. State locations and specifics are subject to change as our hiring requirements shift.