Head of Digital Product and Software Engineering at Getaway

| Greater NYC Area
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Getaway provides simple escapes to tiny cabins nestled in nature for stressed out folks where they can recharge and disconnect. Our experiences are more than the beautiful tiny cabins nestled in the woods—it’s about disconnecting and living in the present moment. It’s about learning to disconnect from your cell phone and rediscovering the art of a good conversation. It’s about tuning out the endless noise of society today and listening to the great outdoors.  Outposts are located within a two-hour drive of major metro cities—far enough to disconnect but close enough for a spontaneous escape. 

The Head of Digital Product and Software Engineering will oversee our front end website (where 100% of Getaway bookings are made), our proprietary booking engine, our proprietary property management system and various other custom back-end tools and third party integrations. We are looking for someone who is incredibly good at prioritizing projects, developing specs, generating buy-in within and across departments, and of course getting good tech built and maintaining it well. This person should be versed in making compelling analyses with buy-vs-build decisions and generally have a deep understanding of both technology and business.

This role will oversee our engineering team which is currently three engineers and a handful of freelancers. Therefore, it is important that this person has successfully managed engineering before. 


  • Define and own the product roadmap, taking product from conception to launch. 

  • Be a leader to the tech team and within the company, cooperating with teams across the organization to clearly communicate product directions, plans, risks, trade-offs, and opportunities. 

  • Set clear goals and deadlines and take responsibility to meet them 

  • Develop a deep understanding of user behavior, metrics, and look for ways to drive key product goals. Customer needs and requests will help inform new value propositions. 

  • Be a thought leader for how tech can shape the strategic direction of our business and unlock more growth 


  • 5+ years of product management experience at a company (or companies) that deliver popular consumer facing products. 

  • Experience managing a product and engineering team.

  • Ability to code is a plus, familiarity, curiosity and management of engineers is a must. 

  • Strong business acumen - You can look at things holistically, prioritize and make decisions that push towards top line company goals. 

  • Excellent analytical and quantitative skills with a focus on data-driven decision making. You know how to dig into a database and pull what you need when you need it. 

  • Know how to use data to inform sound product decisions (SQL proficiency preferred) 

  • Experience working in a venture backed startup or high growth company. You embrace a startup's agility, speed, working under pressure, and ability to handle ambiguity with grace are must-haves for this position. 

  • The ability (and desire) to both strategize and execute. 


Location: The position is based at our HQ in downtown Brooklyn. Perks include working with a genuinely good group of people, 20 days mandatory vacation (you get in trouble if you don't take your time off!), one Friday off a month, and medical/dental/vision. 

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