systems lead


- the low-down -

The Guild is a new hospitality concept that empowers travelers to experience their destination as a local, while enjoying the soft sheets and fancy amenities they've come to expect from a boutique hotel. Think of us as one-part eclectic home, one-part boutique hotel, and one-part college friend who takes you to the secret spots and hidden gems.

Since our March 2016 launch, we've been off to a blistering start. We've raised a few bucks, grown our revenues to a scale unimaginable to most 2-yr-old startups and posted some downright glorious unit economics.

We're proud of the business we've built using only third-party tech. However, this resourcefulness comes with some downsides. Namely, a daisy chain of interconnected systems including a Property Management System (PMS) and Channel manager (CM) which link to various marketplaces: Online Travel Agencies (Expedia, and the Global Distribution System (GDS). On a good day (most days), these systems communicate seamlessly with one another. However, on a bad day, when an issue arises, it affect our most basic business functions.

Regardless of the day, our web of systems makes it difficult to understand our data and surface insights to the relevant business owners. 

- your role -

You'll be the master of our systems and create order from the (occasional) chaos. Furthermore, you'll be expected to extend your subject matter expertise as we build and integrate with the new systems, both off-the-shelf and custom. You'll also translate your intimate knowledge of our systems into beautiful dashboards and reoccurring reports. Think of the roles as equal parts detective, firefighter, and strategic planner.

Although the position is oriented towards systems management and business intel, our lean corporate structure allows (read: forces) you to explore projects spanning many functions, like Marketing, Finance, Operations, etc. In particular, you will work closely with our Product team to influence new systems in development and our Revenue Management team to ensure inventory / prices are in parity across systems.


  • Manage current systems and troubleshoot problems as they arise
  • Optimize our tech-stack by reducing complexity of developing new processes
  • Ensure seamless launch of new properties from a systems perspective
  • Own relationships with key external stakeholders (e.g., 3rd party software vendors, market managers, etc)
  • Support the Product Manager in the development of new systems
  • Track performance / health of the business through the creation of KPI dashboards
  • Support our transition from outdated Excel trackers to cutting-edge data visualization software
  • Contribution to special projects and tasks


  • Ridiculous attention to detail including a spidey-sense for noticing when something is awry in a system
  • Ability to break down problems into their components and test hypotheses in order to quickly diagnose / resolve the issue
  • Rain Man ability to analyze data and find key insights 
  • Strong to exceptionally-strong in Excel. You eat keyboard shortcuts for breakfast, INDEX MATCHES for lunch, pivot tables for dinner, and macros for dessert.
  • Exceptionally organized and self-directed
  • Enjoy charming vendors and partners (by sending gifts including but not limited to: cookies, breakfast platters, wild turkey, and fancy candles)


  • B.S. in accounting, engineering, or similarly technical area
  • Previous experience doing financial / systems auditing, business intelligence, or business analysis 
  • Strong proficiency with a crock pot. Slow roasted poultry dishes preferred, vegan alternatives welcome
  • Your GIF and meme game is strong to very-strong


  • Generous insurance (health, dental, vision)
  • Meaningful equity upside
  • Latest and greatest hardware required to perform your role
  • Free and discounted stays at our well-appointed suites
  • Gratuitous helpings of breakfast tacos and viral videos at the Thursday morning all-hands meeting
  • A spot at our April 2021 NYSE bell ringing ceremony (exact date TBD)

- your team -

We're a group of people who take our work seriously, but never ourselves. We celebrate weirdness, work our asses off, and enjoy the journey. We all wear multiple hats and are working on at least 5 projects at a time. Life is never boring here. We're risk takers. We care about each other and lend helping hands all day, every day. We say no to politics and drama!


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