Senior Manager of Learning & Development

Job Description

Your job is to oversee the creation and execution of all training initiatives for our hotel team members so they can, in turn, deliver the exceptional service our guests, partners, and vendors have come to expect. Once you have nailed doing this for our hotel staff, your scope will expand to ensuring all of our corporate staff also have the learning and development they need to be highly successful in their roles, too.

You built the training engine that allowed us to seamlessly open multiple hotels at once across the country. Because of your leadership and L&D expertise, we know all of our new hotel team members are fully equipped to serve our guests at the highest level and run world-class hotels. As a result of your training program we brought the best out of our team, disrupted both the real estate and hospitality sectors and became a billion dollar company.

As you get started in the role:

  • Conduct a training needs assessment to determine everything our hotel team members (everyone from an hourly Guest Experience Associate up to a General Manager) need to know in order to be successful in their role. This will involve a listening tour where you speak to our VPs of Operations, hotel team members at every level, and functional experts across our company to understand what has worked well and hasn’t in terms of training to-date. You’ll also need to review all SOPs and training materials that currently exist.
  • Develop a detailed training plan for standardized and individualized training at each of our hotels. Your plan will include when various training components need to be delivered to hotel team members based on open dates and should be developed with a ‘waterfall approach’ (you train the hotel’s GM first, who then owns training his/her team).


  • Serve as an instructional designer who will be responsible for creating some of the content and also facilitate more of it as you continue to develop your knowledge and awareness around our systems and operational processes.
  • Communicate and coordinate with all trainers (functional experts) across the organization to ensure they know what they need to train on and what’s expected of them in terms of their in-person delivery. Share facilitation best practices with them and coach them after they train to help them improve (video tape sessions and watch them with facilitators to improve curriculum and delivery).
  • Coordinate all training on site to ensure it goes smoothly and feels unified (similar formatting, delivery, etc…). You will be at each hotel for at least a week before it opens.
  • Become a WhyHotel training expert and, with time, deliver more of it yourself. As your role evolves, the functional experts will provide you with the content and you will transform it into a roll-out ready training program that you own.
  • Continuously improve your training as you go by surveying both new hotel employees and also those with longer to tenure to understand what worked well and what you need to change with your next training. Review guest reviews to determine what training should be reinforced and what additional training is needed.
  • Create detailed and more specific training to address specific scenarios that arise. This will involve revisiting properties as needed to reinforce what has already been learned (did it truly “stick”?) and diving deeply into site or role specific issues that surface.


Job Requirements


  • 5+ years of Learning & Development experience. Specifically experience with training assessment, development, deployment, and improvement.
    • Experience with and knowledge of adult learning and training procedures.
    • eLearning experience preferred - eventually, we’ll need to leverage technology more heavily to deliver training as the number of our hotels grow.
  • Strong Project Management skills. You excel at building detailed training plans that can be adjusted easily when timelines change on a dime. Your plans leave no stone unturned and cover every nitty gritty detail.
  • Passion for stakeholder engagement. You love to sit at the center of engaging with multiple people to ensure they all have what they need to pull together and create a sum that is greater than it parts. You have thrived in positions where you’ve played the role of “central casting” - coordinating lots of different people and pieces.
  • Obsession for ensuring people have the tools and resources to do their jobs well. You love ensuring that people at work have everything they need to do their jobs to the fullest. You enable others you work with to become better versions of themselves by coaching and supporting them with your awesome facilitation ‘tips & tricks’.
  • Superb communication. You are effectively and efficiently able to communicate lots of nitty gritty detail with your fellow team members (whether hourly team members or executive leadership) and management in a highly dynamic and rapidly evolving environment. You respect others’ time (knowing training is NOT their full-time job) and give them as much advance notice as possible so they can facilitate with ease, in a meaningful way.
  • Able to maintain the speed required for WhyHotel to grow while balancing the quality of the thoughtful learning experiences you deliver. You are a dynamic and highly adaptable leader who won’t see two weeks’ worth of work as time wasted when plans change.
  • You lead by example. You are a hands-on leader who supports your team, develops them and helps them see their full potential.
  • You hear and see yourself in our core values. You can relate to them and are excited to live by them.

Salary: Commensurate with experience - please be sure to tell us your salary expectations in the application questions.
Equity: All full-time employees are eligible for stock option grants upon joining our team and thereafter annually.
Benefits and Perks: We offer medical, dental, and vision coverage. You’re eligible to participate in our 401(k) after your first 6 months with us and we match up to 100% of every dollar you contribute to our 401(k) up to 4%. We’ll reimburse you $75/monthly for your cell phone or give you a new one.
Location: You will work out of our corporate headquarters in Washington, DC.
Manager: You will report directly to Heather Schwager, VP of People Experience.
Team Beats Individual: We are all in this together. We hold all team members responsible for bringing talent to our organization and guests to our hotels. After all, it’s the only way we’re going to grow!
Answers to Your Questions:  We have hopefully anticipated and answered many of your questions in our Candidate Insider Playbook. Please review before applying.

At WhyHotel, we don’t just accept difference – we celebrate it, we support it and we thrive on it for the benefit of our team, our work and our community. WhyHotel is proud to be an equal opportunity workplace.

Additional Details

Date posted: 01/22/2020

Salary: TBD

Location: Washington, DC

Start Date: 02/01/2020

Contact: Cate Lyle

Phone: ------


Apply Online:

Prefer: online

Company Name: WhyHotel


WHAT IS WHYHOTEL?WhyHotel is a venture-capital backed, DC-based startup that operates "turn-key, pop-up hotels" in newly built, vacant luxury apartments during their lease-up phase. Blurring the line between hospitality and home, our model provides the value and space of a home-share with the consistency of a luxury hotel. Thanks to WhyHotel, real estate developers now have a new way to leverage vacant units during lease-up and you have a new way to travel. In addition, our new business arm, Hospitality Living, will deliver the first of its kind ground-up, flexible use buildings, targeted to launch in 2022. For more details on WhyHotel and our hiring process, please read our Candidate Insider Playbook.