Chief of Staff

Austin, TX
Apr 19, 2021
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This is truly an opportunity to build something from the ground up, and we're looking for a swiss army knife to come along for the ride. Must be okay with: ambiguity, uncertainty, experimenting and learning. To apply for the job, please email See instructions below.

The Problem There are 48M people over 65 and that number is doubling over the next 25 years. In addition we've got the average life span increasing from 74 to 93 years old. 70% of people over 65 will need what's called Long Term Care, which is help with things like bathing, medication management, meal prep, dressing, etc. It's non medical, and it is not covered by insurance. The cost of 4 hours of personal, non medical care every day costs someone upwards of $2,400 per month.

About the Company Homestay is a vc-backed senior housing startup reinventing how care is delivered at home. We turn residential houses in to shared homes for 2-4 people. For individuals who are independent but need light to moderate help, Homestay is the most affordable and flexible way to remain in a home. By expertly matching 2-4 individuals together as housemates, we enable seniors to reduce their cost of care by 60%-75%.

The Role We are hiring an executive to lead the company strategy for growth, financing, and operations. Over time, you will be tacking hairy, intellectually interesting questions:

  1. Where are we exposed from a risk perspective? How do we structure the company to mitigate risk? How do we structure insurance? How do our finance systems mirror insurance and liabilities. You will work across finance and legal to lead the strategy. This is a critical piece of the puzzle to be able to scale.
  2. How should we leverage debt and equity to scale? How does this impact our financing strategy?
  3. Understand why no one has ever scaled beyond 10 residential care homes, and identify key processes, systems, and compensation policies we should put in place to address these blockers.
  4. How do we create the best jobs for caregivers? What benefits can we offer? What are the best ways of retaining staff? How do we balance margins with retention? What is the sweet spot?
  5. Hiring great care home managers (the person who runs the household and oversees staffing, house ops, and is the point person to families) is key to scale. What is the right incentive structure to incentivize care home managers to operate with an owner/operator mindset?
  6. Oversee finance function. This is critical to demonstrate that the processes and systems in place are repeatable In the first 3 months you will

1. Help stand the first house up. This will include: working with our homecare partner to set up care needs.Coordinate with furniture vendors to make sure furniture is delivered. You might be assembling furniture or finding a task rabbit to help install a ceiling fan. 2. Finance. Setting up banking details for the op co that will operate the home. Writing a lease agreement between the op co and the house. 3. Risk. Choose our Professional & Liability insurance policy. 4. Create marketing collateral, drop collateral at local hospitals, meet discharge planners. 5. Figure out an efficient way of giving community associate money every week to manage the house (buy groceries, supplies) using technology. Today this is done by handing the associate cash and asking for receipts. 6. Build an operating model for the homestay home, test different models and variables to answer key strategic questions.


  1. Self starter. The CEO is not a hands on manager and would love someone who excels at managing upwards, is super organized, and takes initiative to define and execute her/his job.

  2. Resourcefulness. We need a permit but the fire marshal is telling us we need a big water tank on our backyard that we don't need. How do we prove that it is not required? I know! Lets get a drone and fly it over all the other care homes and prove that they were not required to do what he's asking us to do. Stuff like this.

  3. Good attitude. Nothing I (the CEO) do is sexy on a day-to-day basis. This is hairy work. We're caring for seniors who are incontinent, who need help bathing, who may not remember who we are. I spend time at the post office, or getting quotes from bath remodelers, or meeting with assisted living operators who could partner with us.

  4. Work ethic. I would love to work with someone who derives fulfillment through work and how they impact others lives. If you are motivated to work long hours because you believe in what you're doing, that is really important because we work whether its a Saturday or a Monday, if something needs to get done it's done.

  5. Organized. I would love someone to keep us on track - setting our weekly rhthm, managing the team, keeping the ship going. Apply Please email the founder at with answers to the following:

  6. Tell me about yourself

  7. Why are you interested in this role? Please share linked in profile.

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