What inspired you to start RubyWell? How did your experiences caring for your Grandmothers and best friend influence the vision for the company?

Prior to moving into US-based healthcare, I was fortunate enough to join my family (biological and found) in providing care to my grandmothers and to a friend. I never saw it as a role or a job, and I was fortunate enough to have a lot of support. But time spent with people I loved at the end of life showed me how little systemic support family caregivers have, and how few resources many of them can draw on. It can be one of the most rewarding experiences of a life, but it can also be isolating, emotionally, and financially draining.

I was born and raised in Canada, where my grandmothers had different options than families in the US do. Later, working at an early-stage Medicare technology company, I looked closely at how the country’s rapidly aging population manages care at home, sometimes by choice and often by necessity. Combined with my own experience, it left me asking what was missing.

You’ve held leadership roles across mission-driven nonprofits, healthcare technology, and value-based care. Looking back, what lessons from those experiences have most influenced the way you approach building RubyWell today?

Over the course of my career I’ve worked with great leaders and great teammates. I’ve learned that being able to clearly define the problem that you want to tackle is the first critical step in arriving at product design that gets to the deepest pain points. The question cannot just be “caregiving”, or, “how do we support caregivers?”, but rather a problem definition with clearly defined outcomes that would help us as a company better identify whether we were arriving at a sustainable solution. The challenge that we wanted to address when we set out to build RubyWell was the following: how can one build a solution that compensates family caregivers caring for a loved one on Medicare, without requiring any changes in legislation or policy?

Medicare doesn’t cover day-to-day care at home. Its home health benefits are prescribed based on medical need, and even those are underused and unevenly delivered. So the resources to support these families have to come either from the system as it is or from the financial outcomes that family engagement generates, tracked and proven in a way that hasn’t been done before.

- Healthcare is often described as fragmented. What has been the biggest challenge in building a solution that works across providers and families?

RubyWell’s model is based on a simple observation: many beneficiaries receive clinically appropriate care plans, disease guidance, and preventive recommendation. But these plans frequently fall apart in the home between episodes of care. Family caregivers are closest to this daily reality. However, current care delivery systems have limited infrastructure to identify appropriate caregivers, train them in shared operational language, connect them to escalation pathways, measure which of their activities improve outcomes, or pay them for their work. Proving the economic value of caregivers, in a quantifiable way that health systems trust, is central to a solution that works across providers. Because health workers are in chronically short supply and there is no standard compensation model for caregivers, families have lacked both pay and trusted human support. Any solution has to create measurable financial value for the health system while meeting families’ needs.

There are many fragmentations across healthcare, and a caregiver solution won’t address all of them. However, RubyWell’s product design turns everyday engagement into a structured, longitudinal record of the home that is captured and turned into data that can be shared into the patient’s electronic health record. It also allows for care navigators to supervise that engagement, and the resulting documentation drives caregiver compensation.

Much of healthcare is designed around interactions with clinicians, yet most care happens at home. Why do you think the healthcare system has struggled to recognize and support the people doing that work every day?

Integrating family caregivers into the healthcare system is hard for a few reasons. The caregiver isn’t the customer, so clinical interactions haven’t historically captured information about them, which makes them hard to identify. We also need to confirm with the patient that the person who identifies as their caregiver is the person they want in that role. Caregivers aren’t formal members of the care team: they are technically untrained, have no defined pathways of engagement, and their work isn’t quantified, so oftentimes they remain invisible.

RubyWell makes caregiver activity visible and measurable, by action and by dosage. Caregivers are identified, their role is validated by the patient, and they agree to training and long-term engagement. That makes it possible to overlay household data on claims data to predict adverse events, and to document the outcomes of healthcare values. Aligning systems incentives with families’ needs make a systemic solution more likely.

As more care shifts into the home, what role do you see family caregivers playing in the future of healthcare, and what is your long-term vision for RubyWell?

Our goal isn’t to replace clinicians or formal care delivery. It’s to reinforce execution of existing care plans at home, and to generate evidence on which caregiver-supported activities, at what dosage, improve outcomes over time.

Health plans and care management organizations struggle with engagement. The people who most need help are often the hardest to reach. Phone outreach hits voicemail, and remote monitoring produces data without context, so the home, where chronic disease is actually managed, stays largely invisible. Care plans often fail not for lack of good medical guidance but because execution at home breaks down. Medication adherence slips, mobility goals are dropped, appointments are missed, and warning signs are noticed too late. Between clinical encounters, small problems compound into preventable ED visits and hospitalizations. As more older adults age at home and workforce shortages grow, this will only intensify.

Millions of family caregivers already invisibly provide daily support. Because they’re organized around the person rather than a single condition, they notice changes in function, mobility, appetite, mood, or cognition long before they become acute events. With training and support from care navigators partnered with clinical organizations, they become more effective at carrying out whole person care goals while reducing costs for the system.

What led you to GAIN? What has been the highlight of your experience working with GAIN investors? How has GAIN influenced your alumni experience?

GAIN invested in my previous company where I was a founding member, so it felt natural to reconnect with them when I left to start RubyWell. This reconnection led me to other engagement opportunities with the University as a whole. I recently joined an on-campus panel of Hoya alumni working in the caregiving space which was my first time back to Georgetown in many years.

As this is being sent to other Hoyas, can you please share with us a little about your time at Georgetown and how it helped shape you as a founder/start-up operator?

I was a coxswain for the men’s heavyweight crew during my time at Georgetown, and we won nationals in the coxed four. The intensive training, focus and discipline that a varsity sport requires, along with coaching from incredible people like Tony Johnson, created a foundational understanding for me of competition and how to take thoughtful, strategic chances in the world.

Thinking back on your Georgetown experience, can you speak to how classes, friends, clubs, etc influenced your entrepreneurial journey?

In addition to my coxing, I also had a very close group of friends who were my roommates, and who are still very close today. Each has made her way in the world on a different path, which showed me that success takes many forms. From them, from rowing, and all of my decisions at school, I learned to gauge risk and use it to reach things that would otherwise have been out of reach. That began the year after I graduated, when I founded DC SCORES, which later became America SCORES.

If you could give a piece of advice to a Hoyapreneur or aspiring Hoyapreneur, what would it be?

There is a great book called Against the Gods: The Remarkable Story of Risk by Peter L. Bernstein. I didn’t read it until a bit later in my journey, but understanding and believing in the value of taking risks has been one of the most important lessons of my life.