We are proud to profile a number of our team members spearheading growth and innovation at Roundtrip. Check out the rest of the series to get to know the rest of our leadership team.
Meet Lindsay Tamchin, Roundtrip’s Chief Revenue Officer
Lindsay (Tsai) Tamchin is the Chief Revenue Officer at Roundtrip. She leads all revenue-generating activities at the company including marketing, business development, sales, and account management. Since joining in 2017, she has led the efforts to secure 85+ contracts across the country. Prior to Roundtrip, Lindsay served as the Program Director for Philly Startup Leaders and worked at Deloitte Technology Consulting, helping health systems navigate a rapidly-evolving technology landscape. Her consulting projects spanned developing 3D printing strategies for orthopedic departments to helping the DHHS capitalize on blockchain. She attended the University of Pennsylvania where she received her BSE in Materials Science Engineering and a minor in Engineering Entrepreneurship.
Lindsay, what project at Roundtrip have you worked on that you are most proud of?
I’m proud that we’ve built something that lasts and truly matters. It’s really hard to build a B2B health tech company. A lot of companies launch with huge ambitions, raise a lot of money, and then fade without the durability to navigate the complexity of the healthcare system or improve patient outcomes. From the beginning, we wanted Roundtrip to be different. The goal was to build something impactful and long-lasting that could truly improve how patients access care. Roundtrip has afforded me so many opportunities. I’ve had the chance to build a team and culture from scratch, grow the business to all 50 states, and, most importantly, see real impact on care coordinators and patients nationwide.
One of the parts I’m most proud of is the team we’ve built along the way. We’ve made a conscious effort to hire people who are aligned to our mission, invest in them, and give them real ownership. It’s been incredibly rewarding to teach, mentor, and shape that next generation of operators, and even more rewarding to watch them go on to build their own companies or have successful careers. There’s something special about knowing Roundtrip played a small role in that trajectory.
A favorite memory is a very classic startup moment. We pitched a new customer on a product we hadn’t built yet. Our “demo” was literally a series of InVision prototypes. At the time, it felt scrappy, but looking back, it’s a pretty good reminder of how far we’ve come.
I’m also quite proud of the work we did with the National Institutes of Health to fund a “dose of transportation” for patients seeking treatment for opioid use disorder. This was at a time when the opioid epidemic was colliding with the pandemic, and access to care was even more fragile. That effort led to us being awarded the largest SBIR Phase I grant possible. There’s still not nearly enough academic research in this space, so being able to contribute to that and push the work forward was incredibly meaningful.
What mentor or prominent figure has influenced you in your career and why? You can share more than one.
I am lucky to have a strong community around me, so it’s difficult to point to just one person. However, over the last few years, two of the most meaningful connections have been friends I went to college with who have also pursued careers in health tech. Our regular conversations sit somewhere between mentorship and therapy. There’s something powerful about hearing what other founders and operators are going through in real time. It’s a reminder that you’re not alone in the challenges, ambiguity, or pressure. We share best practices, compare notes, and talk through the kinds of situations that don’t always have a playbook.
They’ve also been strong advocates for me, consistently encouraging me and offering both perspective and honesty when I need it. Particularly as a woman in a male-dominated industry, it’s always great to feel like you have people in your corner, pushing you forward and giving you a dose of confidence or reality when you need it.
Can you share some of your favorite books?
From a career perspective, I always recommend The Last Lecture, Radical Candor, and anything by Jacco van der Kooij. Otherwise, I’m a big fan of the romantasy genre!
What future do you envision for your team at Roundtrip in the next two years?
Over the next few years, we will continue to grow as a connector across the healthcare and transportation ecosystems. Historically, Roundtrip has supported hospitals & health systems optimize what’s within their control: improving workflows, visibility, and outcomes at the point of care. But the reality is that transportation barriers don’t start or end within a single organization. They are the result of misaligned incentives across payers, providers, transportation companies, EMS, and community organizations. To really move the needle, we need to bring those groups together.
For example, Medicaid and Medicare are two of the largest funders of transportation, but reimbursement structures often make it difficult for transportation providers to operate sustainably or staff reliably. At the same time, health systems are feeling the downstream impact in delayed discharges, missed appointments, and strained care teams. Everyone is experiencing the problem and rarely solving it together. It is essential to unify those stakeholders. Not just through technology, but by creating shared visibility, aligned incentives, and a sense of collective ownership over patient access.
Roundtrip is in a unique position because we already work across multiple sides of the ecosystem. The industry must start to operate as a unified front, meaning deeper partnerships, more shared data and insights, and more intentional spaces for collaboration, whether that’s through regional initiatives, customer communities, or broader advocacy efforts. Ultimately, the goal is simple: a system where access to care isn’t dictated by geography, logistics, or fragmented incentives, but by patient need. I believe Roundtrip can play a meaningful role in bringing the right people to the table to make that possible.
Tell me about your hobbies and things you enjoy doing in your free time.
I’m lucky enough to live in Los Angeles, CA with my husband, Holden, and quirky rescue pup, Indy. You’ll often find me on hikes with the both of them, at the beach gladly getting sandy, throwing themed parties, or making PowerPoints for fun.
If you could donate $1million to any organization, what organization would it be?
I’m passionate about causes related to equity and access. I would invest in organizations such as the American Cancer Society, where their Road to Recovery program supports cancer patients who need to get to appointments with volunteer drivers and Undue Medical Debt, who is focused on creating a transparent, equitable and affordable healthcare system where no one delays or avoids care because they fear incurring debt.