Pear Healthcare Playbook

Welcome back to the Pear Healthcare Playbook!Today we’re excited to sit down with Jeffery Liu, Co-Founder and Co-CEO of Assort Health, a company building specialty-specific AI voice agents to fix the front door of healthcare. Assort is reimagining patient access by reducing hold times, improving scheduling, and helping patients get to the right care faster.In this episode, we explore how Assort got started, why patient access has remained such a stubborn problem in healthcare, and what the team learned from shipping its earliest real-world deployments. We dive into why specialty-specific workflows matter, how Assort thinks about encoding the complexity of scheduling and triage, and what it takes to turn highly customized implementations into a scalable platform. We also discuss the company’s broader vision for AI-powered patient navigation across voice, text, and other channels.

Othman Laraki, co-founder and CEO of Color Health and former product lead at Google and Twitter, discusses reinventing cancer care with a virtual-first, end-to-end model. He explains how reducing friction across screening and follow-up drives uptake. They cover translating tech playbooks to healthcare, system-level solutions like lung CT screening, and cautious AI use to expand clinical access.

Today we're thrilled to get to know Travis Zack, Chief Medical Officer of OpenEvidence. OpenEvidence is the world's leading medical information platform and the fastest growing applications for physicians in history. Over 40% of US clinicians leverage OpenEvidence for evidence based practice support that is directly embedded into their workflows.Through an array of strategic content partnerships (including the American Medical Association, The New England Journal of Medicine, The Journal of the American Medical Association, and all eleven JAMA specialty journals—such as JAMA Oncology and JAMA Neurology) OpenEvidence gives clinicians the power to search once, skip the scavenger hunt, and surface the science in seconds. Most recently, OpenEvidence has raised $200M in its Series C from Top Investors like Sequoia, GV Thrive, Kleiner Perkins and others!In this episode, we discuss how OpenEvidence is transforming access to medical evidence, the company’s rapid growth and adoption by clinicians, its business model and journal partnerships, and the future roadmap for AI-powered clinical decision support.

Welcome back to the Pear Healthcare Playbook! Every week, we’ll be getting to know trailblazing healthcare leaders and diving into building a digital health business from 0 to 1.We would greatly appreciate if you took a moment to listen to the episode on either Apple or Spotify and leave us a rating! Your support helps our guests' insights reach a larger audience!Today we're grateful to get to know Amar Kendale,  Co-founder and President of Homeward, a company reinventing how care is delivered in rural America. Amar has spent the last 20 years building healthcare products that make life better for patients, providers, and health plans. At Homeward he is focused on improving access to care in rural communities. Before that, he helped grow Livongo from an early-stage startup to its $18B acquisition by Teladoc, where he became Chief Product Officer.In this episode, we’re diving into how Homeward started, the challenges in building in rural health, how Homeward operates and gets paid, and how the company hopes to scale and navigate the upcoming year. 

Today, we’re excited to get to know Adam Stansell, CEO and Founder of Axle Health, the operating system for Home Health.Before founding Axle, Adam spearheaded the launch of new markets at UberEats and built a high-growth business line at Motive, a leader in fleet logistics. With deep expertise at the intersection of operations, technology, and scale, he’s now bringing world class logistics to one of healthcare’s most overlooked frontiers: home health.Founded in 2020, Axle is tackling the $150B+ home health industry in the US growing at 9% every year, of which most of home health still runs on old legacy software or spreadsheets. Recently announced, Axle has raised $10M in Series A led by Carl Byers and Julia McDowell at F-Prime Capital, joined by Lightbank and previous investors YC and us at Pear VC! We at Pear, especially my GP Mar Hershenson and I have been super grateful to be part of his journey.

Chris Ellis, CEO and Co-Founder of Thatch, brings his expertise in cancer research and clinical software to the forefront of modernizing health benefits. He shares his personal journey shaped by loss and the transition from research to entrepreneurship. The discussion unveils the complexities of launching consumer-centric healthcare solutions, the importance of collaboration in health tech, and strategies to navigate policy impacts. Ellis emphasizes resilience in entrepreneurship, sharing how setbacks can drive growth and innovation in a challenging industry.

Today, we’re excited to feature Michelle Davey, CEO of Wheel. Wheel is redefining virtual care by connecting clinicians to telehealth opportunities and equipping healthcare organizations with scalable, tech-enabled solutions. Under Michelle’s leadership, the company has become a leading platform expanding access to care nationwide. Before Wheel, Michelle brought together experience from Google, Favor Delivery, and Medtronic—insight that now helps shape her vision for the future of care delivery.In this episode, we dive into how Wheel is powering virtual care infrastructure for enterprise healthcare, the strategic thinking behind acquiring GoodRx’s virtual care platform, how Michelle sees the future of telehealth evolving across consumer and pharma markets, and what founders should consider when navigating M&A in digital health.

Today, we’re excited to get to know Dr. Ali Khan, Chief Medical Officer of Aetna Medicare, overseeing healthcare services for over 4 million members. His career spans across some of the most impactful value-based care organizations, including Oak Street Health, CareMore, and Iora Health. He is also an adjunct lecturer at Northwestern University's Kellogg School of Management and serves on the clinical faculty of the Yale School of Medicine. Additionally, Dr. Khan is a director on the American Board of Internal Medicine. Also a trusted advisor on Pear’s Health Industry Council.Before Aetna, Dr. Khan played a key role in Oak Street Health’s rapid expansion, scaling it from 21 to 200+ clinics, culminating in its acquisition by CVS Health. Prior to that, he was instrumental in CareMore Health’s growth and innovation in care delivery for vulnerable populations.He holds an MD-MPP from Virginia Commonwealth University and Harvard Kennedy School, completed his residency at Yale, and has taught at institutions like Northwestern Kellogg and Yale School of Medicine.As a leader in value-based care, he has firsthand experience in building, scaling, and optimizing healthcare startups—making his insights invaluable for founders, investors, and industry leaders navigating the complex world of healthcare innovation.

Sam Holliday, CEO and Co-Founder of Oshi Health, is redefining gastrointestinal care through his innovative virtual GI center. He discusses the integration of multidisciplinary teams and evidence-based practices to enhance patient outcomes. Sam highlights the importance of holistic health approaches, addressing the gut-brain connection, and mental health in treatment. He also shares insights on tackling workforce shortages in gastroenterology and the strategic funding that fueled Oshi's growth, all while ensuring accessible, high-quality care for patients.

This series aims to demystify Medicaid, starting with insights from federal and state agencies, FQHCs, and managed care organizations, before exploring successful founders' strategies. Readour primers on the key players and innovations here, and stay tuned for upcoming posts featuring interviews with key opinion leaders, purchasers, and startup founders.Cityblock Health is a value-based healthcare provider focused on the complex clinical, behavioral health, and social needs of dually eligible and Medicaid recipients. Cityblock offers the only fully integrated and multi-modal solution that directly delivers clinical care to one of the most at-risk and hardest-to-reach populations. Powered by advanced technology that provides its care team with a data-driven understanding of member needs and risks, Cityblock has demonstrated industry-leading engagement, member retention, meaningful reductions in avoidable hospital readmissions, and reduced total cost of care.Founded in 2017, spun off by Sidewalk Labs, and based in New York, Cityblock has raised nearly $900M to date from investors such as SoftBank, Tiger Global, Maverick Ventures, General Catalyst, Thrive Capital and 8VC, among others. It is now valued at $5.7B. Cityblock currently serves more than 100,000 members, and partners with four national Medicaid health plans and several health systems in 15 cities across seven states.Mike's career has spanned both legal and healthcare leadership roles, starting as a commercial litigator before joining UnitedHealth Group as National Vice President of Medicaid Policy and Product. He went on to serve as CEO of UnitedHealthcare Community Plan of Ohio, then as Chief Transformation Officer and President of Government Programs for Optum BH Solutions, and later as Chief Growth Officer and SVP of Growth and Product at UnitedHealth Community and State. In 2024, he joined Cityblock as President to help drive the company's next phase of growth.Mike holds an undergraduate degree from the University of Notre Dame, a JD from Notre Dame Law School, and attended an Executive Education Program at Stanford Graduate School of Business.In this episode, we learn about how health plans evaluate startups, the complexities of improving access for Medicaid and dual-eligible populations, and Cityblock's innovative approach to building trust and engagement.