CEO Pajama Time
Claim This Podcastby Sari Kaganoff
Podcast Overview
<p>CEO Pajama Time takes you inside the after-hour decisions and toughest strategic choices made by founders as they scale. Hosted by Sari Kaganoff, CEO and Founder of Aytza, these conversations are grounded in real-world experience, navigating the key inflection points every CEO faces.</p>
Language
🇺🇲
Publishing Since
12/24/2025
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Recent Episodes
July 23, 2026
Pivoting in public: Building a business that sustains the mission
<p>What do you do when the model you spent years building isn’t working economically, and the only way forward is to drastically change the shape of the business?</p><p>Naomi Allen is the co-founder of Brightline, a pediatric mental health company. She previously held leadership positions at Castlight and Livongo. In this conversation, Naomi talks about leading through profound uncertainty as both a parent and a CEO, especially in the early days of building Brightline during COVID. She shares the "art and science" of making big calls from incomplete data. </p><p>Naomi walks through the hardest chapter at Brightline: after building out a 50 state virtual model to support employers and scaling from nine customers to over 430 in under two years, she realized that the unit economics didn’t work. She got her team into gear, first running experiments and measuring impact week over week and then decided to drastically shift the model to focus on key locations, which led to a rapid four-week wind-down process. She opens up about the deeply personal side of a public pivot, and realizing that even while running a mission driven company you need to be financially viable to continue serving the mission.</p><p><strong>About Naomi Allen</strong></p><p>Naomi Allen is an entrepreneur and health care executive with more than 20 years of experience building high-growth health technology companies. She is the co-founder and executive chair of Brightline, an award-winning therapy and psychiatry practice that provides pediatric, teen, and parental mental health care to families and children up to age 18.</p><p>A mother of three, Naomi co-founded Brightline in 2019 after experiencing firsthand how difficult it can be for families to access timely, high-quality mental health care for children. Since then, Brightline has served hundreds of thousands of families with evidence-based mental health care and support. Today, Brightline serves families through virtual and in-person care across New York, New Jersey, Connecticut, Massachusetts, and Washington.</p><p>In addition to Brightline’s clinical services, the company offers BrightLife Kids, a CalHOPE program delivered in partnership with the California Department of Health Care Services. BrightLife Kids provides free online coaching, resources, and support for California families with children up to age 12.</p><p>Before Brightline, Naomi served as chief growth officer at Livongo, where she led strategic growth initiatives, including market expansions, acquisitions, and IPO preparation. She was a founding team member at Castlight Health, helping guide the company from startup through its public offering, and worked at McKinsey & Company’s Silicon Valley office, where she helped build the firm’s health care technology practice. Naomi earned an MBA from Stanford Graduate School of Business and a bachelor’s degree from the University of North Carolina at Chapel Hill.</p><p>Presented by Aytza</p>
July 9, 2026
Built on trust: Category creation in women’s health
<p>How do you convince investors, patients, and the healthcare system that a new category in women's health needs to exist?</p><p>Joanna Strober is the founder and CEO of Midi Health, the telehealth company providing insurance-covered primary care for women navigating perimenopause, menopause, and beyond. Joanna started Midi in 2021 after her own frustrating search for menopause care, following an earlier career as a venture capitalist and as health tech founder.</p><p>In this conversation, Joanna talks about the early development of Midi, and how the model expanded based on patient need to offer the full scope of what Midi does today. She digs into how she raised venture capital for a category that didn't yet exist, and the economics of building an insurance-covered, clinician-led virtual specialty care model. Joanna also shares how she manages the business today, building a strong, trusted team so she can dive deep ("like a falcon") into new challenges as they emerge, and standing up the New Product Committee, which helps her turn her constant stream of ideas into disciplined, prioritized bets. Joanna also opens up about deliberately becoming a public figure, how she holds her confidence steady against critics, and how intertwined her personal life is with the business.</p><p><strong>About Joanna Strober</strong></p><p><a target="_blank" rel="noopener noreferrer nofollow" href="https://www.linkedin.com/in/joannastrober">Joanna Strober</a> is the CEO and Co-founder of <a target="_blank" rel="noopener noreferrer nofollow" href="https://www.joinmidi.com/">Midi Health</a>, a virtual healthcare platform for women with a focus on perimenopause and menopause. Midi brings expert care, covered by insurance, to women nationwide. Previously, Joanna founded Kurbo, the first digital therapeutic for childhood obesity, which was acquired by Weight Watchers. Joanna also spent 20+ years in direct private equity and venture capital investing in health and consumer companies. She is also the author of the book Getting to 50/50, a primer on how women can succeed and thrive at work and home, and she was named to Forbes' 50 over 50 list of top Innovators, the CNBC Changemaker 2025, and Time 100 Healthcare Leaders.</p><p></p><p>Read up on Joanna & Midi here:</p><p><a target="_blank" rel="noopener noreferrer nofollow" href="https://www.instagram.com/midihealth/?hl=en">Midi Instagram</a></p><p><a target="_blank" rel="noopener noreferrer nofollow" href="https://www.tiktok.com/@midihealth">Midi Health TikTok</a></p><p><a target="_blank" rel="noopener noreferrer nofollow" href="https://www.linkedin.com/in/joannastrober/">Jonna’s Linkedin</a></p><p><a target="_blank" rel="noopener noreferrer nofollow" href="https://www.instagram.com/joannastrober/?hl=en">Joanna’s Instagram</a></p><p></p><p>Presented by Aytza</p>
June 25, 2026
From Basements to Boardrooms: building a new care modality and passing the torch
<p>What do you do when you haven’t yet reached scale, but market conditions have changed and runway is running out?</p><p>Tori Lecomte founded Sesh in 2019 to bring the power of therapist-led group therapy to consumers. Not coming from a healthcare or CEO background, but convinced the modality was dramatically underutilized, she focused on making sure she had market validation, launching a revenue generating in person direct to consumer marketplace, before adding virtual services, expanding to b2b sales, and then ultimately selling the company in 2023.</p><p>In this conversation, Tori talks about the strategic choices and challenges of building Sesh, the marketplace conundrum at the start, the strategic pivot from consumer to employer sales, navigating a crowded mental health market, and being painted as a point solution. Tori shares the challenges she faced raising her next round of funding, how partnership conversations shifted to become acquisitions discussions, and what it felt like to exit before Sesh had hit the scale and impact she had hoped for. She shares what she'd do differently with hindsight and practical tips for founders who find themselves considering their options.</p><p>Tori also gets candid about myth-busting one of the most pervasive startup tropes, the idea that your business is your baby, and how she navigated having her first child at a pivotal time for the company.</p><p>About Tori</p><p>Vittoria (Tori) Lecomte is the founder of Domestic Futures, a project exploring how technology, markets, and institutions are changing the way we form families. Previously, she founded Sesh, a mental health company acquired by Caraway. She began her career as a technology investment banker at Barclays and later joined <a target="_blank" rel="noopener noreferrer nofollow" href="http://Blockchain.com">Blockchain.com</a> as an early employee. She was named to Forbes 30 Under 30 for Social Impact.</p><p>Presented by Aytza</p>
13 total episodes available
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- What is CEO Pajama Time?
<p>CEO Pajama Time takes you inside the after-hour decisions and toughest strategic choices made by founders as they scale. Hosted by Sari Kaganoff, CEO and Founder of Aytza, these conversations are grounded in real-world experience, navigating the key inflection points every CEO faces.</p> - How often does this podcast release new episodes?
This podcast updates daily.
- Where can I listen to this podcast?
This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
Yes, this podcast regularly features guests.
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