In October 2023, Summer Health CEO Ellen DaSilva arrived at a defining juncture for her pediatric telehealth startup. Founded in 2021, Summer Health offered parents rapid access to licensed pediatricians via text message. DaSilva, an experienced telehealth executive, launched the company after struggling to reach dependable after-hours care for her children. As her startup grew, the advent of mainstream generative Artificial Intelligence (AI) prompted Summer Health's leadership to consider how they might incorporate the technology into the company's platform and capabilities set. Following a partnership with AI company OpenAI, Summer Health's engineering team developed a pilot to create a new AI medical note summarization tool that proved highly useful to pediatricians. As DaSilva looked forward, she considered whether to integrate AI more deeply at Summer Health, even at the expense of her current product roadmap and company priorities.