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Chill Labs

Chill Labs is a boutique consultancy helping companies think strategically, solve business problems, and streamline operations utilizing Product Management, Software Engineering principles and AI. Combining a decade of experience running complex, globally distributed software products with expertise in product discovery, user research, and strategy, Chill Labs helps companies build products that users want and do so in a way that supports growth and scale. Dina Levitan, Founder and Principal at Chill Labs, based out of Seattle, WA, brings over 15 years of experience as a product and technical leader ranging from startups to companies like Google.

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Most consultants are urgent care

Hi Reader, A few years ago I saw a functional medicine doctor for the first time. I came in with one complaint, expecting a quick answer and a prescription. Instead she spent the first hour asking about everything else. Sleep, stress, what I ate, what my life looked like ten years ago. She wasn't treating the thing I walked in with. She was trying to figure out what was behind it. I've thought about that visit a lot since. It's close to how I try to work with a business. What I'm noticing...

Hi Reader, I've noticed something about the people doing the most interesting work with AI right now. They're a little weird. Not weird as in difficult. Weird as in they have a rich interior. Strong convictions about how things should work. Unusual hobbies. A distinct way of seeing that doesn't quite match anyone else's. What I'm noticing For a long time, a lot of professional success ran on being reliably competent at ordinary things. Produce the doc, run the process, hit the standard. AI is...

Hi Reader, When my kids were babies, our pediatrician had one rule she kept repeating: let them chew. Pouches and purees are easy. But babies who only get liquid food are slower to develop the muscles that let them bite, and those same muscles matter for learning to talk. They need to work at real food to build the machinery. The same thing is happening with AI. What I'm noticing We are getting very good at consuming ultra-processed information. Summaries of summaries. The takeaways without...

Hi Reader, A few weeks ago I gave a 90-second lightning talk at a conference in Miami. Experiment Live - a meetup for people who work in experimentation and product. Ten speakers, two minutes each, one slide. Mine was titled "AI grows the tree. You prune it." Here's what I meant. The opportunity solution tree Teresa Torres, who writes and teaches about continuous product discovery, has a framework called the opportunity solution tree. The short version: if you're trying to drive an outcome,...

Hi Reader, I was talking with someone who spent two decades leading large engineering teams, hundreds of people at peak. She's figuring out what's next, and she said something I keep hearing: "The thing I got good at was managing people. Delegating, figuring out who does what. But teams keep getting smaller and flatter, and I'm not sure that matters anymore." I told her the opposite is true. What I'm noticing As AI agents start doing real work, drafting, analyzing, handling customer...

Hi Reader, There are parts of parenting I would never automate. The bedtime routine. The walk to school. The moment when they climb into your lap for no reason. Those aren't on the list. But school lunch labels? The dentist reminder that could easily be a recurring calendar event? The forms that come around the same time every year? Those I've automated. Without apology. When I went independent, I told myself I wanted to be more present with my kids. What I learned is that presence has less...

Hi Reader, I've been noticing something in client conversations this past month. The people who are most anxious about AI are the ones with the most knowledge. Senior operators, experienced PMs, accomplished consultants. They know their domain deeply, and they're watching AI get better at knowing it too. The people who seem least anxious aren't focused on knowing more. They're focused on how they show up when it's hard. What got me thinking Joe Hudson - an executive coach who coaches leaders...

Hi Reader, Here's a thought experiment. Or it was, until I ran it on myself a few weeks ago. What if you had to be completely unreachable for three weeks, starting next Monday? It was clarifying in ways I didn't expect. Would your business hold? Most people pause when I ask that. Then they start listing the things that would break. A client expectation that's never been written down. Content that only exists in their head. A monthly deliverable that quietly stops going out. "Automate...

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Hi Reader, Danielle LaFleur ran a 22-person marketing agency. Then she took it apart and rebuilt it as a 4-person AI operations company called EasyAsPie.ai, where everyone does work that matches their actual strengths instead of their job description. The catalyst wasn't strategy. It was sitting down with each person's values and natural gifts and realizing most of them were in the wrong seats. What we covered: The nail salon reframe: a salon owner's real skill isn't owning a salon, it's...

Hi Reader, A few months ago I started working with a woman who spent 25 years in legal marketing, seven of them as a CMO of a $500M+ firm. She knew exactly how to sell other people's expertise. She had no idea how to sell her own. That gap is the most common thing I see in senior people who want to go independent. You've shipped real work for years. You've solved hard problems. But packaging what you know into something a client will pay for? You never had to. The company name did that part...