There are leaders in tech who build products. Then there are leaders who build connection—both between people, and between vision and reality. Esther Crawford is one of the latter. She’s someone who has worked across early-stage startups, large tech companies, and even built a retreat property, all while investing in the ideas and people she believes in.
In this article I’m going to walk you through Esther Crawford’s story—where she came from, what she’s done, how she thinks, what she values, and what you can learn from her path. Whether you’re an aspiring product manager, someone curious about angel investing, or just interested in someone who blends career success with empathy and real life, there’s something here for you.
1. Early Life & Character Building
Though much about Esther Crawford’s private life remains personal, what is clear from her public profiles is her passion for technology, connection, and empathy. She often talks about her early influences—spaces where people come together, communication matters, and meaning is made.
Her early career isn’t documented in great detail in public sources. What is known is that she has a deep interest in how people connect, through technology. She started working in product and design spaces, building features or products that mattered. The specifics of her education remain private, but you can trace her trajectory by examining her early roles, early projects, and what she chose to work on.
One of her early big moments was founding Squad, a startup that focused on shared visual experiences—ways for people to interact by sharing their screens, experiences, or visuals with others remotely. The idea was that connection over distance could feel more real if people could share what they were seeing, what they were doing. That human-centered approach has been a through-line in her career.
2. Founding Squad & Its Acquisition
What was Squad?
Squad was a startup aimed at making screen-sharing social. Instead of just video calling, the idea was to let friends see what their friends were doing on their phone—browsing, watching, scrolling—together. It was meant to combine multiple forms of expression, making remote hangouts richer.
Her role and why it mattered
As one of the founders, Esther Crawford helped define product direction, growth strategy, user experience, and the larger product vision. It wasn’t just about building features; it was about building meaningful experiences. Users didn’t just want tools—they wanted to feel close to people even when physically apart.
Acquisition by Twitter
Squad was acquired by Twitter (later X) in 2021. After the acquisition, Esther joined Twitter to help integrate what Squad had built into the larger platform. That move gave her insight into operating at scale, taking startup ideas and seeing how they fit inside big infrastructures, tight constraints, user safety, policy, global reach, etc.
This period taught her things you often don’t get at smaller companies: coordination across large teams, aligning product vision with company strategy, handling trade-offs at scale, dealing with compliance, privacy, moderation. All that experience helped her sharpen her leadership in product.
3. Role at Meta
After her time at Twitter (post-Squad acquisition), Esther Crawford moved on to Meta. At Meta she works in product leadership, specifically focused on connecting people through private messaging. Communication, privacy, trust, and empathy are large pieces of her work.
Responsibilities & Projects
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Designing product flows that respect user privacy yet enable deeper connection.
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Working with cross-functional teams (designers, engineers, researchers, policy) to ensure that messaging products are safe, reliable, and meaningful.
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Balancing innovation with caution: new features vs. risk. Meta has lots of infrastructure and expectations, which means you can’t just push something out—you must consider global users, local laws, content moderation, misuse, etc.
Impact
Her influence is evident in internal metrics (user engagement, safety, trust), but also in the more qualitative side—how people feel when they use these messaging platforms. Products that let you be vulnerable, let you share, let you feel close when far away—they often owe something to product leaders who care about human connection, not just clicks or growth.
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4. Investing & Angel Activity
Esther Crawford is not just a builder, she’s an investor. She writes pre-seed and seed checks, often modest in size (for angel investing), but strategic.
What she looks for
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Founders: people who are communicative, earnest, focused on solving real problems.
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Product ideas that emphasize connection, empathy, or improved communication.
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Early stage ventures—where risk is large but so is potential, and her own experience can add value.
Examples & Process
She tends to invest smaller amounts (for example ~$25,000 checks as a scout) but she also offers advice, mentorship, network. Her role isn’t just financial. She has said that she values alignment: do I believe in this product? Do I believe in these people?
Through investing, she extends her influence—helping shapes early-stage products, helping founders avoid pitfalls she’s encountered, and pushing forward ideas that might create more connection, or more empathy, or more meaningful tech.
5. Fable Sonoma & Other Ventures
One of the less tech-oriented but very telling parts of Esther’s life is Fable Sonoma.
What is Fable Sonoma
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It’s a 10-acre property about an hour north of San Francisco.
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It serves as a retreat, team offsite space, family-rental, etc. The idea is to create a place for people to get away, relax, connect, reset.
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More than just a business, it reflects her values: nature, rest, connection, being away from screens, being with people.
Why it matters
Tech life can be frenetic. Long hours, many meetings, constant attention. Having a place like Fable Sonoma speaks to balance. It’s not just side business—it’s a reflection of a philosophy: human beings need pause, reflection, nature, time away. It’s also a way to live what she believes: connection, presence, restoration.
6. Public Presence & Influence
Esther also expresses herself publicly in a number of ways. These help show how she thinks, what she values, and why she matters beyond jobs and titles.
Medium & Writing
She writes on Medium about her time in startups, lessons from product, reflections on leadership, mistakes, growth. These writings help people who are earlier than her to learn. Her style tends to be honest, introspective, humane.
Social Media
She is active on Instagram, Twitter (formerly), LinkedIn. Not just posting achievements, but reflecting on what matters: relationships, connection, empathy in tech. Her personal brand is consistent: she cares about building something meaningful, not just building fast.
Recognition & Community
Because of her work, she has a community following. She’s recognized by peers, founders, product managers. People quote her, reach out to her. She’s a mentor, a speaker. That gives her both authority and trust in the field.
7. Philosophy, Values & Contributions
To understand Esther Crawford, you can’t separate what she builds from why she builds.
Empathy & Connection are at the core. She repeatedly expresses that technology isn’t just tools—it’s about bringing people closer, helping them feel understood, helping them feel human even when far apart.
Balance & Rest also come through. Fable Sonoma isn’t just a place for others, but also signals the necessity of rest, reflection. She seems to believe that creativity, leadership, and good product require rest and perspective—not constant hustle.
Integrity & Humility show up. She does not portray herself as perfect. She talks about lessons, failures, trade-offs. She invests in early-stage ventures because she wants to help, not because it’s only about returns.
Experience & Expertise: Her work at small and large companies gives her a breadth of perspective. She knows what it’s like to build something from nothing, to scale something, to operate under constraint, to integrate with global policy. That makes her advice, writing, investing credible.
8. Lessons & Takeaways
What can one learn from Esther Crawford’s journey? Based on her work, public words, and observable choices, here are some lessons:
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Build with purpose: When you try to build products that matter—to help people connect, be understood, feel less alone—you attract users, loyalty, trust. Purpose matters.
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Start small but think big: Early startups let you experiment. Later roles teach you scale, durability, systems. Both are valuable.
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Be willing to evolve: Moving from founding your own startup, to being part of a large company, to investing, to real estate / retreats shows flexibility. That adaptability is powerful.
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Invest in rest and self: Retreat spaces, time off, nature—these aren’t luxuries. They fuel creativity, leadership, burnout prevention.
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Share your journey: Writing, speaking, mentoring—these amplify your influence. They also help others. Transparency builds trust.
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Choose alignment: In work, in investments, in projects—choose what aligns with your values. It’s easier to persist when values, purpose, and work are aligned.
9. Recognition & Net Worth
While exact numbers are rarely public, here’s what is known or reasonable:
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She does invest, likely making some returns through early stage deals.
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She has worked in senior product roles at big companies (Twitter / Meta), which generally pay well.
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Owns property (Fable Sonoma), which adds to her assets.
So her net worth is non-trivial, though she does not seem to spotlight it. Her recognitions are more around influence, community, and product leadership rather than awards. She is seen by many as a thoughtful product leader and someone who blends life and work in a meaningful way.
Conclusion
Esther Crawford shows us that success in tech is not just about shipping features or raising funding. It’s about connection—between people, ideas, values. It’s about building products that matter, investing in people, creating space for rest, and leading with empathy.
If you aspire to work in product, or want to bring more human values into whatever you do, here are key takeaways: define what you care about, stay flexible in how you work, invest time in rest and relationships, and keep sharing what you learn.
Her path isn’t perfect, no path is. But the way she threads together purpose, action, leadership, and humanity gives a model that many of us might want to follow.
FAQ
Who is Esther Crawford?
Esther Crawford is a product leader, former founder (of the company called Squad), angel investor, and retreat property owner. She is known for her work at Meta and Twitter, and for building spaces (both digital and physical) that help people connect with empathy.
What did she do at Squad?
Squad was a startup that focused on shared screen experiences—allowing friends to share their phone screen, browse together, etc. She helped lead product direction, then after acquisition by Twitter, worked on integrating aspects into a larger platform.
What is Fable Sonoma?
Fable Sonoma is a 10-acre retreat property about an hour north of San Francisco. It serves as a place for retreats, team offsites, family rentals—spaces that let people rest, reconnect, and get away from the everyday.
How does she invest?
She writes pre-seed and seed stage checks, often smaller ones (for example around $25,000), acting as a scout or early investor. She looks for alignment with her values, in founders and ideas, especially in areas of connection, empathy, or meaningful tech.
What lessons can someone learn from her career?
Some lessons are: build purpose into your work, be open to different roles and scales, invest in rest, communicate transparently, align work with values, continuously learn from both success and failure.
