Building AI that expands what's possible for people - not just what's possible for companies.
"A sense of purpose is just how powerful a motivator."
Natalie Gibralter arrived at Squarespace when it had 70 employees and no product manager. She didn't find the e-commerce opportunity on a roadmap - she found it by noticing what wasn't there. She volunteered to validate it herself, then spent a decade building it into one of the company's core revenue lines, eventually becoming VP of Product for Commerce as the company went public.
Now she's at Microsoft, running an internal "startup" as VP of Product, AI Innovation for Microsoft Experience and Devices. The title changed. The instinct hasn't: identify the gap, prove the hypothesis, build the team.
Before Squarespace, she was at KIND Healthy Snacks when it had around 10 people, building the KIND Movement social mission and running a national program of 14 brand ambassadors at 21. Before that, she watched young Israeli backpackers in South America staying exclusively in insular groups, and decided to do something about it. She raised nearly $100,000, moved to Israel, and founded TrailTalks - a nonprofit focused on breaking down barriers to cross-cultural connection among young Israelis traveling abroad.
The through-line is consistent: she goes where the problem is, figures out how to solve it with limited resources, and builds institutions - teams, platforms, organizations - that outlast the initial spark. Oxford's PPE program (Philosophy, Politics, and Economics) gave her the intellectual toolkit. Everything since has been field work.
Challenges we face as a minority can help develop our strengths.
Studied Philosophy, Politics, and Economics. Became President of the 1427 Committee and the Anglo-American Society. Wrote thesis on the Israeli-Palestinian conflict - a subject that would continue to shape her career for years.
Lived in Argentina after graduation. Met young Israeli backpackers in South America who traveled in closed, insular groups - a small observation that planted the seed for TrailTalks.
Joined when KIND had around 10 people. Revamped the company's social mission and developed the KIND Movement platform. Hired and managed 14 brand ambassadors nationally at age 21. Helped a snack company understand it was in the culture business too.
Founded and led a nonprofit dedicated to breaking barriers to cross-cultural connection among young Israeli backpackers traveling abroad. Raised nearly $100,000 in funding. Moved to Israel to build the organization on the ground. Key lesson carried forward: purpose is the most powerful motivator there is.
Joined when Squarespace had 70 employees. No PM function existed - she built it. Spotted the e-commerce gap herself, volunteered to validate product-market fit, and turned it into a key revenue line. Guided the team through 10x company growth to the public offering. Spent more than a decade building the commerce platform, growing from business development into Director, then VP of Product. Eventually served as Board Member for Melitz, an Israel-based educational organization, in parallel.
Named to Crain's NY's prestigious 40 Under 40 class, recognizing the city's most accomplished young business leaders. Squarespace CEO Anthony Casalena commented on her "adaptability, ingenuity and drive" in the recognition.
Joined Microsoft to lead an internal startup as VP of Product, Azure Communication Services, then transitioned into VP of Product, AI Innovation for Microsoft Experience and Devices. Currently leading "Horizon 2" platform investments focused on helping people and organizations leverage AI in ways that genuinely augment human capability - and expand opportunities broadly across humanity.
"Natalie was part of our commerce initiatives from the beginning. Taking this team from just one engineer, her adaptability, ingenuity and drive have allowed her to thrive in environments both small and large."
She founded a nonprofit before her first tech job. That sequence wasn't accidental - it established the frame through which every subsequent role gets filtered. Does this matter to people? Does it expand something? The KIND Movement, TrailTalks, Squarespace Commerce, Azure Communication Services, Microsoft AI Innovation - all of them pass the same test.
She didn't inherit Squarespace's e-commerce portfolio - she found the gap and offered to prove it was worth solving. It's a pattern: identify what no one else is doing, validate it yourself, then build the team. This is how a product function gets created where none existed, and how a nonprofit gets built from a conversation with backpackers in Buenos Aires.
Leading volunteers in a nonprofit taught her something that most corporate leaders learn too late: authority is borrowed, motivation is earned. She built her leadership style around understanding what moves each person individually - then helping them get more of it. That style scaled from three TrailTalks volunteers to a VP team at Microsoft.
Roughly 30,000 young Israelis travel abroad each year. The pattern Natalie Gibralter noticed in South America was consistent: they moved in tight, insular clusters - interested in local culture and other travelers in theory, but without the skills or structures to actually bridge the divide.
She didn't write a think piece about it. She built an organization. TrailTalks was a nonprofit specifically designed to develop those cross-cultural connection skills - practical tools for a generation she believed could carry less insularity back home, with real implications for how they'd think about neighbors, politics, and peace.
She raised nearly $100,000. She moved to Israel. She ran the program. Then she left - not because it failed, but because she followed the next problem. Squarespace had built a website builder but had no one thinking full-time about what came after the website. She went there next.
The TrailTalks chapter isn't a detour. It's the decoder ring for everything that follows: a relentless belief that connection - across cultures, between customers and businesses, between humans and technology - is the thing worth building.
"A sense of purpose is just how powerful a motivator." The nonprofit chapter gave Natalie Gibralter something most product leaders lack: proof that she could build institutions without a corporate safety net, a runway, or anyone telling her to do it.
Named to the 2022 class of Crain's NY's signature recognition for the city's most accomplished young business leaders - one of the most competitive lists in the New York business community.
There was no product manager at Squarespace when she joined. She created the role, defined the function, and built a team that eventually ran one of the company's core product areas through its public market debut.
Spotted the e-commerce gap unprompted, volunteered to validate it, and built the commerce platform from one engineer into a major revenue line. The business she helped create serves millions of small business owners online.
Founded and directed an internationally-operating nonprofit that raised ~$100K and ran programs for cross-cultural connection among young Israeli backpackers - entirely self-driven, no parent organization.
Selected as a Core Limited Partner in Underscore VC's community network - connecting her with founders building the next generation of impactful technology companies.
Now leading Horizon 2 AI product and platform investments at one of the world's largest technology companies - focused on building AI that expands human opportunity rather than just automating existing processes.
What got you here won't get you there - the skills that make you successful at one stage of growth require reinvention at the next.
Drawing on her decade at Squarespace - from first PM to VP through IPO - this talk dissects what changes as companies scale and why the product playbook that works at 70 people breaks at 700, then again at 7,000.
How mindset shifts - not just process changes - drive real organizational transformation toward outcome-focused, empowered product teams. Grounded in her experience leading large teams through major inflection points.
Profiled for her approach to converting macro-level challenges into specific, actionable solutions - and for building teams that are empowered to do the same without waiting for direction from above.
Discussed her non-traditional path into product management, how she created a PM function that didn't exist, and what she's learned about building teams that can navigate ambiguity and still ship.
She wrote her Oxford undergraduate thesis on the Israeli-Palestinian conflict - years before that subject became the center of her nonprofit work and a recurring thread through her career.
Practices daily meditation and yoga. Maintains strict email-free vacations - a hard boundary most product executives find impossible to keep. She keeps it.
Married to Aaron, a fellow entrepreneur. They spend whatever spare time two young children allow brainstorming startup ideas together - apparently you can take the operator out of the startup but not vice versa.
As an undergraduate, she became President of both the 1427 Committee and the Anglo-American Society at Oxford - an early signal of her interest in bridging perspectives across cultures.
She found Squarespace's e-commerce gap not from a roadmap or a boss's directive - but from using the platform for her own nonprofit's website. She was a user before she was an employee.
Beyond her day job, she is actively exploring ways to engage New York City youth in shared service as a community-building tool - carrying the TrailTalks ethos directly into her current home city.