Before May Haim Kotlarsky was running an AI marketing company, she was trying to rescue the greeting card from the inconvenience of buying one. The idea was pleasingly small: choose a design on your phone, make it personal, print it, and give someone an actual piece of paper. Technology could do the errands. The sentiment would still be yours.
In 2013, Kotlarsky and her business partner, Ruth Kadosh Tamari, introduced ayolla, an iPhone and iPad app for making printable cards. Their starting point was affection for an object that already worked. They wanted the convenience of a mobile app without surrendering the pleasure of a physical card. A birthday deserved something you could put on a mantelpiece.
Today, Kotlarsky is CEO and General Counsel at The Brief, the AI marketing platform formerly called Creatopy. Between those two businesses sit legal roles in internet radio, streaming television, developer software, and Meta. It is an unusual route into the chief executive’s office: a founder who liked paper, followed by years spent working with the rules governing digital products.
The scale has changed considerably. The question running through the two products is recognizable: which parts of making something can software take care of, and which decisions should belong to the person using it?
A birthday card with a business model
Ayolla began as a company in 2012. Its July 2013 announcement described a straightforward sequence. Customers selected a card, edited the text, and added a photograph from their device, an Instagram album, or its camera. The resulting card could be emailed for printing or sent to a printer through AirPrint. There was no delivery van in the middle of the idea.
Kotlarsky called the app “our bridge between traditional and digital.” The phrase explained the product without requiring a lecture about disruption. Paper supplied the finished object. A phone supplied the tools to make it. The customer supplied the reason for sending it.
The launch economics were equally concrete: the app was free, a card cost 99 cents, and an optional $6.99 starter kit contained ivory cardstock and envelopes. Even the paper had a place in the business plan. The product let people customize an ordinary gesture while skipping a shopping trip.
That early venture gives this career a detail that job titles alone would miss. Kotlarsky had helped create a consumer product before taking the sequence of technology counsel roles that followed. Her professional history contains both the maker’s side of bringing an idea to market and the legal work that accompanies digital businesses.
A digital purchase. A decidedly physical finish.
Radio, television, then the developer’s desk
Her legal career moved through a succession of businesses with different audiences. At Live365, she worked in business and legal affairs. At Rakuten Viki, she held corporate counsel and head of legal roles. Then came GitHub, where her responsibilities included privacy counsel and director of privacy counsel.
These were different kinds of digital company: radio, television, and the platform where developers work together. The progression matters because it places her later AI leadership in a longer career with online products. The Brief follows several chapters in businesses whose services reach people through software.
Her education also crosses institutions and countries. She earned a Bachelor of Laws at the Hebrew University of Jerusalem and a Master of Laws at Georgetown University Law Center, with a specialization in corporations, securities, and financial regulation. Her Georgetown studies included academic distinction and a scholarship for academic excellence.
Those qualifications establish a formal legal foundation. The businesses that followed supplied the changing subject matter. The most visible example of her work at GitHub arrived in the summer of 2020, when a European court decision turned a familiar infrastructure question into an urgent public explanation.
- Live365Business & legal affairs
- Rakuten VikiCorporate counsel / Head of Legal
- GitHubPrivacy counsel / Director
- MetaPrivacy / Monetization AI
- The BriefCEO & General Counsel
When the rules moved under the product
On July 23, 2020, Kotlarsky published an explanation of GitHub’s response to the invalidation of the EU-US Privacy Shield. The ruling concerned a mechanism used for transferring personal data from Europe to the United States. For a service built around international collaboration, the practical question was continuity.
Her piece addressed the decision, the need for an alternative basis for transfers, and GitHub’s existing privacy commitments. Its stated focus was “uninterrupted support for trans-Atlantic developer collaboration.” The language kept the people using the product in view while explaining the legal change behind it.
There is a particular discipline in that kind of writing. A court has issued a decision; customers want to understand what happens to the service they depend on. The explanation has to connect the two. Readers should leave knowing both what changed and what the company is doing about it.
That September, she joined a GDG Singapore discussion titled The Future of Data Transfer as a guest panelist. The conversation dealt with cross-border data and privacy regulation. She also pointed participants toward the Future of Privacy Forum and the International Association of Privacy Professionals for further reading.
Her recommendations were practical places to continue learning after the discussion. The two organizations she named maintain professional conversations about privacy. Giving an audience a next step is a small detail, but it fits the purpose of the appearance: helping people working with technology keep up with a subject that can change around them.
The written explanation and the panel appearance show a public-facing part of her legal work. Privacy was a subject she discussed with developers as well as a responsibility within the company. The audience extended beyond a legal department.
A familiar CEO, a different brief
After GitHub came Meta, where her roles covered privacy, privacy policy, and monetization AI. She joined The Brief as General Counsel in 2025. She now serves as CEO and General Counsel, putting executive responsibility and legal leadership together in one job.
The move to The Brief involved a familiar colleague. Tammy H. Nam reached out to ask whether Kotlarsky wanted to join the team building its AI marketing product. Nam had been her CEO before. In describing the invitation, Kotlarsky joked that with Tammy, “no” is not really an option.
She described being persuaded by the product vision and by meeting the team. Her account named Thibault Imbert, Ovidiu Gavril, Maikao Grare, Griffin Peck, and Deema Tamimi. It also credited her legal colleagues, Alina Ţurcanu and Alexandra Borz. The announcement was full of names rather than a solitary executive posing beside a launch button.
Nam, in turn, described Kotlarsky as “the GC who’s much more than a GC.” That was a colleague’s assessment during the launch, when the business was introducing a product and a new identity. Today, the CEO title makes the breadth of the role explicit.
“The GC who’s much more than a GC.”
Tammy H. Nam, on The Brief’s launch team
Keeping a human hand on the controls
The Brief’s product brings research, creation, launch, and optimization into a connected marketing workflow. Its tools include AI-assisted imagery and copy, design editing, adaptation of creative assets, ad publishing, and performance insights. The company describes a division of labor in which software handles repetitive production while people retain decisions about brand, story, and tone.
For Kotlarsky, that business brings several previous chapters into the same room: consumer product creation, legal leadership, privacy, and monetization AI. Those are established parts of her career. Her current job places them alongside the responsibility of running the company.
Put ayolla beside The Brief and the contrast in scale is striking. One helped someone produce a birthday card at home. The other helps marketing teams produce and manage advertising. Both give users tools for creating something intended for another person to see.
The resemblance offers one reading of the career, with each business addressing a different task. A customer’s personal message mattered in the card app. A team’s choices about its brand matter in the marketing platform. In each case, the product’s usefulness depends on what its user can still decide.
Brand, story, and tone remain decisions for the marketing team.
The colleagues in the frame
A quieter detail comes from Kotlarsky’s thanks to Alexandra Borz. She credited Borz with helping her through onboarding, contributing privacy and security expertise, and doing commercial transaction work. The account gives another person a substantial role in making her own arrival easier.
She also acknowledged the outside advisers involved in the company’s legal work. In thanking Alisa B. Hall, Kotlarsky described partnering with Jackson Hall Strategies as one of her first decisions as The Brief’s General Counsel. She thanked Hall and Olivia Jackson by name. It adds another pair of people to the account of how she began the job.
These acknowledgments give the story some everyday texture. Joining a business involves introductions, onboarding, and decisions about who will help with the work. Kotlarsky’s comments attach names to those steps. The product launch had its public announcement; her thanks offer a smaller view of the professional relationships around it.
Her public activity also includes support for Women in Security and Privacy and recommendations of resources for lawyers moving into in-house roles. These are specific actions, rather than a personality verdict. Alongside the executive titles, they show whom she chooses to acknowledge and help.
The greeting-card venture remains a fitting place to end. It began with two founders wanting to keep a familiar pleasure while making its preparation easier. Years later, Kotlarsky’s job concerns a much larger set of tools and decisions. The modest early product still supplies a memorable introduction: before the AI campaigns, there was ivory cardstock.