The Recovering Lawyer Who Built a Culture
Emily Mikailli spends her days on a question most companies never fully answer: what does it take to keep good people, and to make them want to do their best work. As CHRO and Chief of Staff to the CEO at Signifyd, the commerce protection platform headquartered in San Jose, she owns the answer for a workforce spread across four countries. It is a role she grew into over nearly a decade, and one she arrived at by walking away from an entirely different career.
Signifyd sits at the center of online commerce, using machine learning to shield retailers from fraud and chargebacks and to guarantee the payments they accept. The company has raised more than $400 million and reached a valuation that put it among the more closely watched names in commerce technology. But Mikailli's work is not the algorithms. It is the roughly 450 people who build and sell them, and the systems that hold that group together as it scales.
Right now that means running People and Culture and serving as the connective tissue between the CEO and the rest of the organization. She oversees internal communications across global offices, quarterly pulse surveys, weekly notes from the CEO, and a rotating program that puts individual employees in front of company leadership. The goal is deceptively simple: keep a fast-growing, geographically scattered company feeling like one place.
There is room for every type of skill and experience. - Emily Mikailli, on breaking into tech
She did not start here. Mikailli earned a law degree and passed the bar in California before concluding that the practice of law would never give her the human connection she wanted. She has described the pivot with a lawyer's dry humor as "quite an expensive realization." The tuition was sunk; the redirection was not. She moved into tech, and she never looked back.
Silicon Valley, by birth
The setting was not accidental. Mikailli was born and raised in Silicon Valley, the daughter of a father who worked in semiconductor manufacturing. She grew up close to the industry that would eventually employ her, then went east to Duke University for her undergraduate degree before California pulled her back for law school. She has stayed in Northern California since.
Her early tech career ran through two names that shaped her. At Google she got her footing. At SurveyMonkey she found a mentor, Becky Cantieri, whom she still credits as the most inspiring influence on her career, and she watched the company more than double in size during her tenure. That experience of scaling, of building people systems while the ground moves underneath you, became the thing she was best at.
Ten years at one address
In an industry where a two-year stint counts as loyalty, Mikailli has led People and Culture at Signifyd since 2016. She joined when the company was still small and has helped carry it through hypergrowth, opening and staffing offices in San Jose, London, Belfast and New York. Over that stretch the workforce grew nearly fivefold and annual recurring revenue climbed more than twenty-five times. She marked her five-year anniversary in 2021 and has since roughly doubled that tenure, rising from Chief People Officer to a mandate that now includes the Chief of Staff role.
The longevity is itself a statement. People leaders tend to preach retention while cycling through jobs every few years. Mikailli has instead bet on staying, and used the long view to build the kind of culture that is hard to assemble in a hurry.
Get your foot in the door and know your value. - Her advice for anyone trying to break into tech
Against the perfect career path
Her thinking on retention runs against the grain. In a 2026 guest column, Mikailli argued that the secret to keeping talent is not building perfect career paths. The polished ladder, the neatly mapped progression from rung to rung, is the wrong tool. People are messier than org charts, and the leaders who hold onto them tend to meet that mess rather than paper over it. It is a view that reflects her whole approach: business-driven but unmistakably human-centric, more interested in what actually keeps people than in what looks tidy on a slide.
That approach shows up in the texture of her days. Mikailli keeps a disciplined rhythm that would exhaust most people: awake around 3:30 to 4 a.m. for coffee and email, a 5 a.m. workout class, then a workday that can run from five to fifteen meetings covering executive sessions, one-on-ones and manager coaching. She aims to leave by 5 p.m. for family time and to be in bed by 10. The discipline is not for its own sake. It is what lets her hold a global role and still guard the edges of her day for her two children.
The other board seat
Outside Signifyd, Mikailli serves as Vice Chair of the Board of Directors at Parisi House on the Hill, a nonprofit that supports mothers and their children affected by addiction. It is not a line she adds for polish. The same instinct that drives her professional work, a belief that people are worth investing in individually, runs through the volunteer work too. Building teams and supporting families in recovery are, for her, versions of the same job.
She is also, by her own cheerful admission, not all business. Mikailli describes herself as a fashion, pop culture and Bravo junkie and a committed Peloton enthusiast, the kind of person who refuses to flatten her personality to be taken seriously in a boardroom. It works. Colleagues get a leader who is candid, high-energy and genuinely curious about the people around her, not a caricature of corporate seriousness.
What comes next
The widening of her title, from people chief to Chief of Staff, hints at the direction. Mikailli's remit is growing beyond HR into the broader operating rhythm of the company, the place where strategy meets execution. For someone who once decided that a courtroom career could not hold her, it is a fitting arc: she keeps moving toward the work that connects people to purpose, and she keeps bringing more of the company along with her.
Her aspiration, stripped of jargon, is consistent. Build people systems where every type of talent can thrive. Keep healthy culture intact as the company grows. And do the same work of care, on a smaller and more personal scale, for the mothers and children she serves at Parisi House. It is not a flashy mission. It is a durable one, which is rather the point.