Why We Built The UpGroup
The UpGroup was founded on a simple observation.
The companies that change industries rarely struggle because they can't find talent. They struggle because the leadership decisions are simply too important to get wrong.
Over the years, I heard the same frustrations from founders and leadership teams again and again. "The candidates looked great on paper, but they weren't right for our company." "The recruiter never really understood what we were trying to build." "We spent months interviewing people who were never going to be the right fit."
The problem usually wasn't a lack of talent. It was a lack of calibration.
That's why I built The UpGroup differently. Every engagement begins with Executive Calibration because the quality of a search is determined long before the first candidate conversation. We work with founders, CEOs, and boards to define the leadership the business actually needs, challenge assumptions, and align on what success really looks like before a search ever begins.
Today, we partner with companies building across AI, Physical AI, robotics, simulation, autonomy, hardware, data infrastructure, enterprise software, and developer platforms. We intentionally work with a limited number of clients at a time so we can become a true extension of the leadership team and help them make one of the most important decisions they'll face.
Executive search is what we do. Helping companies make better leadership decisions is why The UpGroup exists.
The UpGroup
Building leadership teams shaping what’s next across AI, Physical AI, Robotics & High-Growth Technology
The companies that win don't hire faster. They make better leadership decisions.
Every executive hire is a business decision. The best ones change the trajectory of a company.
The best founders don't hire executive recruiters because they need more candidates. They hire them because the stakes are too high to get the decision wrong.
That's why every engagement at The UpGroup begins with Executive Calibration. Before we identify candidates, we help founders, CEOs, boards, and leadership teams define the leadership their business actually needs.
Better leadership decisions build better companies.
We take on a limited number of searches so we can go deep with each team and get it right.
Executive Search for AI and High-Growth Technology
We build executive and senior technical leadership teams across AI, Physical AI, robotics, simulation, autonomy, hardware, data infrastructure, enterprise software, developer platforms, and other high-growth technology companies.
AI has Changed Executive Search
AI has fundamentally changed how we conduct research, synthesize market intelligence, and challenge our own assumptions.
It hasn't replaced judgment. It has raised the bar for it. Technology should automate research.
It should never replace curiosity, executive assessment, pattern recognition, or the trust required to help leadership teams make exceptional decisions.
Amsterdam | Austin | Bay Area | Boston | Los Angeles | New York | Remote | Santa Barbara | Seattle | UK
Services
How We Help
Executive Calibration
Every search begins with Executive Calibration. Before we identify candidates, we help founders, CEOs, and leadership teams define the role, challenge assumptions, and align on what success looks like.
Better questions lead to better searches.
Executive & Senior Technical Search
We lead retained executive and senior technical searches across AI, Physical AI, robotics, simulation, autonomy, hardware, data infrastructure, enterprise software, and developer platforms.
Our work includes Chief Executive Officers, Chief Technology Officers, Chief Product Officers, Chief Engineers, VP Engineering, Executive Product Leaders, Executive GTM Leaders, Founding Engineers, Distinguished Engineers, Principal Engineers, and other executive and senior technical leadership roles.
Leadership Advisory
Sometimes the right answer isn't opening a search.
We help leadership teams think through organizational design, leadership gaps, market realities, and the decisions that come before hiring.
Selective Search Partnerships
For a small number of clients, we conduct exclusive, results-driven searches for senior individual contributors and emerging leaders.
These are not high-volume engagements. We take them on selectively when there is strong alignment and a clear path to success.
Our Approach
We intentionally work with a limited number of companies at a time.
This gives us the capacity to challenge assumptions, bring meaningful market intelligence, and stay deeply involved throughout every search.
Our goal isn't to present more candidates. It's to help clients make better leadership decisions with the right candidates.
Cynthia Mason
Founder | Executive Recruiting Partner & Leadership Advisor
I've spent more than 20 years helping founders, CEOs, and leadership teams make some of the most important decisions their companies will ever face.
Before founding The UpGroup, I served as Global SVP of People across multiple high-growth technology companies, partnering with executive teams through rapid growth, acquisitions, global expansion, and organizational change. That experience fundamentally shapes how I approach every search. I understand the business decisions behind the hire, not just the hiring process.
Today, I partner with a small number of companies building across AI, Physical AI, robotics, simulation, autonomy, hardware, data infrastructure, enterprise software, and developer platforms. My work focuses on executive and senior technical leadership, helping founders define the leadership they need and then finding the people who can help build what's next.
AI has changed executive search. It has made research faster, market intelligence deeper, and challenged all of us to think more critically. It hasn't replaced judgment. It has raised the bar for it.
Technology should automate research. It should never replace curiosity, executive assessment, pattern recognition, or the trust required to help leadership teams make exceptional decisions.
Areas of Focus
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Chief Executive Officers
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Chief Technology Officers
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Chief Product Officers
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Chief Engineers
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VP Engineering
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Executive Product Leaders
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Executive GTM Leaders
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Executive Marketing Leaders/Growth
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Chief Engineers
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Founding Engineers
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Distinguished Engineers
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Principal Engineers
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