Our Journey
The UpGroup was originally founded in 2004 and reimagined in 2021 as a boutique, founder-led executive search firm.
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Today, we partner with a select group of technology companies across AI, data, and high-growth sectors, supporting them through some of the most critical moments in their growth.
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Our work spans early-stage startups through scaled companies, including venture-backed, private equity-owned, and public organizations. Across each stage, the focus remains the same. Identifying and placing the leaders who meaningfully shape the trajectory.
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We take on a limited number of searches at a time, allowing us to go deep with each team and operate as a true partner throughout the process.
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With a strong foundation in executive and senior technical hiring, our approach is collaborative, highly targeted, and built around delivering outcomes, not volume.
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At its core, The UpGroup exists to connect exceptional leaders with companies building what is next.
The UpGroup
Building leadership teams across AI, data, and high-growth technology companies
The UpGroup is a boutique, founder-led executive search firm.
We partner with founders and leadership teams on the hires that matter most. Executive and senior technical roles that shape trajectory, not just fill seats.
Our approach is collaborative, highly targeted, and built around delivering the right outcome, not volume.
We take on a limited number of searches so we can go deep with each team and get it right.
Services
How We Work
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We partner with founders and leadership teams on high-conviction executive and senior technical searches.
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Most of our work happens at inflection points. When the next hire carries real weight and will shape what the company becomes.
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We take on a limited number of searches at a time, allowing us to go deep with each team and run a highly focused, thoughtful process.
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Executive & Senior Technical Search
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We lead retained searches for executive and senior leadership roles, as well as highly specialized technical hires.
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This includes the Director through the C-suite, along with Principal and Staff-level engineers, Distinguished Engineers, and other critical 0-to-1 technical builders.
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Across engineering, product, data, and AI, we focus on identifying individuals who bring both depth and judgment. The kind of talent that not only builds, but helps define what gets built.
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Selective Search Partnerships
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For a small number of clients, we engage in exclusive, success-based searches for senior individual contributors and emerging leaders.
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These are not high-volume engagements. We take them on selectively when there is strong alignment and a clear path to success.
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What Makes This Different
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Fewer searches. Deeper partnership. Higher conviction hires.
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We don’t take on more work than we can do well.
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We don’t send volume.
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We focus on finding the right person and getting it right.
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Cynthia Mason
Founder | Executive Recruiting Partner & Leadership Advisor
About
I’ve spent over 20 years partnering with founders and leadership teams to build companies through the people they hire.
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My work sits at the intersection of executive search and senior technical recruiting, with a focus on the roles that carry real weight. The hires that shape trajectory, not just fill gaps.
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Today, through The UpGroup, I work with a select group of companies across AI, data, and high-growth technology. Most often at moments of inflection, when the next hire will define what comes next.
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I’ve built teams from the earliest days of a company through scale, and I’ve seen firsthand how much the right hire, or the wrong one, can change the outcome.
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This is not a high-volume model. It’s a partnership.
Focus
Executive and senior technical search across:
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C-suite and leadership roles
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Engineering and product leadership
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Principal, Staff, and Distinguished Engineers
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Data, AI, and emerging technology
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How I Work
I take on a limited number of searches so I can go deep with each team.
The work is highly collaborative, grounded in trust, and focused on getting it right.
📩 cynthia@theupgrp.com
📱 206.856.1524
[LinkedIn]
