Built on precision. Guided by fit. Proven by time.
We are more than recruiters. We are headhunters who deliver cultural alignment,
long-term retention, and measurable impact.
Our Five-Year Replacement Program backs every search, because the right hire should make a lasting impact.
We Specialize in Sourcing Talent for Small to Mid-Sized Technology Companies
Technology professionals across North America in our network
Offer acceptance rate in competitive tech markets
Three-year retention rate on leadership hires
Average time from kickoff to first vetted candidates
Focused on Fit. Driven by Results
Calderwood Search helps Cloud, SaaS, AI, and IT Infrastructure companies hire smarter and faster. We combine deep market insight, proven search methodology, and human judgment to deliver talent that aligns with your technical goals, culture, and growth vision.
We think like partners and perform like headhunters
The best talent isn’t always looking, which is why we search the entire market to find the right fit.
At Calderwood Search Partners, we don’t rely on job postings or resume databases. When companies advertise roles or rely on their internal networks, they often hire from the pool of people who are actively seeking new positions, rather than from the broader market of top performers who may be open but not actively applying.
That’s where we come in.
Our role is to look across the entire market to identify and engage the people who are best suited for your role, whether they’re actively exploring new opportunities or simply open to the right one. This approach gives our clients the confidence that they are choosing from the very best talent available in the market — professionals who can take their business forward and make every hiring investment count.
With decades of combined experience in executive search and business leadership, we understand what a poor hire costs in time, trust, and traction. That’s why every candidate we present is proven, pre-qualified, and aligned with your culture and objectives.
To stand behind that work, every placement is backed by our Five-Year Replacement Program, because the right hire should make a lasting difference.
Who We Partner With
We support technology-driven companies across North America with high-impact searches in Technical Sales, Technology, Architecture, and Leadership roles. These are examples of the kinds of organizations that trust us with their most important hires.
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Cloud and Infrastructure Organizations
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SaaS and Software Companies
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AI, Data, and Technology Focused Organizations
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A cloud transformation company hiring a Senior Solutions Architect |
A SaaS platform expanding its national Account Executive team |
An AI company hiring its first Head of Engineering |
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A managed services provider building a Technical Sales team |
A software automation company hiring a Lead Engineer and a QA Manager |
A machine learning platform building a data science team |
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An infrastructure and network services firm recruiting a Director of Engineering |
A workflow solutions company adding a Solutions Architect and Customer Success Leader |
An analytics firm recruiting a CRO |
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A hybrid cloud provider adding a Principal Architect |
A digital product company searching for a VP of Product |
A technology-driven gaming or telecom-related company hiring engineering and leadership roles |
Testimonials
Calderwood Search has proven to be an exceptionally professional and thorough executive search partner
Ryan Smyth
CEO, Carbon60
I have worked closely with Scott on recruitment in two different companies. Many executive recruiters focus only on short-term transactions. Scott’s differentiator is that while he meets and exceeds the current needs of his clients, he also builds long-term value and partnerships. He has consistently delivered strong candidate–company fits and has supported team
Will Stahl
CEO, Offworld Industries
As a video game studio that has been a close partner with Pinnacle Search for some time now, we would categorically recommend them to any future clients considering utilizing them. They have done an exceptional job at diving into an industry unfamiliar to them and becoming experts to help support us, filtering out and finding candidates who are well fit into the roles
Robert Buckley
CEO, Tecklinx
I highly recommend Scott and his team. As a candidate seeking a new position, they provided exceptional guidance and assistance, ultimately leading to my placement as the CEO of Echo Communications. Now on the client side, they continue to deliver outstanding service by partnering with our organization and effectively addressing our recruitment
Douglas Stetson
CEO, FreeFall Aerospace Inc
Calderwood Search has proven to be an exceptionally professional and thorough executive search partner. Scott was able to blend our challenging technical and managerial requirements into a concise and accurate profile, and he then did all the legwork to narrow down to only the most outstanding candidates. They came to us fully vetted and informed