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Your Search Partner for High Impact Technology and Leadership Talent

We recruit Technical Sales, Engineering, Architecture, Data, and Leadership talent for Cloud, SaaS, AI, and IT Infrastructure companies across North America. Our searches focus on cultural fit, long term performance, and identifying the best talent available in the market.
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Five-Year Replacement Program

If a placed candidate leaves or is terminated within five years, our replacement program ensures your investment is protected:

Year 1

Replacement at NO CHARGE

Immediate protection

Year 2

30% Discount on Original Fee

Shared investment

Year 3

25% Discount on Original Fee

Continued support

Year 4

20% Discount on Original Fee

Extended partnership

Year 5

15% Discount on Original Fee

Long-term trust

Why Clients Choose Us

If a placed candidate leaves or is terminated within five years, our replacement program ensures your investment is protected:
We understand technology-driven environments

We know the challenges technology companies face when scaling teams. Every search aligns with your technical needs, culture, and long-term goals.

We identify the best talent in the market, not just the applicants

We engage high-performing professionals who are fully employed, respected, and often not actively looking. Your shortlist reflects the strongest available talent.

We provide full transparency throughout every search

Two weeks into each engagement, you receive a clear report outlining outreach activity, engagement levels, market insights, and candidate responses. You always know exactly where the search stands.

We stand behind every placement

Our Five-Year Replacement Program reflects our commitment to long-term results, stability, and meaningful impact.

Our Search Process

Discovery and Alignment

We clarify expectations, competencies, success criteria, and cultural fit.

Market Research and Talent Mapping

We define the ideal candidate profile and map high-performing talent across the technology sector.

Outreach and Engagement

We engage both active professionals and high-performing individuals who are not actively seeking new roles.

Evaluation and Short List Development

We assess experience, capability, performance history, and cultural alignment.

Interview Support and Coordination

We manage scheduling, communication, and the feedback loop for alignment at every stage.

Offer Facilitation and Follow Up

We guide the offer process, assist with negotiations, and follow up to ensure long-term success.

Service Models

We partner with growing technology companies across North America, including Cloud, SaaS, AI, Data, and IT Infrastructure organizations. Clients choose us because we identify and engage the strongest talent available in the market and deliver candidates who perform and stay.

Dedicated Search

Our retained search model provides the highest level of precision and partnership.

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TMaaS

Talent Management as a Service provides ongoing monthly recruiting support for multiple roles throughout the year. Includes a cost comparison chart through a modal.

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Talent Alert

Rapid response support for urgent or time-sensitive hiring needs.

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Who We Partner With

We partner with growing technology companies across North America, including Cloud, SaaS, AI, Data, and IT Infrastructure organizations. Clients choose us because we identify and engage the strongest talent available in the market and deliver candidates who perform and stay.

We support high-impact hiring across:

Technical Sales Account Executives Business Development Software Engineering Infrastructure Engineering Principal Engineering Solutions Architecture Enterprise Architecture Data Engineering Analytics AI Positions Product Leadership Operations Leadership Technology Leadership Director Roles VP Roles C-Level Positions Technical Sales Account Executives Business Development Software Engineering Infrastructure Engineering Principal Engineering Solutions Architecture Enterprise Architecture Data Engineering Analytics AI Positions Product Leadership Operations Leadership Technology Leadership Director Roles VP Roles C-Level Positions
Technical Sales Account Executives Business Development Software Engineering Infrastructure Engineering Principal Engineering Solutions Architecture Enterprise Architecture Data Engineering Analytics AI Positions Product Leadership Operations Leadership Technology Leadership Director Roles VP Roles C-Level Positions Technical Sales Account Executives Business Development Software Engineering Infrastructure Engineering Principal Engineering Solutions Architecture Enterprise Architecture Data Engineering Analytics AI Positions Product Leadership Operations Leadership Technology Leadership Director Roles VP Roles C-Level Positions
Technical Sales Account Executives Business Development Software Engineering Infrastructure Engineering Principal Engineering Solutions Architecture Enterprise Architecture Data Engineering Analytics AI Positions Product Leadership Operations Leadership Technology Leadership Director Roles VP Roles C-Level Positions Technical Sales Account Executives Business Development Software Engineering Infrastructure Engineering Principal Engineering Solutions Architecture Enterprise Architecture Data Engineering Analytics AI Positions Product Leadership Operations Leadership Technology Leadership Director Roles VP Roles C-Level Positions

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

Let’s Build What’s Next — Together.

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. 
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Dedicated Search

Dedicated Search is built for senior-level, technical, and hard-to-fill positions where precision, cultural alignment, and long-term results matter. We proactively engage the strongest talent available in the market and deliver a curated shortlist of fully vetted candidates.

How It Works

  • Structured and time-sensitive process
  • Proactive outreach to high-performing, fully employed professionals
  • Rigorous evaluation for capability, cultural fit, and retention potential
  • Ideal for technical, senior management, and executive roles

Why Companies Choose This Model

Five-Year Replacement Program
Access to talent that internal teams and job postings will not uncover
Exclusive focus on your search until completion
Proven success for complex or strategic positions

Pricing

  • Engagement fee starts at five thousand dollars
  • Executive and C-level searches may require an adjusted engagement fee
  • Success fee is twenty-five percent of the hired candidate’s first year base salary

TMaaS — Talent Management as a Service

TMaaS is designed for organizations planning multiple hires throughout the year. Instead of paying a full
search fee for each role, TMaaS provides fixed rate, full-service recruitment support for an entire year.
TMaaS functions as an extension of your internal HR or leadership team.

How It Works

  • Fixed monthly pricing for twelve months
  • Full recruiting support across multiple positions
  • Priority handling of urgent or recurring hiring needs
  • Dedicated recruiter embedded into your workflow
  • Predictable annual hiring budget

Why Companies Choose This Model

Five-Year Replacement Program
More than fifty percent average savings over traditional recruitment fees
Seamless integration with your culture, processes, and leadership team
Ideal for companies experiencing growth or ongoing hiring demand

Pricing

  • Annual fee divided evenly across twelve months
  • Covers all included positions regardless of when they are filled
  • Full cost comparison chart available in a modal