About Our Chicago Office
About Our Chicago Office
Caldwell is an executive search firm in Chicago, Illinois, recruiting board directors, CEOs and senior executives for organizations across the Midwest. Our Chicago office opened in 2019 in the Loop and serves as a hub for the firm’s Financial Services Practice.
Located at 250 South Wacker Drive, the office specializes in recruiting leaders across commercial and consumer banking, digital and fintech, cards and payments, GSEs, mortgage banking and private equity, with a track record of digital and omni-channel build-outs, backed by the reach and resources of a global search firm.
Executive Search Services in Chicago
Our consultants support you across the full leadership lifecycle.
Executive & Board Search
A retained, research-led search for the board directors, CEOs and senior executives who set your organization’s direction. We map the market across the Midwest, assess candidates rigorously, and give you a shortlist you can act on with confidence.
CEO Search & Succession
Appointing or replacing a chief executive is the highest-stakes decision a board makes. We identify and assess CEO candidates and partner with your board on succession, so leadership transitions strengthen the organization.
C-Suite & Functional Leadership
From CFOs and COOs to CHROs and CTOs, we recruit the functional leaders who turn strategy into results across the Midwest.
Financial Services Leadership
As a hub for the firm’s Financial Services Practice, our Chicago team recruits leaders across commercial and consumer banking, digital and fintech, cards and payments, GSEs, mortgage banking and private equity.
Frequently Asked Questions
How do I find an executive search firm in Chicago?
Start by looking for a firm with proven experience at the seniority and in the sector you are hiring for, one that runs a retained, research-led process rather than contingency recruiting, with senior consultants who conduct the search themselves and a genuine local presence. Caldwell’s Chicago office meets all of these. Open since 2019, our team recruits board directors and senior executives across the Midwest. Contact the Chicago team for a confidential conversation about the role you need to fill.
How do executive search firms find candidates?
Through a retained, research-led process. The firm maps the market for a specific role, then identifies and confidentially approaches candidates, including accomplished leaders who are not actively looking, before assessing each against the requirements of the role and presenting a shortlist. Across the Midwest, that disciplined mapping is what reaches leaders who are not on a jobs board.
What is a retained executive search firm?
A retained firm is engaged exclusively for a search and paid in agreed stages, regardless of the eventual hire, unlike contingency recruiters who are paid only when a placement is made. Caldwell has worked on a retained basis for more than 50 years, and the model suits the senior financial services and board-level roles our Chicago team is most often asked to fill, where a thorough and committed search matters most.
