Career Opportunity

Director of Talent Acquisition

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Category

Human Resources (HR)

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Location

Chicago, Illinois

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Salary

$165,000 - $185,000

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Job Reference

246526

Job Description

Our client is a private-equity-backed, multi-brand operating platform in the vacation rental and hospitality services space. They partner with founder-led and operator-driven businesses across the U.S. to help them scale while preserving what makes them great locally.


Today, the organization operates across 13+ states, with 55+ brands, 1,700+ employees, and a rapidly expanding leadership footprint. Their growth model combines M&A, organic expansion, and operational excellence, which places an outsized premium on leadership quality, bench strength, and disciplined talent decisions.

They believe talent is a core value-creation lever, not a support function, and are now building their first enterprise-grade Talent Acquisition function to support the next phase of growth.


The Opportunity

We are seeking a Talent Acquisition Director to build and lead the recruiting function from the ground up. This is a foundational role reporting to the VP of HR and working closely with the executive team to deliver the leadership pipeline that fuels growth.

Initial focus will be on the operator pipeline including Brand Presidents and Regional Vice Presidents, as well as leadership development programs and the Owner Relations team. Over time, coverage will expand to Revenue Management, Business Development, and other critical functions as the platform scales.

This is not a role where you inherit a playbook. You will design the strategy, build the infrastructure, and create the processes that define how the organization attracts and secures top talent. If you thrive on building something meaningful in a fast-paced, PE-backed environment, this is your opportunity.


What You'll Do

Build the Function

  • Design and implement the company's talent acquisition strategy, processes, and infrastructure from scratch
  • Establish and manage an ATS, sourcing tools, and recruiting analytics that scale with the business
  • Build and develop a best-in-class team as the function grows, starting as a player-coach who can execute hands-on recruiting while architecting the broader capability
  • Create employer branding and candidate experience standards that reflect the company's culture and values

Own the Operator Pipeline

  • Lead full-cycle recruiting for Brand Presidents, Brand Presidents-in-Training, Regional Vice Presidents, and other senior operational leaders such as Owner Relations
  • Develop robust sourcing strategies to identify and attract top operational talent
  • Build and maintain a proactive talent pipeline, not just reactive requisition fulfillment
  • Partner with hiring managers to define role requirements, calibrate expectations, and improve selection quality

Partner with Leadership

  • Serve as a strategic advisor to executive leadership on talent market dynamics, competitive intelligence, and hiring best practices
  • Lead intake sessions and profile calibration to ensure alignment between business needs and candidate profiles
  • Provide regular reporting on pipeline health, time-to-fill, source effectiveness, and quality of hire
  • Manage external search partner relationships when needed, ensuring accountability and ROI

Scale and Expand

  • Extend recruiting coverage to Revenue Management, Business Development, and other corporate functions as the platform grows
  • Support M&A integration by assessing acquired leadership teams and identifying talent gaps
  • Continuously refine processes based on data, feedback, and evolving business priorities

What You'll Bring

Education & Experience

  • 6+ years of talent acquisition experience, including 3+ years recruiting P&L leaders, general managers, or operational executives
  • Demonstrated experience in distributed services, multi-site operations, or field-based business models (e.g., uniform services, facility services, property management, hospitality, retail operations)
  • Track record of building recruiting functions, processes, or teams, not just inheriting them
  • Experience in a smaller or mid-sized environment where you owned outcomes end-to-end, rather than operating within a large, siloed structure
  • Familiarity with private equity-backed environments and the pace of value creation expectations
  • Bachelor's degree

Functional Skills

  • Expert-level sourcing capabilities across LinkedIn, direct channels, networking, and passive candidate engagement
  • Strong command of ATS platforms, recruiting analytics, and modern sourcing tools
  • Ability to assess leadership competencies, cultural fit, and growth potential in candidates
  • Process design mindset, able to create scalable, repeatable systems that improve over time
  • Comfort with data and metrics to drive decisions and demonstrate recruiting impact

Soft Skills & Attributes

  • Ability to simplify and break down complex, ambiguous problems into clear modules and methodical next steps
  • Builder mentality, energized by creating something new rather than maintaining the status quo
  • Ownership mentality, you don't wait for direction, you drive outcomes
  • Exceptional executive presence and communication skills, able to partner credibly with senior leaders
  • Bias for action balanced with thoughtful judgment, moves quickly without cutting corners
  • Resilience and persistence, recruiting top leaders is hard, and you're energized by the challenge
  • Alignment with core values around servant leadership, ownership, local presence, and excellence

Compensation & Benefits

  • Competitive compensation package commensurate with experience
  • Annual performance bonus tied to recruiting outcomes and company performance
  • Comprehensive benefits package including medical, dental, vision, and 401(k)
  • Remote-flexible work arrangement with travel as needed




Job Responsibilities

Our client is a private-equity-backed, multi-brand operating platform in the vacation rental and hospitality services space. They partner with founder-led and operator-driven businesses across the U.S. to help them scale while preserving what makes them great locally.

Today, the organization operates across 13+ states, with 55+ brands, 1,700+ employees, and a rapidly expanding leadership footprint. Their growth model combines M&A, organic expansion, and operational excellence, which places an outsized premium on leadership quality, bench strength, and disciplined talent decisions.

They believe talent is a core value-creation lever, not a support function, and are now building their first enterprise-grade Talent Acquisition function to support the next phase of growth.

The Opportunity

We are seeking a Talent Acquisition Director to build and lead the recruiting function from the ground up. This is a foundational role reporting to the VP of HR and working closely with the executive team to deliver the leadership pipeline that fuels growth.

Initial focus will be on the operator pipeline including Brand Presidents and Regional Vice Presidents, as well as leadership development programs and the Owner Relations team. Over time, coverage will expand to Revenue Management, Business Development, and other critical functions as the platform scales.

This is not a role where you inherit a playbook. You will design the strategy, build the infrastructure, and create the processes that define how the organization attracts and secures top talent. If you thrive on building something meaningful in a fast-paced, PE-backed environment, this is your opportunity.

What You’ll Do

Build the Function

  • Design and implement the company’s talent acquisition strategy, processes, and infrastructure from scratch
  • Establish and manage an ATS, sourcing tools, and recruiting analytics that scale with the business
  • Build and develop a best-in-class team as the function grows, starting as a player-coach who can execute hands-on recruiting while architecting the broader capability
  • Create employer branding and candidate experience standards that reflect the company’s culture and values

Own the Operator Pipeline

  • Lead full-cycle recruiting for Brand Presidents, Brand Presidents-in-Training, Regional Vice Presidents, and other senior operational leaders such as Owner Relations
  • Develop robust sourcing strategies to identify and attract top operational talent
  • Build and maintain a proactive talent pipeline, not just reactive requisition fulfillment
  • Partner with hiring managers to define role requirements, calibrate expectations, and improve selection quality

Partner with Leadership

  • Serve as a strategic advisor to executive leadership on talent market dynamics, competitive intelligence, and hiring best practices
  • Lead intake sessions and profile calibration to ensure alignment between business needs and candidate profiles
  • Provide regular reporting on pipeline health, time-to-fill, source effectiveness, and quality of hire
  • Manage external search partner relationships when needed, ensuring accountability and ROI

Scale and Expand

  • Extend recruiting coverage to Revenue Management, Business Development, and other corporate functions as the platform grows
  • Support M&A integration by assessing acquired leadership teams and identifying talent gaps
  • Continuously refine processes based on data, feedback, and evolving business priorities

What You’ll Bring

Education & Experience

  • 6+ years of talent acquisition experience, including 3+ years recruiting P&L leaders, general managers, or operational executives
  • Demonstrated experience in distributed services, multi-site operations, or field-based business models (e.g., uniform services, facility services, property management, hospitality, retail operations)
  • Track record of building recruiting functions, processes, or teams, not just inheriting them
  • Experience in a smaller or mid-sized environment where you owned outcomes end-to-end, rather than operating within a large, siloed structure
  • Familiarity with private equity-backed environments and the pace of value creation expectations
  • Bachelor’s degree

Functional Skills

  • Expert-level sourcing capabilities across LinkedIn, direct channels, networking, and passive candidate engagement
  • Strong command of ATS platforms, recruiting analytics, and modern sourcing tools
  • Ability to assess leadership competencies, cultural fit, and growth potential in candidates
  • Process design mindset, able to create scalable, repeatable systems that improve over time
  • Comfort with data and metrics to drive decisions and demonstrate recruiting impact

Soft Skills & Attributes

  • Ability to simplify and break down complex, ambiguous problems into clear modules and methodical next steps
  • Builder mentality, energized by creating something new rather than maintaining the status quo
  • Ownership mentality, you don’t wait for direction, you drive outcomes
  • Exceptional executive presence and communication skills, able to partner credibly with senior leaders
  • Bias for action balanced with thoughtful judgment, moves quickly without cutting corners
  • Resilience and persistence, recruiting top leaders is hard, and you’re energized by the challenge
  • Alignment with core values around servant leadership, ownership, local presence, and excellence

Compensation & Benefits

  • Competitive compensation package commensurate with experience
  • Annual performance bonus tied to recruiting outcomes and company performance
  • Comprehensive benefits package including medical, dental, vision, and 401(k)
  • Remote-flexible work arrangement with travel as needed

Education and Experience

Knowledge and Skill Requirements

Get to know our
Human Resources (HR) Recruiter

Matt Beck

Account Executive

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(847) 429-2547

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