Talent Acquisition Manager in Chicago, Illinois at Midwest Real Estate LLC

Highland Holdings is a founder-led, family-owned business operating across gaming, real estate, and technology, generating over $100M in annual revenue. The firm serves as a holding company for multiple operating businesses, including Lucky Lincoln Gaming, Vast, and Highland Real Estate.

The founder is deeply involved across the portfolio, and the people we bring in shape what these businesses can become. We move fast, we build intentionally, and we expect the people who join us to do the same.

About the Role

As Talent Acquisition Manager, you won’t be handed a clean brief and asked to execute. You’ll be expected to walk into ambiguous conversations, ask sharp questions, and come back with a point of view. The leaders you’ll partner with are direct, high-performing, and have little patience for process for its own sake. You’ll need to earn their trust quickly and hold your own in the room.

This role reports directly to the Chief People Officer and operates as a key member of the People function’s leadership: not a back-office support role, but a seat at the table where talent strategy gets built. You’ll own full-cycle recruiting for manager and director-level roles across our portfolio of four companies, lead a team of contract recruiters and an offshore resource, and partner with the CPO on VP+ searches.

You’ll build recruiting infrastructure that creates competence in our hiring managers, not dependency, and you leverage AI to scale that capacity across the portfolio.

What You’ll Own

• Full-cycle recruiting for manager and director-level roles across Highland Holdings, Lucky Lincoln Gaming, Vast, and Highland Real Estate, from intake through offer

• A team of contract recruiters and an offshore recruiting resource, directing their work, ensuring pipelines are healthy, priorities are clear, and quality is consistent across the portfolio

• VP+ search support in partnership with the CPO, including research, candidate identification, outreach coordination, and candidate prep

• Role discovery conversations with leaders who may not have a fully-formed vision, translating ambiguity into a focused search strategy and a candidate slate that helps them see what they’re looking for

• Passive candidate pipelines built and maintained using AI-powered sourcing tools, LinkedIn Recruiter, and direct outreach

• Recruiting infrastructure for hiring managers: intake templates, structured interview guides, scorecards, and training that enables them to run a consistent, high-quality hiring process

• ATS hygiene: accurate requisitions, clean candidate records, and pipeline data you’d be comfortable presenting to leadership at any time

• Recruiting metrics and reporting to the CPO across the portfolio

• Candidate experience from first touch through offer: responsive communication, clear process, and a standard of care that reflects well on Highland Holdings regardless of outcome

Highland Holdings’ employer brand presence across job boards, LinkedIn, and Glassdoor in partnership with the CPO

• 5–8 years of full-cycle recruiting experience in a fast-paced, high-growth environment

• Demonstrated success recruiting manager and director-level roles; you know how to find and engage people who aren’t looking

• A genuine active listener and skilled discovery partner, comfortable sitting with ambiguity and using a candidate slate to sharpen a brief, not just fill one

• Fluent with AI-powered sourcing tools; hands-on experience with platforms such as Gem, Juicebox, SeekOut, HireEZ, or Findem is a strong plus and comfort with AI-assisted outreach, matching, and pipeline management is a must

• A systems builder who creates process because they believe it makes everyone better, and can translate that into tools and training hiring managers will actually use

• Experience leading or coordinating contract, offshore, or junior recruiting resources

• Experience with psychometric and aptitude assessment tools; familiarity with Culture Index, Criteria, or similar platforms is a plus

• Strong ATS discipline; data hygiene is a professional standard, not an afterthought

• Executive presence and the confidence to push back; you’re comfortable challenging a hiring manager’s thinking, reframing a poorly scoped role, and delivering a perspective, not just a slate

• Fast and decisive; you don’t let perfect be the enemy of progress and you know how to keep a search moving without cutting corners on quality

Nice to Have

• Background in gaming, entertainment, or tech

• Agency recruiting experience that sharpened your sourcing instincts and client discovery skills

• Experience supporting recruiting across multiple business units or a portfolio of companies