Description
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
Requirements
• 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
Skills Required
- 5-8 years of full-cycle recruiting experience in a fast-paced, high-growth environment
- Demonstrated success recruiting manager and director-level roles
- Skilled discovery partner and active listener, comfortable handling ambiguity
- Comfort with AI-assisted outreach, matching, and pipeline management
- Hands-on experience with Gem, Juicebox, SeekOut, HireEZ, or Findem
- Systems builder who creates recruiting processes, tools, and hiring manager training
- Experience leading or coordinating contract, offshore, or junior recruiting resources
- Experience with psychometric and aptitude assessment tools
- Familiarity with Culture Index, Criteria, or similar assessment platforms
- Strong ATS discipline and data hygiene
- Executive presence and ability to challenge and advise hiring managers
- Fast, decisive execution; ability to keep searches moving without sacrificing quality
- Background in gaming, entertainment, or tech
- Agency recruiting experience
- Experience supporting recruiting across multiple business units or a portfolio
What We Do
Are you interested in working for the 5th largest terminal operator in the state of Illinois? If so, check out the opportunities Lucky Lincoln Gaming offers! Founded in 2013, Lucky Lincoln Gaming, LLC is a licensed Video Gaming Terminal Operator in Illinois. We provide exceptional service to our clients and customers. Our expertise and experience have enabled us to become a successful company ranking in the top Terminal Operators in Illinois in terms of average profit per location for operators in excess of 100 locations. As Lucky Lincoln Gaming, LLC continues to grow, we will be building out the infrastructure for several other entities in different industries including, Lucky Bet sport wagering, Midwest Property Management, and the new Cannabis company, Cloud 9 dispensaries and Highland Flour cultivation centers. We’re disrupting the industry with innovation! We are pioneers and innovators of our industry. We have swag. We have pride. We own our responsibilities and wake up every morning ready to be better than we were the day before. This is an adventure that has no limits. Why not jump on board? We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We are committed to an inclusive, equitable and accessible workplace. Accommodations are available on request for candidates taking part in all aspects of the selection process.
Why Work With Us
People are the most important ingredient at Lucky Lincoln Gaming. Each team member makes an impact on our business and we share a genuine entrepreneurial spirit and relentless drive to always raise the bar. Together, we nurture a deep sense of community in our organization with a true passion and love for what we do.
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