Head of People & Culture

Hybrid in the Chicago or Wilmington, DE area, or Remote within the U.S.

Full-Time W2 | $150,000-$170,000 base bonus

Who We Are

Cultivate is a growing portfolio of businesses united by one vision: A World Made Better By Entrepreneurs. Our world today includes Cultivate Advisors, Breakwater Accounting Advisory, Petra Coach, Blackwell HR, and Propel.

We help entrepreneurs build stronger businesses through better leadership, strategy, and execution. We value tactful honesty, transparency, urgency, and taking ownership of meaningful work.

As our portfolio grows, we are bringing our businesses together under a more unified structure. We’re looking for a Director of People & Culture to lead that evolution, building the people strategy, systems, and infrastructure that will support our teams today and as we grow.

The Opportunity

This is an opportunity to do more than manage an established HR function. You’ll help shape how People & Culture operates across multiple businesses, lead integration efforts, and build repeatable processes that can scale with future acquisitions.

You’ll partner directly with the CEO and leadership team, helping leaders navigate people decisions, while also rolling up your sleeves to build the programs, systems, and processes that make the business stronger. You’ll have meaningful ownership, broad visibility, and the opportunity to influence the future of the company.

What You’ll Do

Lead Business Integration and Change

• Lead the people and culture side of integrating businesses into a unified organization in Year One.
• Build a repeatable HR integration playbook for future acquisitions, covering systems, policies, processes, and employee experience.
• Guide leaders and teams through organizational change with clear communication and thoughtful change management.
  
  

Shape People Strategy and Leadership

• Partner with the CEO and leadership team on organizational design, workforce planning, culture, and people priorities.
• Coach leaders through performance management, employee relations, difficult conversations, and leadership development.
• Establish consistent approaches to performance expectations, feedback, and employee development across the portfolio.
  
  

Build Talent and Total Rewards Programs

• Partner with the Director of Recruiting to align talent acquisition with business and workforce needs.
• Develop and improve compensation philosophy, job architecture, and salary structures as the organization grows.
• Oversee benefits strategy, open enrollment, and vendor and carrier relationships.
• Provide direction and oversight for HR administration and employee support, with help from existing team resources.
  
  

Build Scalable HR Operations and Compliance

• Lead the consolidation and optimization of Paylocity, including employee data, historical records, reporting, and standardized workflows.
• Own multi-state employment compliance, including state employer registrations, unemployment insurance accounts and rates, leave requirements, and other obligations that change as our workforce evolves.
• Identify when we need to establish, update, or close state registrations as employees join or leave states.
• Partner with Finance and payroll providers to ensure payroll-related configurations and employer requirements are accurate.
• Create clear HR policies, standard operating procedures, and employee lifecycle processes that support consistency without adding unnecessary complexity.
  
  

What You Bring

• Strategic and hands-on HR leadership: You can advise executives on big-picture decisions and personally build the processes needed to put those decisions into practice.
• M&A integration experience: You know how to bring teams, systems, policies, and cultures together while navigating change.
• Multi-state HR expertise: You understand the compliance requirements of a distributed workforce, including state registrations, unemployment insurance, employment regulations, and leave administration.
• Systems and process thinking: You can improve HR systems, organize employee data, and build repeatable processes. Advanced Paylocity experience is a plus.
• Strong leadership and communication: You build trust, coach leaders, address difficult issues directly, and communicate clearly through change.
• Ownership and adaptability: You are comfortable working in a growing, evolving business where the path is not always established. You identify what needs to happen and move it forward.
  
  

Experience with compensation architecture, international employment arrangements such as an employer of record, or SHRM-SCP/SPHR certification is a plus.

Location and Travel

We prefer someone near Oak Brook, IL, where our Headquarters are located, or in the Wilmington, DE area, where we have two offices, to allow for frequent in-person collaboration opportunities. Remote candidates near a major airport in the Eastern, Central, or Mountain time zones will also be considered.

Travel will typically represent 1% to 15% of your time, depending on business needs.

Why Join Us?

• Build something meaningful: Shape a unified People & Culture function across multiple businesses, with a foundation for future acquisitions.
• Influence business decisions: Work directly with the CEO and leadership team on priorities that affect the entire organization.
• Own your impact: Have the autonomy to improve how we operate rather than simply maintain existing processes.
• Grow with the business: Help build the structure, culture, and employee experience that will support our next stage of growth.
  
  

If you enjoy bringing clarity to complexity, helping leaders become better leaders, and building people infrastructure that makes a growing business stronger, this role offers the scope to make a lasting impact.

Cultivate provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training.