Head of People


Job Title: Head of People
Reports to: Deputy Executive Director
Salary: $110,000 – $120,000/annually, generous benefits package
Location: Madison or Milwaukee, WI (Please note: Employment with the Democratic Party of Wisconsin requires residence or willingness to relocate to the state of Wisconsin.)
Start date: Spring 2024

About The Democratic Party of Wisconsin: WisDems is nationally recognized as one of the country’s highest-performing and most pivotal political organizations. During the 2024 cycle, WisDems will drive massive programs to defend the Democratic majority in the United States Senate by re-electing Senator Tammy Baldwin, to re-elect President Biden for a second term, elect progressive candidates up and down the ballot, and work to build volunteer-led coalitions for the long term. WisDems’ work is grounded in inclusion, respect, and empowerment across race, gender, other dimensions of identity, and the rural/suburban/urban divide. Our work continues year-round, collaborating with partners to build a movement that delivers meaningful change for all Wisconsinites. We seek outstanding applicants who share our values and vision to join the team, help win elections, and build a future where everyone can thrive.

The Opportunity: As the Head of People, you will execute a broad range of HR responsibilities including recruitment and hiring, onboarding, payroll and benefits, compliance, employee relations, performance management, team and manager development, labor relations, and organizational culture and morale. This person will provide visionary leadership, strategic direction, and empathetic management as part of the senior leadership team. This person will work closely with the Executive Director and Deputy Executive Director to infuse equity, inclusion, and belonging, into every aspect of our work at FreeWill. This is a key service-oriented position that requires a high degree of initiative and individual judgment. You’ll have the opportunity to apply your high energy and enthusiasm for the HR profession and make a difference in the lives of employees, while at the same time helping the organization reach our goals in a critical political period.  

Job Responsibilities: 

  • Help to foster a strong culture of growth, development, and feedback.
  • Be a trusted source of advice and information to all team members and organizational leaders
  • Set direction, goals and strategy for the people team and develop a strategic plan.
  • Oversee organization-wide recruitment and hiring to bring in diverse top talent at high velocity, helping WisDems smoothly scale from 100 to 500 while preserving and enhancing our mission, vision, and values.
  • Oversee performance management, including coaching managers through handling performance challenges.
  • Develop consistently high-quality onboarding across the team to set new employees up for success in their roles during periods of rapid growth.
  • Create a manager development program to develop management skills amongst new and existing managers; regularly coach managers through challenges and opportunities.
  • Oversee fair and equitable people policies, compensation structure and process, benefits and offerings.
  • Oversee compliance with state and federal laws, payroll processing and benefits administration.
  • Conduct and resolve investigations in accordance with organization policy and labor union contracts, handling discipline and termination when necessary. 
  • Manage organizational risk, including legal and reputational risks.
  • Manages and resolves complex employee and labor relations issues by conducting effective, thorough, and objective inquiries in consultation with legal advisors. 
  • Create people systems that can scale during periods of fast growth.
  • Develop onboarding and training plans for the organization, including a strategic onboarding and orientation, DEI training, and manager onboarding program.
  • Maintains knowledge of trends, best practices, regulatory changes, and new technologies in human resources, talent management, and employment law; applies this knowledge to communicate changes in policy, practice, and resources to upper management.
  • As a member of the leadership team, provide sound strategic advice to support the ED and other execs about the day-to-day management of the organization.
  • Manage direct reports in all aspects of their work and support their success in the role by conducting relevant coaching conversations, providing and receiving feedback, and creating an inclusive and engaging team culture. More specific tasks could include but are not limited to:
    • Managing and reviewing time off requests
    • Hiring new team members
    • Having constructive conversations with team members on performance
    • Building rapport and trust within your team
    • Leading projects and delegating tasks
  • On year requirements include working outside of normal work hours; including canvassing and other election-preparation as necessary.

Qualifications (Required):

  • Growth Mindset – Able to take and implement feedback.
  • Relentlessly Goal-Oriented – Enjoys working toward and achieving ambitious goals. Keeps calm in stressful situations. Has the capacity and willingness to work long hours during peak season, rolling up their sleeves and getting the work done.
  • Cultural Competency – Able to build authentic relationships across lines of difference, such as race, ethnicity, sexual orientation, class, ability, gender identity, citizenship status, or other identities. Understands how to take an inclusive lens into all aspects of work.
  • Management Skills – Able to manage relationships within your team, bring out the best in your employees, and treat employees equitably across lines of difference; including but not limited to feedback, performance, and engagement.
  • Relevant Work Experience – Has 5+ years of experience managing people or HR teams, including at least 2 years of people management experience.
  • Human Resources Knowledge – Strong knowledge of HR best practices and laws.
  • Sound Judgement – Has experience applying strong judgment and sound advice in complex employment situations.
  • Proven Recruiting Success – Has success in recruiting high performing, diverse talent at high velocity.
  • Training Skills – Able to create training and development systems across individual contributors and managers.
  • Champion of DEI – Has experience leading an organization to become more diverse, equitable, and inclusive through strong DEI programming and coaching.
  • Interpersonal Skills – Has extraordinary emotional intelligence and interpersonal skills – up, down, across, and externally.
  • Human Resources Software Knowledge – Has experience working with HRIS and ATS (specifically Rippling, HR Acuity, JazzHR, and Lattice).
  • Communication Skills – Has superior written and verbal communication skills.
  • Project Management Skills – Is highly organized with strong project management skills.
  • Leadership Qualities – Acts with integrity, professionalism, low ego, and high self-awareness.
  • Experience in Fast-Paced Environments – Comfort moving quickly in a fast-paced environment.

Qualifications (Preferred):

  •  Experience in a political, nonprofit, or startup setting.

Benefits: Great benefits including; excellent health care ($1/month), dental ($1/month), vision ($1/month), life insurance (free), short term and long-term disability (free), TalkSpace virtual therapy, free Calm premium subscription, mileage reimbursement, monthly cell phone stipend, paid vacation days (starting at 10 days), retirement plan with 3% employer match, 3 floating holidays, 9 paid holidays. 

Equity and Inclusion: The Democratic Party of Wisconsin has a vision for a deeply inclusive  and diverse party organization, membership, and electorate. In order to be successful at the  Democratic Party of Wisconsin candidates must have the cultural competence to successfully  work with a diverse array of constituency groups. We especially strongly encourage applicants  with close ties to Black, Indigenous, AAPI, Latinx, Muslim, non-English-speaking, disability, and LGBTQIA+ communities. The Democratic Party of Wisconsin is an Equal Opportunity Employer.

Note on COVID-19: Candidates will be required to verify that they are fully vaccinated against COVID-19 upon commencing employment, except where prohibited by law. Fully vaccinated includes receiving any booster shots recommended by the CDC or other public health authorities within the timeframe recommended. Reasonable accommodations due to disability, medical condition, or bona fide religious belief will be considered on a case-by-case basis for exemptions to this requirement in accordance with applicable law.