Arena Careers

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 upcoming election cycle, WisDems will drive massive programs to hold Republicans accountable, 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: Big things are happening in Wisconsin, and we’re strengthening our leadership team to help guide what’s next. We’re looking for a strategic, hands-on leader to join us and own our operations functions covering Financial Planning and Analysis, Accounting, People Operations, Legal/Compliance & Risk Management, Administration / Logistics, IT/Infrastructure, and Security while reporting to the Executive Director as a member of the Leadership Team. This role blends high-level strategy with deep operational execution, acting as a connector between the financial health of the Democratic Party of Wisconsin and the underlying systems that drive it.

The Team: You will lead a cross-functional team of seven (7) experienced operators, with an average of 4 years of tenure at WisDems. The Deputy Operations Director oversees Legal/Compliance, Budgeting, and Accounting, with additional Assistants, Managers, and Directors on the team.

You’re our person if:

• You’re an exceptional leader who thrives across boundaries. You apply a combination of consent-building leadership, fiscal discipline and operational excellence while effortlessly shifting between finance, people, compliance, and other domains–understanding the nuances of each world without getting lost in translation.
• You lead with confidence and humility. You can guide cross-functional teams without having to master every domain, honoring others’ expertise while providing clear direction.
• You put people at the center. You understand that behind every policy and financial decision are real people–both team members and partners–and you work to ensure they are all valued.
• You simplify complexity. Whether tackling compliance issues, legal considerations, or financial forecasting, you provide clear, decisive recommendations without getting lost in the details.
• You’re both practical and forward-thinking. You manage tradeoffs effectively and have a sense for when to add process and when to remove friction to support growth.
• You don’t just support great work–you do great work. You don’t hesitate to jump into the details, from compliance nitty-gritty to contract deep dives, and everything in between.
• You align with our core principles. Operations at WisDems isn’t just about keeping things running–it’s about building a durable and sustainable organization, where people can do some of the best work of their lives, and protect it at all costs. Really, these principles come first:
• • Accountability & Solution-Oriented: You take full ownership of your actions and commitments, holding yourself and others to a high standard and seeing objectives through to completion. When challenges arise, you approach them with a problem-solving mindset, focusing on solutions rather than pointing fingers, while recognizing that balance and sustainability are essential for long-term success.
  • Collaboration & Teamwork: You succeed by working as a team, stepping up to support teammates, and sharing knowledge freely. You actively break down silos by connecting across teams, inviting different perspectives, and staying open to new ideas. You engage in constructive debate and, once a decision is made, fully commit to the team's success.
  • Growth & Adaptability: You are dedicated to continuous improvement for yourself and your team. You proactively seek, offer, and act on feedback with openness. You anticipate potential obstacles, take proactive steps to address them, and learn from both successes and failures.
  • Respect & Inclusion: You build strong, authentic relationships by treating everyone with kindness, dignity, and trust. You are skilled at working across lines of difference, value the expertise of all colleagues, and approach interactions assuming positive intent. You have the courage to address difficult topics directly and honestly while showing care for others.
  • Transparent Communication: You communicate openly and honestly to build trust and alignment. You are proactive in setting clear expectations, sharing the "why" behind decisions, and providing timely updates. You ensure the right people have the information they need and are comfortable asking for help when you need it.

What You’ll Do at WisDems:

• Act as the leader and facilitator of the “how” for the entire Party through your leadership and direct management of the Operations teams working in close collaboration to support all of the programmatic Departments at WisDems.
• Directly oversee logistics, accounting, compliance, people operations and IT for the DPW and Coordinated Campaign while providing day-to-day leadership to make key operational decisions and facilitate communication between the operations department and the programmatic departments.
• Collaborate with the Executive Director and other members of the senior leadership team to establish policies, operational strategy, and comprehensive budgets that promote our organization’s vision and culture.
• Identify strategic opportunities to increase the efficiency and equity of party operations and staff support.
• Balance compliance with flexibility by consistently making people-first operational decisions that respect both regulations and our values.
• Create an environment where people can do their best work, feel valued for their contributions, and have clear opportunities to develop their skills and advance their careers.
• Partner with the Deputy Operations Director to oversee all day-to-day matters on behalf of the DPW’s Treasurer, including managing relationships with County Party officials, campaign finance filings, and oversight of Party finances and compliance.
• Oversee all physical and technical security operations, ensuring the party’s statewide infrastructure is robust, scalable, and secure.
• Ensure best practice fiscal management, providing oversight of financial systems, controls, and policies to ensure alignment with U.S. GAAP and campaign finance regulations.
• Sponsor all audit activities for the DPW, ensuring the DPW maintains compliance with all governmental and regulatory obligations, as well as operational excellence and compliance across the organization. Examples include: Employment/Taxation Audits, Post-Presidential Financial Audits, 401(k) Fiduciary, and others as required.
• Serve as the primary point of contact for legal matters, and coordinate with DPW’s legal counsel to ensure compliance with all applicable laws and regulations, particularly with issues of campaign finance and contract negotiations.
• In coordination with the Executive Director manage key external relationships with Admin Committee members and key stakeholders in compliance and financial matters.
• Provide stewardship and management to the Party’s 401(k) retirement plan, working with People Operations to ensure our approach to financial wellness is consistent with our core values.
• Provide strategic and operational support for the financial and compliance intersections of the DPW’s People Operation, such as Payroll, Tax, Benefits and Compensation.
• Requirements include working outside of normal work hours; including canvassing and other election-preparation as necessary.

Hard Requirements:

• 5+ years of leadership experience in Operations or related areas.
• Direct experience leading different functional areas simultaneously (think “Finance and People Ops” or “Compliance and Legal”).
• Obtain HRCI Certificate in HR Fundamentals (or equivalent) within 6 months of employment, sponsored by WisDems.

Preferred Qualifications:

• 5+ years of mission-driven operations experience, preferably in a non-profit or NGO.
• 3+ cycles of electoral campaign or political operations experiences.
• Direct experience managing HR, payroll, hiring.
• Knowledge of the operational needs for GOTV.
• Working knowledge of campaign finance reporting software; experience with NGP, ActBlue, accounting software.
• Working knowledge of Google office suite.

How to Apply

Apply by Sunday, September 19, 2025 at 11:59pm CT.

What to include in your application:

A resume

• Want to make sure we don't miss anything important? If possible, please highlight or point out on your resume where your experience aligns with our hard requirements and preferred qualifications (listed above).

A cover letter, including:

• On page 1: Please introduce yourself and explain why you’re a great fit. This isn’t your typical cover letter—skip the fluff and formalities, and just help us get to know you.
• Starting on page 2: Please answer each of these questions in 2-3 paragraphs or less.
• • What excites you most about this role, and why?
  • If you had to pick the top qualities that separate good executives from great ones, what would they be, and why?
  • Imagine you’re our Operations Director. You’ve just come back from the annual budgeting summit, where budget and hiring decisions for 2026 were finalized. Before the meetup, Avery—a respected senior leader—made a compelling case for hiring a project manager to support her team. The executive team rigorously discussed her proposal, but ultimately couldn’t approve the hire. Now it’s your job to share the decision with Avery. What would you say to her? Craft your response as if you’re writing to her directly. (Feel free to make assumptions about this scenario to guide your response.)

Tips

Please be yourself! ChatGPT can sit this one out.

If you meet our hard requirements and follow the application instructions, we promise a real human will review your materials.

You’ll only be able to apply once, so make sure your answers are final before you click submit.

If we can help with an accessibility need, email us at [email protected] and indicate in the subject line that you’re applying for the Operations Director role. (We can only respond to messages related to accommodations.)

Here’s an outline of what the hiring process will look like:

Stage 1: Application

Stage 2: Initial Meeting with Hiring Team

Stage 3: A video call with 2-3 WisDems team members, including someone from our Operations team focused on everyday aspects of the job.

Stage 4: A video call with members of our leadership team, focused on culture and leadership style.

Stage 5: Offer; we hope to extend an offer by mid-November (or sooner, if we find the right person for the job).

We look forward to hearing from you!

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 employer match, 4 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.