Arena Careers

In 2018, an unprecedented surge of grassroots activism helped flip the House. In 2020, millions of handwritten letters helped drive record voter turnout at the height of a pandemic. And in 2024, people-powered organizing helped narrow the GOP majority in Congress and bolster blue power at the state level. These wins were fueled by everyday people doing something strategic — and shifting power.

At Swing Left and Vote Forward, we don't just ask people to take action — we move them to do the right things, at the right time, with the highest possible impact.

We're looking for a Head of Political to drive our electoral strategy undergirding Swing Left’s role as the smart political friend that “uncomplicates the complex” for donors and volunteers seeking to maximize the impact. As the leader of the political team, this person will lead the organization’s targeting, briefings, and electoral analysis.

ABOUT SWING LEFT

Swing Left’s mission is simple: we make it easy for people to maximize their impact on the most competitive elections to help Democrats win. Since launching in 2017, Swing Left’s one million members have raised more than $140 million for Democratic candidates, civic organizations, and voter mobilization efforts, and engaged more than 50 million voters door-to-door, by phone, and through handwritten letters. What makes us different:

• Swing Left is singularly focused on directing grassroots time and money to help Democrats win close races that will determine the balance of power in our government, from the White House to key state houses.
• We use data and technology to increase volunteer and donor impact by driving the right resources to the right campaigns, at the right time.
• We put people first, delivering a member experience focused on strategic action, not noise—no spam emails, texts, or doomsday messaging.

ABOUT VOTE FORWARD

Vote Forward is a nonpartisan organization that helps grassroots volunteers turn out citizens from underrepresented communities and encourage active participation in our democracy through high-impact voter engagement tactics. Since 2018, more than 250,000 grassroots volunteers have used the Vote Forward platform to send handwritten letters to more than 40 million prospective voters to encourage them to register to vote and turn out for elections. Vote Forward is affiliated with Swing Left.

JOB SUMMARY

As Head of Political, you'll own Swing Left's electoral strategy and targeting, making the high-stakes calls about where we invest grassroots energy and which races to prioritize. You'll set the strategic direction for where and how we invest our grassroots power, and spend significant time building relationships and negotiating partnerships with elected officials, campaigns, and party committees, asserting the critical role of grassroots power for the Democratic Party's success.

This is a role for someone with deep roots in electoral politics and a strong belief in the power of grassroots volunteers. You're non-ideological and mission-driven: strategic about how we build power, when we deploy it, and how we make the case for it. As a department head, you’ll lead our political team and serve alongside other senior leaders, working closely to weave political strategy into our communications, fundraising, and organizing.

While this job will primarily focus on Swing Left's work, the Head of Political will periodically support Vote Forward's outreach to and communication with elected officials.

This is a remote role based in Washington, D.C., with regular in-person meetings and events in the area, plus some travel for team gatherings and other engagements.

This role reports to the Managing Director.

KEY RESPONSIBILITIES

Electoral strategy and targeting (25%)

• Develop and drive processes to evaluate and prioritize target races according to Swing Left’s prioritization criteria (namely, competitiveness in service of winning the balance of power; no issue or ideological threshold; and no Democratic primaries)
• Identify and make recommendations for action on political moments, from the electoral calendar to broader shifts in the political landscape, that create opportunities for fundraising, organizing, or communications
• Develop and lead implementation of electoral activity plans at the national, state, and local levels; write race prioritization memos for internal and external audiences
• Serve as the organization's primary strategic voice on the political map, trends, and the evolving electoral landscape

Relationship management, external engagement, and impact communication (40%)

• Lead day-to-day engagement with campaigns, state parties, party committees, and political stakeholders across presidential, Senate, House, gubernatorial, and state legislative races
• Negotiate and manage partnerships with campaign entities, coordinated efforts, and non-partisan organizations
• Support Vote Forward’s engagement with elected officials
• Serve as a key external representative of Swing Left alongside the Executive Director, engaging with partners, allies, donors, and press; provide on-site support at in-person events
• Assert and defend the value of grassroots political power in conversations with elected officials, party committees, and campaign staff
• Proactively communicate the contributions of Swing Left's members to candidates, state parties, and political stakeholders
• Provide regular electoral insight and updates to the internal team; surface political trends that should inform organizational planning
• Develop and maintain the organization's external partnerships for the long term

Cross-Functional Leadership (35%)

• Serve as a department head and senior leader for the organization. Partner with department heads and executive leadership to ensure political strategy is integrated across every vertical and workstream
• Manage the political team, including two full-time staff (Deputy Political Director and Political Associate) and project-based contract support
• Brief and advise the communications and marketing teams on electoral strategy, political timing, and how to leverage key moments to ensure external messaging reflects the political reality
• Partner with the development team to connect electoral strategy to fundraising narratives; help donors understand the political landscape and why targeted investments matter
• Partner with the civic engagement, data and research, and marketing teams to report Vote Forward’s research findings and results
• Serve as the internal expert on navigating complex or sensitive political dynamics and guide staff across the organization
• Oversee coordination between the political team and cross-functional teams on electoral activities and external partnerships

KEY COMPETENCIES AND REQUIREMENTS

• Strong interest in and alignment with the distinct missions and values of Swing Left and Vote Forward
• At least 8 years of experience in electoral politics — including campaigns, party committees, and/or political organizations — with a strong network across the Democratic ecosystem
• A track record of building coalitions, gaining buy-in, and managing strategic relationships at scale
• A deep commitment to grassroots organizing and excitement about the contributions of volunteers and small-dollar donors; a clear understanding of how people-powered programs drive electoral outcomes
• Excellent written and verbal communication skills with a demonstrated ability to provide outstanding customer service and effectively advocate for desired outcomes
• Ability to diagnose problems quickly, foresee potential issues, and drive toward solutions
• Skilled at managing up and across; ability to effectively advise senior leaders, driving cross-functional alignment
• Demonstrated ability to manage up and across Swing Left’s and Vote Forward’s senior leadership teams, influencing decisions and driving alignment in a startup environment
• Demonstrated success managing and leading staff and building an impact-driven, collaborative team culture
• A commitment to equity and belonging across all identities, and ability to learn and grow in this space
• Located in Washington, D.C. and ability to attend regular in-person meetings and events in the area, plus travel for team gatherings and other engagements.
• Flexibility to work irregular hours during rapid-response or peak moments

LOGISTICS

Hiring Process:

• Applications will be reviewed on a rolling basis
• We are aiming for a start date as soon as possible
• We will communicate about our expected timeline as the process progresses, and all candidates will receive communication from our team regarding their application status

Compensation:

• The pay range is $168,000 - $185,000/year

Benefits for Full-Time Employees:

• Platinum medical, dental and vision insurance: 100% of the premium paid for employees and 50% for dependents
• Health and dependent care FSA accounts
• Employer-paid life and disability insurance
• Retirement plan
• Professional development and remote work stipends
• An unlimited time-off policy + a flexible medical and parental leave policy
• Separate from PTO, our office is closed for approximately 25 business days each year (including federal holidays)

Location and Working Hours:

• This is a full-time, exempt, and remote position based in Washington, D.C. We are a remote team with staff located across the country, with some positions based in D.C. based on essential job functions
• This position is expected to attend regular in-person meetings and events in the D.C. area. Some travel is also required for team gatherings and other role-specific engagements
• We expect employees to be available for virtual meetings and asynchronous collaboration during normal business hours, and sometimes outside of these hours for events or other peak moments

Physical Requirements:

• This remote position requires effective communication with colleagues and partners through phone, video, conference calls, and written channels
• The role involves working on a computer for part or all of the workday, attending in-person meetings and events (most frequently in the Washington, D.C. area), and some overnight travel for team gatherings and role-specific engagements

We are happy to answer any questions you have about our benefits and policies in interviews.

We are an equal-opportunity employer and seek applications from all qualified candidates who are eligible to work in the United States. However, we are not able to sponsor visas at this time. We use E-Verify during onboarding to complete the I-9 Employment Eligibility Verification. We welcome all applicants regardless of age, citizenship, gender identity or expression, national origin, pregnancy status, race, religion, sexual orientation, veteran status, or any other differences.