Arena Careers

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

We’re looking for a Head of Technology to lead our engineering and product team through its next phase of growth and transformation. Your mission will be to see and act on opportunities to use technology to help more people have a greater impact in the 2026 election and beyond.

Using technology to create fantastic experiences for volunteers and small-dollar donors is at the heart of everything that we do, whether that means pushing best-in-class political tech platforms to their limits, incubating early-stage startups, or building products in-house.

This is a senior leadership role for someone who is no longer writing code day-to-day – but has the technical depth, strategic mindset, and people management skills to lead a team of talented engineers, product managers and technologists. You’ll be responsible for growing and managing the team; ensuring high-quality execution by your team; and aligning our product road map and technology investments with our organizational priorities.

You’ll work closely with a highly tech-literate Managing Director, translate product and strategic priorities into scalable, maintainable technology choices, and lead the organization through a critical rebuild phase – modernizing and replacing aging infrastructure while building a tech culture rooted in clarity, accountability, and sustainability.

This role also sits on the senior leadership team of Swing Left and plays a key role in organizational strategy, culture, and development. You won’t be leading a service bureau; you’ll be a strategic partner in the organization and use your expertise to help us devise new ways to leverage technology to win elections. This role reports to the Managing Director.

Your duties will include:

• Manage and grow a team of engineers, analysts, and product managers.
• Dream up moonshot ideas that can transform how volunteers and small-dollar donors participate in elections.
• Maintain awareness of developments in the broader tech industry and identify opportunities to adapt emerging technology to solve problems in politics.
• Chart a long-term plan for modernizing our tech stack – identifying which systems to sunset, rebuild, or replace with off-the-shelf tools.
• Drive architectural decisions with a clear-eyed view of technical debt, sustainability, and capacity.
• Lead build-vs-buy evaluations, including vetting early-stage vendors for reliability and fit.
• Ensure the engineering team consistently delivers high-quality, well-scoped work that reflects product priorities.
• Collaborate closely with other departments to turn organizational strategy into actionable roadmaps.
• Evaluate engineering practices and codebase health—setting standards, reviewing architecture decisions, and ensuring systems are maintainable.
• Work with product managers, designers and members of the marketing team to develop and implement visual design standards across public-facing volunteer tools and web assets.
• Serve as the connective tissue between technical and non-technical staff—translating between domains, surfacing risks and tradeoffs, and keeping communication clear and productive.
• Partner with leadership to ensure our technical direction serves the needs of volunteers, staff, and mission impact.

Qualities of the Ideal Candidate

• Experienced People Manager. You've managed high-performing engineering and/or product teams, and you know how to build trust, deliver feedback, and help others grow. You have a track record of hiring, managing, and retaining great talent.
• Technical Expertise. You have significant experience as a senior or staff-level engineer, engineering manager, or technical lead. You can go as deep as needed in code, architecture, or infrastructure conversations.
• Fluent Across Functions. You’re comfortable in conversations about system design, technical tradeoffs, data pipelines, and product priorities—and you know how to spot gaps in logic, execution, or scope.
• Infrastructure Realist. You’ve modernized aging systems before. You know when to refactor vs. rebuild, when to buy vs. build, and how to evaluate the long-term costs of tech debt or vendor lock-in.
• Mission-Driven. You care about the real-world impact of your work. You’ve worked in or alongside nonprofits, political orgs, or civic tech—or you’re deeply motivated to use your skills in service of public good.
• Aligned With Our Mission & Culture.
  • You have a strong interest in and alignment with the distinct missions and values of Swing Left and Vote Forward.
  • You have a strong commitment to improving the experience of Swing Left and Vote Forward volunteers and small-dollar donors, ideally grounded in past experience volunteering for political campaigns and causes.
  • You have a commitment to equity and belonging across all identities, including but not limited to race, gender, sexual orientation, age, and ability; ability to hear, reflect, act on, and learn from feedback related to identity and equity.
  • You have the ability to work independently and collaborate effectively across teams in a virtual workplace.
• AI-aware. You are deeply versed in the evolving AI landscape, and open to making the maximum possible productive use of new tools and capabilities.

Tech Stack

The Head of Technology is primarily a manager and strategist, not an individual contributor. We don’t expect you to be fluent in every tool that we use or to have had recent experience as an individual contributor, but we do expect enough technical depth to supervise:

• Frontend: React / Next.js
• Backend: Node.js / Express / Flask / Docker
• Data: Snowflake, Fivetran/Airbyte, dbt, Dagster, Lightdash
• Infra: Vercel, Firebase, GCP, Airtable
• Misc: Segment, Supabase, early-stage beta toolsTK

Logistics

Hiring Process:

• Applications will be reviewed on a rolling basis.
• The priority deadline to apply is July 7, but applications will be accepted until the posting is closed.
• We plan to begin interviews in July and are aiming for a September start date.
• 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 starting salary for this position is $160,000 - $170,000/year.
• We provide an annual cost of living compensation increase.

Benefits for Full-Time Employees:

• 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, remote work and technology stipends
• An unlimited time-off policy + a flexible medical and parental leave policy
• Our office is closed for approximately 25 business days (including federal holidays) each year

Location and Working Hours:

• This position is a full-time, exempt, and remote position based in the United States. We are an entirely remote team with staff located across the country.
• 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.
• Some travel is expected for this position, including for occasional in-person meetings.

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.