Director of Outreach and Engagement
Way to Win
Way to Win is seeking a strategic, relational, and donor relations leader to serve as the Director of Outreach and Engagement. This role is responsible for designing and executing engagement strategies that expand Way to Win’s reach, deepen donor and stakeholder connection, and strengthen long-term community participation across the organization’s vehicles (c3, c4, PAC, and related entities).
Reporting to the Senior Director of Communications, this position bridges donor engagement, communications, and external visibility to ensure that outreach efforts translate into meaningful participation, sustained relationships, and increased investment in our shared mission.
The Director of Outreach and Engagement will work in close collaboration with Donor Advising, Development, Political/Program teams, and Communications to ensure cohesive messaging, strong community touchpoints, and measurable engagement outcomes.
Summary of Responsibilities
1. Outreach Strategy & Audience Growth
Develop and execute a comprehensive donor outreach and engagement strategy aligned with organizational priorities.
Identify and grow key audiences, including prospective donors, partners, and aligned stakeholders.
Build and refine a peer-to-peer outreach model that expands community reach and donor pipelines.
Analyze engagement trends, audience behavior, and participation data to inform strategy.
2. Engagement & Community Experience
Design and own member and stakeholder engagement experiences, including member events, convenings, calls, and community forums.
Partner with Communications to ensure cohesive messaging and compelling storytelling across channels.
Create micro and macro engagement opportunities that connect audiences to strategy and impact.
Support alignment between donor interests and programmatic priorities through coordinated engagement efforts.
3. Recruitment & Retention Support
Own building a sustainable political and donor community that extends beyond election cycles.
Collaborate with Directors of Donor Advising and Development to support recruitment pipelines.
Develop engagement journeys that nurture prospects from introduction to active participation.
Guide renewal and retention strategies through strong storytelling, impact reporting, and meaningful touchpoints.
4. Communications Integration
Work closely with the Senior Director of Communications to align outreach strategy with broader narrative goals.
Ensure donor engagement campaigns are multi-channel, data-informed, and brand-consistent.
Provide input into messaging that strengthens clarity, trust, and external positioning.
Collaborate on donor campaign launches, investment moments, and major engagement pushes.
5. Data & Systems Oversight
Partner with Operations and Fundraising Administration to ensure clean tracking of engagement metrics.
Monitor engagement KPIs (event participation, retention rates, audience growth, conversion rates).
Use CRM and engagement data to inform strategic adjustments.
Way To Win offers a fully remote environment and is proud to offer a robust benefits package:
- Health Care - Comprehensive and robust 100% employee and family paid health care coverage to all employees.
- Retirement Plan - employees are fully vested in the company’s retirement plan 90 days after their start date. Way to Win contributes 6% of the base salary to the employee’s retirement account, regardless of whether the employee contributes or not.
- Life, Short-term Disability, Long-term Disability, and AD&D - Employer-paid Life Insurance, Disability and AD&D.
- Unlimited Paid Time Off.
- Office Closure - 30 days of holiday time, this includes a Spring break, Summer break, Thanksgiving break and an EOY break.
- FSA - Three different tax-deferred FSA accounts (funded by employees) – Health, Commuter (transit/parking — including UberPool), and Dependent Care.
- HRA ($3,000 p/y).
- Family Leave -12 weeks of paid Family Leave for the birth, adoption, or fostering of a child after one full year of employment.
- EAP - Confidential Employee Assistant Program (EAP) to all full-time employees to assist with work and personal challenges.
- Work from Home - $150 monthly mobile phone stipend.
Way to Win is an equal employment opportunity employer and does not discriminate against applicants or employees because of race, color, religion, national origin, sex, age, citizenship status, disability status, genetic information, sexual orientation, or gender identity or expression of an otherwise qualified individual, or membership in any other class protected by applicable law.