The Deputy People Operations Director will play a critical role in overseeing and implementing people operations strategy at Scale to Win, managing internal systems, policies, and practices in the day-to-day while ensuring alignment with our organizational goals and values as we scale and evolve.

The Deputy People Operations Director will work together with the Head of People to oversee the administration of people operations, lead talent management, and foster employee engagement throughout the employee lifecycle, from recruiting outstanding talent to co-creating a best-in-class culture that reflects core values around racial equity, diversity, and belonging. Through implementing processes, tools, training, and policies, this position will support the passionate, creative team at Scale to Win to grow and thrive as individuals and together as an organization.

The ideal candidate for this position is a seasoned people operations professional with experience building and scaling progressive organizations and companies. You have a deep understanding and dedication to building values-aligned systems and structures that center the employee experience while building a thriving and successful organization. As the first Deputy People Operations Director at Scale to Win, you will have the latitude to implement innovative solutions and build on foundational systems, and we hope you will bring the skills, expertise, and passion to do so.

Required Skills for this Role

5+ years experience in Human Resources or related fields, including prior experience as a senior People Operations leader
Demonstrated experience creating and implementing people operations strategies, processes, tools, and trainings
Knowledge of relevant laws and regulations and ability to ensure compliance and secure documentation of personnel data
Demonstrated ability to scale an organization quickly, while centering a positive employee experience and building a strong culture
Ability to train managers and guide employees through the entire employee lifecycle from recruitment to offboarding, including onboarding and performance improvement
Commitment to learning and implementing current best practices in the people operations field
Ability to engage diverse individuals around a common goal, demonstrating and applying emotional intelligence, sensitivity, and confidentiality in interpersonal communications
Commitment to Scale to Win’s goals and theory of change, and passion for grassroots organizing and commitment to progressive policy change as well as deep dedication to the mission
Must be creative, strategic, collaborative, and organized, with keen attention to detail
Ability to work independently and to exercise sound judgment and discretion
Comfort working in fast-paced environments and ability to navigate complex and nuanced situations

We Hope You Bring One or More of These Bonus Skills

Experience at start-ups, tech or SaaS companies, and/or Democratic politics
Experience building a People Operations strategy from the ground up
Experience in building staff training, leadership development, and/or mentorship programs
Experience with recruiting, managing recruiters, and/or creating recruitment processes with a focus on diversity, equity, and inclusion

Core Responsibilities

People Operations Management

Build people operations infrastructure and manage day-to-day people operations administration, including total rewards/compensation and benefits, performance management, team engagement, recruitment and onboarding, and learning and development initiatives
Serve as a point of contact for employee complaints, managing the intake, documentation, and resolution process with discretion and professionalism, ensuring compliance with company policies and legal requirements
Manage people operations platforms and HR systems (Gusto and PurelyHR), streamlining wherever possible
Keep Scale to Win’s handbook, policies, leveling guide, and other internal documentation up-to-date, making changes as needed and with the approval of the Head of People
Manage process and logistics for any disciplinary actions that arise, including compiling documentation, ensuring compliance, leading investigations, and coordinating with outside consultants and lawyers
Ensure compliance with all state and federal regulations and develop and implement policies, processes, training, and initiatives to support human resource compliance
Maintain people systems and ensure data integrity in all processes and applications
Develop, audit, and enhance our HR practices, keeping up to date on norms and best practices in people operations and human resources

Organizational Culture Building

Foster positive employee experience and support retention through opportunities to connect, learn, and act, resulting in increased trust and organizational impact.
Support the development of Scale to Win’s DEIJ skills and practices. Build upon existing initiatives, develop and implement racial justice, equity, diversity and inclusion efforts, integrating practices into recruitment, hiring, team building, culture setting, and professional development/advancement, while centering equity in all programs and operations.
Provide guidance around best practice and current trends in supporting productivity, recognition, engagement, and team-building initiatives and practices.

Employee Lifecycle & Performance Management

Manage recruitment and hiring processes, including position definition, market research, outreach and posting, interviewing, and reference checking of qualified job applicants, collaborating with departmental managers to understand the skills and capacities required for hiring needs
Conduct orientation and onboarding for all new hires, including drafting offer letters, collecting new employee documentation (e.g., I-9s), conducting onboarding to Gusto and PurelyHR systems, administrating confidentiality agreements, and leading onboarding calls
Manage logistics and process to offboard staff leaving Scale to Win
Drive and support the evolution of Scale to Win’s performance management and two-way feedback processes
Support people managers to conduct performance reviews and implement Scale to Win’s leveling guide, keeping the guide up-to-date and proposing revisions as needed
Prioritize occupational health and safety and accessibility for team members, providing training and regular support for employees
Develop policies and tools to support performance improvement processes

A typical day

A typical day for the Deputy People Operations Director will involve a variety of projects and tasks, from managing the strategic implementation of systems to completing administrative tasks. You might spend your day overseeing training and development initiatives, meeting with people managers to support the implementation of performance reviews, or updating policies for compliance.

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Deputy People Operations Director