Overview:

The Last Mile, a San Francisco, CA-based non-profit, is the first prison program in the U.S. to provide in-prison software engineering training. Our mission is to provide opportunities for personal and professional growth for justice-involved individuals through education and technology training. By joining The Last Mile, you will be part of a mission-driven team focused on transforming lives and creating opportunities for justice-impacted individuals.

We're looking for a people-first, strategic, and operationally strong Sr. People Manager to lead our People function and elevate the employee experience across the full lifecycle. In this role, you’ll oversee core People programs, drive key initiatives, and serve as a trusted partner across the organization. You’ll own areas such as benefits, compliance, performance management, employee engagement, and culture-building, with a focus on building inclusive, scalable, and high-impact processes that support our team and our growth. This is a high-impact leadership role for someone who thrives in fast-paced environments, is energized by both strategy and execution, and is excited to shape the future of our People function.

This position reports to the Executive Director and is remote-based. The salary range is based on the employee’s geographic location and experience.
Responsibilities:

Culture, Engagement & Employee Experience

• Design and lead employee engagement strategies, surveys, and action planning.
• Act as a trusted advisor to leadership and staff, modeling the organization’s values.
• Manage and resolve employee relations matters with professionalism, discretion, and legal awareness.
• Provide coaching and support to managers and employees on conflict resolution, performance issues, and workplace concerns.
• Conduct thoughtful exit processes and gather insights to improve retention and organizational health.
• Champion initiatives that promote a strong, inclusive workplace culture.

Compliance, Policies & Leave Management

• Maintain up-to-date knowledge of federal, state, and local labor laws, with an emphasis on multi-state compliance (e.g., CA, NY, TX, WA).
• Ensure HR policies and practices are legally compliant and audit-ready, including wage and hour regulations, leave administration, and benefits compliance.
• Oversee employee leave programs (FMLA, ADA, Paid Family Leave, etc.), including policy creation, eligibility tracking, and return-to-work coordination.
• Draft, update, and maintain HR policies, SOPs, and employee handbooks that are accessible, compliant, and clearly communicated.
• Ensure consistent application of policies across departments and states.

Talent Development, Acquisition & Retention

• Develop and manage onboarding, employee development, and internal learning programs.
• Support managers with tools and frameworks for performance management, feedback, and coaching.
• Partner with hiring managers to lead inclusive and effective recruitment strategies.
• Contribute to compensation and salary benchmarking using internal data and market research.
• Strengthen retention through career development planning and recognition programs.

HR Systems, Operations & Metrics

• Lead implementation and continuous improvement of core HR systems.
• Build scalable, compliant workflows and SOPs to support team efficiency and a seamless employee experience.
• Evaluate and optimize People tools and processes to meet evolving organizational needs.
• Track and analyze key HR metrics such as turnover, engagement, time-to-fill, and training participation.
• Leverage data insights to inform decision-making and present trends and recommendations to leadership.

Benefits Strategy & Oversight

• Serve as the strategic lead for benefits design and implementation.
• Oversee annual benefits renewals and lead any required audits, ensuring compliance with ACA, COBRA, HIPAA, and other relevant laws.

• Ensure benefit programs remain compliant across multiple states and aligned with organizational values and budget.
• Stay informed on benefits trends, benchmarks, and legal updates to make strategic recommendations that enhance the employee experience.
• Collaborate with the Sr. People Generalist on day-to-day benefits administration, employee communication, and issue resolution.

Team Leadership & Collaboration

• Manage, mentor, and develop 1-2 HR team members, fostering accountability and collaboration.
• Partner cross-functionally with Finance, IT, and Operations on system integrations, data flows, compliance initiatives, and change management.

Essential Skills & Experience

• 7-10+ years of progressive HR experience, including 3+ years in a senior generalist or leadership role
• Deep knowledge of U.S. labor laws, multi-state compliance, and HR operations
• Proficient in core HR systems and tools like Google Workspace, Slack, and Culture Amp
• Strong interpersonal, communication, coaching, and project management skills
• Strategic and analytical thinker with a high level of discretion and attention to detail

Additional Attributes

• Passion for People Operations and continuous learning
• Experience with PEOs, DEI, and engagement initiatives
• Background in remote and/or multi-state work environments (preferred but not required)

The Last Mile is an equal opportunity employer and values diversity in our organization. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other protected class. Additionally, we are a Fair Chance Employer, meaning we do not discriminate against justice-impacted individuals or perform background checks. We openly encourage justice-impacted individuals to apply for employment.