People Operations Director

About Us

FreeWorld is a fully remote, tech-enabled, nonprofit organization in the US that helps individuals affected by the justice system obtain high-income careers to end the cycle of recidivism and generational poverty brought on by our country's mass incarceration problem.

Each FreeWorld team member is incredibly passionate about what we do and cares deeply for our program participants (called Free Agents) and our team. All applicants should share our passion for the mission and truly believe that everyone deserves a real second chance!

Serious applicants, please read our FreeWorld Culture FAQ and FreeWorld Core Values before applying.

Our Mission ‍

FreeWorld’s mission is to end generational poverty and recidivism through economic mobility. We do this by:

• Placing returning citizens into high-wage careers at scale.
• Embracing technology and automation to expand our reach.
• Developing a self-sustaining revenue model to accelerate our growth.
• Investing in our team and maintaining a culture of honesty, vulnerability, and trust.
• Creating systemic change by leveraging our deep layers of graduate data in partnership with the Criminal Justice System to become the Gold Standard for re-entry.

About the Role

FreeWorld is at an inflection point as we launch our strategic plan to scale our organization toward our vision to provide every person leaving incarceration with training opportunities toward living wage careers, leading to dramatically reduced recidivism rates.

Today, we are a fully remote organization of 38 full-time employees and contractors. Over the next three years we will scale to over 120 full-time employees, which will require expert People leadership as we navigate major human capital decisions.

Reporting to the CEO, the People Operations Director will play a critical role in helping us preserve a positive and collaborative culture, lead the continued roll out and development of exquisite people processes, be a critical supporter to managers and individuals across the organization in areas of recruiting, training and development, compensation and benefits, and provide strategic guidance and support to senior leadership on all People matters.

In this role you will:

• Lead a people-first organization that supports FreeWorld’s overall mission and vision, making FreeWorld one of the nation’s "Best Companies to Work For"
• Build employee-oriented people practices and initiatives that exemplify and reinforce our high-performance culture - one that values lived experience, redemption, entrepreneurship, collaboration, and strengthening our culture as we scale from 38 to 120+ over the next 3 years
• Oversee and direct core People functions: talent acquisition, talent management, total rewards, employee relations, compliance, organizational design, training and development, employee engagement, and people database systems
• Collaboratively strategize and implement organizational design, systems, processes, and programs that optimize org-wide productivity and employee well-being

This position is 100% remote and reports to the CEO.

You may be right for this role if:

• You’re a business leader that thinks about our organization’s business objectives and builds a people strategy to meet those objectives.
• You’re energized by the idea of joining a rapidly scaling organization that thrives on moving fast and pivoting quickly.
• You excel at building lean, resilient, and robust organizational structures that emphasize team development and individual professional growth

This is not the right role if:

• You dislike change. We tackle growth head-on and full speed ahead. We try something, we fail, we pivot, we plow forward, and then we do it all again.
• You immediately presume that hiring is the solution. Yes, we anticipate growing our team significantly, but our strategy is to focus on automation and technology first and hiring as a last resort.
• Your default talent acquisition mentality is to look for prestigious degrees and work experiences. Yes, these are great “signals” but we have also found that lived experience is just as important to our organization’s success and culture.

Core Responsibilities: Responsibilities include, but are not limited to:

Strategy:

• Partner with FreeWorld’s senior leadership team to build an employee centric and data driven People strategy to align with business goals and growth targets. This will include improvements to our compensation, performance management, and career ladders.
• Build a Talent Acquisition function with a focus on diversity, equity, and lived experience
• Act as a strategic partner to the FreeWorld leadership team and managers by providing advice and counsel on topics like workforce planning, org design, and team dynamics

Talent Acquisition and Management:

• Manage the talent function, talent branding, and candidate experience
• Design and execute initiatives that cultivate a high-performance culture including: a performance review/promotion program, a world-class onboarding experience, and a learning and development program to help employees and FreeWorld achieve meaningful growth
• Implement strategies around onboarding, offboarding, compensation, benefits, talent management, employee engagement, succession planning, and employee relations
• Monitor key People metrics to evaluate the effectiveness of strategies and make data-informed adjustments to optimize productivity

Compliance:

• Develop, audit, and refine employment policies and practices to ensure compliance with all federal, state, and local employment laws and regulations across all People programs

Collaboration:

• Design and implement programs that foster a sense of belonging, engagement and collaboration across a nationally distributed team

Qualifications:

• You have a connection to our mission and values: Our values resonate with you and you hold a strong belief that everyone deserves a second chance.
• You have 10+ years of experience: You’ve built an exquisite people ops function in other startups of 30-500 people before.
• You’re a leader with a growth mindset: You have a demonstrated ability to lead with care and compassion and the business experience to present a strong business case for your proposals.
• You’re a cross-functional team player: You’re a clear, direct communicator who’s comfortable working with colleagues across a variety of teams and backgrounds. You have a cooperative attitude and willingness to learn and assist others.
• You’re tech-forward: You have an excellent understanding of modern people ops / finance tech stacks and look to automate and consolidate systems where possible.
• You’re a problem-solving pro: When you find a problem, you fix it. You have strong analytical skills with a critical, innovative, mindset toward problem-solving and love trying new solutions to old problems.
• You’re a time-management master: You can juggle multiple goals, tasks, and timelines and keep them on track to meet deadlines.
• You do remote work well: You work well autonomously and can navigate the challenges of remote work while staying focused, and connecting with colleagues along the way.
• Preferred, but not required:
• You have been personally impacted by the criminal legal system. We truly value lived experience!
• You have change management experience consolidating people ops / finance systems
• You have worked remotely in a rapidly scaling environment.

Hiring Process

1. Read our FreeWorld Culture FAQ and our FreeWorld Core Values, and if you still think you are a fit…
2. Submit an application and cover letter. If your qualifications are a match…
3. We have a short introductory call. If we love each other, then…
4. You complete a brief task/project related to the role (such as submitting a work sample).
5. You meet 1:1 with a member of management for one hour to discuss your previous experiences and career goals.
6. You meet with four additional team members for a 45-minute (each) focused interview.
7. Last but not least, we talk to a few of the folks you worked with, and if all goes well, we agree on terms.
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Compensation and Benefits

This is a full-time position. Compensation is based on experience, but we are targeting $150,000 - $180,000.

FreeWorld is dedicated to caring for our team. For an up-to-date list of employee benefits, view our 2024 FreeWorld Benefits. A few key benefits are listed below:

• Remote work flexibility
• Team-centric culture of honesty, vulnerability, & trust!
• Awesome Health & Disability Insurance (medical, dental, vision, mental health)
• Financial Health: 401k & High-Yield Savings Account
• Employee Development (Quarterly Wellness Stipend, Paid Professional Development, and more)
• Incredible Work-Life Balance! (Unlimited PTO, 14+ paid holidays)
• 12-16 weeks of paid parental leave
• Creating tremendous impact at scale