Director of Product Operations

Joinfreeworld; United States; Remote; USD 70,000 - 110,000; Full time

Job summary

An established nonprofit organization is seeking a passionate Director of Product Operations to enhance product development and operational efficiency. In this fully remote role, you will collaborate closely with the CTO and engineering teams to implement effective frameworks and ensure alignment with the organization’s mission. Your leadership will be crucial in driving projects forward while maintaining clear communication across departments. Join a dedicated team committed to making a real difference in the lives of individuals affected by the justice system, and help shape a culture of honesty and trust. This is a unique opportunity to contribute to meaningful change while advancing your career in a supportive environment.

Benefits

Remote work flexibility

Health & Disability Insurance

Unlimited PTO

Paid Professional Development

Quarterly Wellness Stipend

Generous paid holidays

Paid parental leave

Qualifications

• 5+ years in product operations or technical program management.
• Proven ability to implement Agile or similar methodologies.

Responsibilities

• Design and improve product development systems.
• Plan and drive execution across product teams.

Skills

Product Operations

Agile Methodologies

Technical Program Management

Communication Skills

Project Management

Tools

Dashboards

Workflows

Job description

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!

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.

Job Description

As our first Director of Product Operations, you'll help us build the operational muscle that enables fast, focused, and high-quality product development. You’ll partner closely with the CTO and engineering leads to implement and evolve delivery frameworks (Agile, Shape Up, or custom rituals), manage cross-functional project execution, and own communication channels that keep everyone aligned.

Your job is to create rhythm and rigor—keeping our teams humming with momentum while staying deeply aligned to our mission and standards of excellence. You’ll serve as a force multiplier for the CTO, ensuring strategy and execution are always in sync.

What you’ll do (Job Responsibilities)

• Design and continuously improve our Agile, Shape Up, or hybrid product development systems.
• Plan and drive execution across product teams, managing scope, dependencies, and risks.
• Own the systems that deliver clear, proactive communication to stakeholders about project status.
• Facilitate planning rituals that keep strategy and execution tightly connected.
• Build dashboards, workflows, or tools that create visibility and reduce ambiguity.
• Translate the CTO’s vision and high standards into operational norms that lift the team.
• Collaborate deeply with engineers, designers, and program teams to keep us aligned and shipping.
• Travel ~4 times a year to working retreats and full-team offsites.

What you’ll have (Minimum Qualifications)

Technical

• 5+ years of experience in product operations, technical program management, or product management.
• Proven ability to implement and evolve Agile, Shape Up, or similar product development methodologies.
• Experience coordinating across product, engineering, design, and other departments.
• Strong ability to track, communicate, and drive progress across multiple projects.

Leadership / Process

• Independent operator who thrives on ownership, clarity, and accountability.
• Highly organized, with a bias toward creating scalable systems.
• Clear, consistent communicator in both written and verbal forms.
• Strong judgment and discernment about what matters most in a mission-driven org.
• Empathy for users and teammates—your work is fueled by real-world outcomes.

Bonus Points if… (Preferred Qualifications)

• You've been impacted by the criminal justice system (directly or indirectly).
• You’ve worked in tech-forward nonprofits, criminal justice, or workforce development.
• You’ve managed delivery teams in an early-stage or rapidly-scaling startup.
• You have hands-on experience with engineering workflows and technical tools.
• You’ve helped translate high-level product strategy into tightly run roadmaps.

Application Process:

• Submit an application and cover letter. If your qualifications are a match…
• We have a short introductory call. If we love each other, then…
• You'll have a call with the CTO to walk through your work history, highlighting your proudest triumphs and the biggest mistakes you've made (i.e. the mistakes that made you).
• One hour take-home exercise.
• Three one-hour panel interviews over video, focusing on Execution & Systems Thinking, Communication & Alignment, and Ownership & Strategic Judgment.
• References - we talk to a few of your previous managers to learn more from the folks who knew you best.
• We agree to terms, and get to work!

Compensation and Benefits

This is a full-time position. Compensation is based on experience, but we are targeting the compensation range provided below.

FreeWorld is dedicated to caring for our team. For an up-to-date list of employee benefits, view our 2025 FreeWorld Benefits. A few key benefits are listed below:

• Remote work flexibility.
• Team-centric culture of honesty, vulnerability, & trust!
• Health & Disability Insurance (medical, dental, vision, mental health).
• Employee Development (Quarterly Wellness Stipend, Paid Professional Development, and more).
• Generous time off (Unlimited PTO, 14+ paid holidays, & paid parental leave).