Director of Product Operations

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

Hiring Process

Read our FreeWorld Culture FAQ and our FreeWorld Core Values, and if you still think you are a fit…
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!
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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: