Job Description
As our Director of Software Engineering, you’ll report to the CTO and grow the team to about 15 software developers reporting directly to you. Your day-to-day role will be extremely tactical. You’ll probably contribute code sometimes, and you’ll certainly be hands-on in every part of the SDLC. While you’ll be accountable for delivering a rapid stream of amazing, barrier-breaking software, you’ll also invest heavily in training and professional development of early-career engineers with lived experience. (A core value of FreeWorld is that we’re made up of the population we serve; we find lived experience invaluable to imagining and building amazing, barrier-breaking software.)
We work in Next.js on MySQL, and will increasingly incorporate genAI as a first-class level of abstraction. You’ll support our migration of a web app to a ReactNative app, leveraging your experience both derisking large transformative projects as well as your experience with mobile development. You’ll do the best work of your career amongst the kindest colleagues who show you the most appreciation and support you’ve ever seen. You’ll feel more tired and more satisfied at the end of your days, and you’ll be moved to tears reading about the impact you’re having on men and women and their families.
What you’ll do (Job Responsibilities)
- Energetic project management with daily dot-connecting, disambiguating, de-risking, white-glove delivering, and public celebrating.
- Agile coaching to help the team get more leverage out of the framework and become more and more autonomous
- Recruit several seasoned engineers who quickly lead complex projects and healthy refactors
- Recruit several rising engineers who flourish under your care, developing skills faster here than they would anywhere else
- Tighten the bolts on operational excellence and quality control
- Travel at least four times a year to full-team and eng-only working retreats
What you’ll have (Minimum Qualifications)
Technical
- Experience writing easy-to-read, well-tested, low-resource Typescript
- Exposure to, experience with, or deep acumen for evolutionary architecture (e.g. loose coupling, modularity, continuous deployment, and robust test automation)
- Track record of good judgement in adopting 3rd party libraries and services
- Scars from a few egregious mistakes, inc having taken production down a time or two
Non-Technical
- Demonstrated track record of inclusive, uncompromising hiring
- Passion for teaching and talent development
- Expert communication and organization skills
- Ego-free servant leadership AND
- Swagger to earn the high expectations you set for yourself and the team
- Pride in craft – good enough is never good enough for you, AND
- Scrappy and entrepreneurial – you know how to think big & fail fast
- Radically non-judgemental
- Experience working remotely
- Incredibly passionate about our mission and believes everyone deserves a legitimate second chance
Bonus Points if… (Preferred Qualifications) ‍‍
- Impacted by the criminal justice system (directly or indirectly)
- Experience working in the fields of criminal justice or trucking
- Experience working in a tech-based startup or nonprofit
- Experience with Next.js, ReactNative, Prisma, and genAI
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 have a 60-90 minute “CV Deep Dive” call with the CTO to walk through your experiences and what you learned from them. If we agree your journey has lead you right to FreeWorld…
- You complete a short (1hr) “take home” exercise that’s less screening than prep for…
- Four 45-minute interviews with peers and engineers to dive deeper into your core skills and leadership style.
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 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)
- 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, & paid parental leave)
- Creating tremendous impact at scale