Build the future of employee leave

We’re bringing much needed simplicity to the complex world of employee leave. Today, the process is needlessly complex: going on leave (be it parental, medical, bereavement, or for any other reason) means talking to reps and wading through a mountain of government and insurance claims just to get your time off and income in moments when you're the most stressed and busy. We talked to hundreds of employees and employers who had nightmare stories to tell, so we decided to fix it.

Our mission is to empower every working person to take care of the important things in life when it matters most — removing all of the friction that exists today for both employees and employers — and be the #1 advocate for folks going through the process. It's a really exciting space, and we're moving incredibly fast on both product and user momentum.

Excited about taking the most frustrating processes companies and employees face and making it surprisingly delightful? We'd love to work with you.

What will you do?

You'll lead a team building and scaling our customer-facing leave platform — owning both the people and the technical side of that work. That means setting a high bar for engineering quality, making thoughtful architectural decisions, and actively developing the engineers through coaching, feedback, and clear expectations.

You'll work closely with Product, Design, Operations, and Legal to turn genuinely complex policy and compliance requirements into a leave experience that feels simple and reliable for employees and employers alike. A big part of the job is bringing clarity to hard problems — translating ambiguity into well-scoped work your team can execute with confidence.

As one of our early engineering leaders, you'll also have a real hand in shaping the company itself. How we operate, how we hire, how we scale — these aren't decisions that get handed down from above. We want someone who's energized by those questions and wants to help us get them right.

• ️ You'd be a great fit if you…

• Have led or managed an engineering team working on customer facing product experiences
• Are comfortable navigating ambiguity and bringing clarity to complex or evolving problems
• Have experience leading and shipping large initiatives with high business impact
• Have experience making thoughtful technical tradeoffs, writing and reviewing code, and providing system-level guidance to engineering teams
• Are able to identify, hire, and retain strong engineering talent, including through performance management and coaching
• Care deeply about both the business and your team, and provide candid, constructive feedback while mentoring others and fostering an inclusive environment
• Balance speed of execution while advocating for the right time to slow down to design robust, scalable systems
• Are committed to raising the bar for quality, reliability, and availability
• Debate without ego and enjoy thinking from first principles, questioning assumptions, and continuously improving how things are built
• Prioritize t engineering while building the right product and a strong company culture

Some benefits you can expect as a part of the Cocoon team:

• Competitive salary and equity
• Medical, Dental, and Vision insurance coverage
• Unlimited vacation and sick time
• Professional development budget
• Office setup and wellness stipends
• Company sponsored offsites & more!

Cocoon is aware of fraudulent job offers circulating online from individuals impersonating our company. All legitimate openings are posted on Cocoon - Careers. We will never request payment, gift cards, or sensitive financial information at any stage of our hiring process. Official recruiter communications will only come from maddi@cocoon.com or no-reply@us.greenhouse-mail.io email addresses.