🚀 Build the future of employee leave

We're tackling the complex world of employee leave. Today, it's fascinating and baffling how complicated the process is: 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, and wondered to ourselves why nobody had solved this yet.

Our mission is to take the work out of leave — 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 insurance, banking, and finance processes out there and making them surprisingly delightful? We'd love to work with you.

💪🏽 What will you do?

As a member of our support team, you'll be assisting and empowering our users as they go through some of their most life-defining moments using Cocoon’s industry-defining software. Cocoon's goal is to support people through some of the hardest and busiest times in their life using technology - how we supercharge that technology is just as important as the product itself. 

You'll be providing expert support to leave-takers and the teams at the Companies that support them. You'll be providing feedback to our Product Team as a critical piece of the product development lifecycle through the data we collect in the support tickets answered. If you love documenting processes, you’ll love working closely with our Product Operations team to bring our Product Solutions team to the next level. 

⚡️ You'd be a great fit if you are:

  • A superb verbal & written communicator: You speak & write clearly, concisely, and with a sense of urgency. You are able to tailor your communication to a variety of situations, and with a wide range of user and customer personas. You can explain complicated topics while maintaining a friendly tone, and can de-escalate uncomfortable situations with grace.
  • A lover of insights: You supercharge our Product Team by sharing feedback & insights.
  • A relationship builder who is comfortable learning technical concepts and legal frameworks: You build relationships by approaching people and problems with thought and care. At the same time, you’re as comfortable breaking down alphabet soup (PFL, CFRA, FMLA) as you are explaining software.
  • A data driven problem-solver: You love working with data and turning insights into actionable improvements. 
  • Dedicated to finding good endings: You seek to understand problems deeply, arrive quickly at well-thought out solutions, and execute on follow-ups.
  • A builder: You’ll build the playbooks and processes for how things work, with an eye for scale.

📈 On the job:

Here's an outline of what your first few months on the team might look like:

  • Month 1:
    • You are able to assist in our support queue by answering Tier 1 tickets that consist of easy and common to solve questions, with self-serve solutions.
    • You are able to utilize templated responses and provide self-serve solutions, and are responsible for identifying and escalating tickets needing a higher tier of support.
    • You successfully pass the Disability Management Employer Coalition's (DMEC) certification to become a Certified Leave Management Specialist (CLMS). 
  • Months 2-3:
    • You are comfortable assisting and escalating tickets into the Tier 2 support queue. Tickets in Tier 2 require more specialization and breadth of product knowledge. These requests frequently involve Product Operations team members for review.
    • You are comfortable providing video and phone support to employers and users.
    • You are able to begin meeting standardized SLAs that are expected of our support team. 

🎁 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
  • 14 weeks of paid parental leave
  • 4 weeks of each paid medical and caregiver leave
  • 4 weeks of flexible, paid compassionate leave
  • Flexible work schedule

The salary for this role is $55,000 to be determined through our interview process.

At Cocoon, we believe that diversity, equity, inclusion, and belonging (DEIB) serve as the foundation for a successful team, product, and community. We’re committed to building a company where everyone can bring their authentic selves to work and be set up for success. Creating a diverse, equitable, and inclusive workforce requires ongoing effort and attention. We are committed to cultivating space for feedback and expanding our understanding of DEIB as our community grows.


We use Covey as part of our hiring and / or promotional process for jobs in NYC and certain features may qualify it as an AEDT. As part of the evaluation process we provide Covey with job requirements and candidate submitted applications. We began using Covey Scout for Inbound on February 1, 2024.

Please see the independent bias audit report covering our use of Covey here.

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