🚀 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 Customer Success Manager, you’ll be enabling our customers like Figma, Benchling, & Affirm to go live with their first leaves, and as they grow with us, become our greatest evangelists.

You’ll be guiding our customers through the onboarding process to ensure their first employee who takes leave through the product finds it delightfully simple. When challenges arise, how you resolve these challenges builds even stronger trust with the HR & People leaders you work with. Along the journey, you’ll continuously deliver value to our customers by becoming their trusted advisor and demonstrating the value of Cocoon. Chief People Officers will look to you for advice on how their leave policy can be a powerful tool for retention & recruiting. Benefits Directors will turn to you on how to scale as the company grows. You’ll be a trusted ear for finance leaders on how our customers can offer an “employees first” leave policy and save money along the way.

When it comes time for our customers to renew - with the groundwork you’ve laid, they’re not only delighted to renew, but also can’t wait to refer us to their fellow HR & People leaders. And as we launch new products, they’re the first to pilot them with us.

Finally, you’ll be laying the foundation for scaling our customer success team as a function. If you’re the kind of person who loves to build playbooks - we want to chat!

⚡️ You'd be a great fit if you…

  • A relationship builder who is also comfortable with commercials: You can build relationships at multiple levels of an organization from a people ops manager to a CFO. At the same time, you’re as comfortable negotiating commercials as you are catching up on how daycare is going for our CPO’s toddlers.
  • A superb verbal & written communicator: You speak & write clearly, concisely, and with empathy. You are able to adapt your communication in a variety of situations and with a wide range of customer personas.
  • A creative problem solver: You think creatively about how to tackle first of kind problems our customers encounter - and proactively bring ideas to our product & eng teams.
  • An advocate for our customers: You advocate for our customers with our internal team by sharing feedback & insights to our product & engineering teams, as well as to our user support, sales, and marketing teams - all with the goal of continuously improving the experience for our customers and our end users - the employees they care about.
  • Excited to develop deep domain & customer expertise: You’ll become a trusted advisor on leaves and the complex world of regulations & insurance surrounding leave to our customers as they scale. You’ll also become an expert on our customers - where there are today, where they’re going in 6-12 months, what they need to succeed in getting there.
  • Exceptionally detail oriented: You are able to break down what's required for a customer to go-live into the play-by-play and seamlessly bring our customers along for the ride. You have a firm grasp on a wide range of important details in a customer's onboarding, and can project manage a complex launch to completion with rave reviews.
  • A strategist: You plan out the phases of how you’ll take a customer from deal signed to Cocoon evangelist. From onboarding, to day-to-day account management and business reviews, you orchestrate the right touchpoints to build up to a successful renewal and business expansion when the time comes.
  • A builder: You’ll build the playbook for what the Customer Success function looks like at Cocoon and train future team members.

🎁 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 and commuter benefits
  • Office setup and wellness stipends
  • 6-8 weeks of disability leave for birthing parents and 12 weeks of bonding for birthing and non-birthing
  • 4 weeks of flexible, paid compassionate leave
  • Flexible work schedule
  • Daily in-office lunches

The salary for this role is $127,500 OTE (80/20 split)

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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