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Cocoon

Cocoon

Sales & Business Development
USD 300k-300k / year + Equity
Posted on Sep 24, 2025

🚀 Build the future of employee leave

We’re bringing much needed simplicity to the complex world of employee leave. Today, the process is baffling: 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 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?

We're empowering the most innovative employers nationwide, including Lattice, Benchling, Angi and more; driven by strong inbound demand.

As a member of our sales team, your mission is to bend the curve on the number of customers who use Cocoon by enhancing our current sales playbook and collaborating cross functionally.

You'll be initiating conversations with people leaders and converting these conversations to signed customers. You'll develop an in-depth understanding of the buyer journey for people leaders, and lead multi-threaded sales in a highly consultative manner. You'll work closely with our broker partners to convert introductions, and our marketing team to convert inbounds. Finally, you’ll be collaborating closely with other AEs to enhance the sales playbook and continue scaling our sales team as a function. If you’re the kind of person who not only loves sales, but also building playbooks and collaborating with teams - we want to chat!

⚡️ You'd be a great fit if you are:

  • 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.
  • Come with the right experience: You have a track record of working as an AE >3 years, selling into the Mid-Market space, and comfortable sourcing outbound opportunities. You ideally have familiarity selling People-focused software.
  • A strong listener & relationship builder: You can build relationships at multiple levels of an organization from a Chief People Officers and CFOs to People Ops managers. You pick up on the details and care about each customer you work with - you know how old your customer's kids are, and what's top of mind for them at work.
  • Highly consultative: You’ll become a trusted advisor on leaves and the complex world of regulations & insurance surrounding leave to our customers as they scale.
  • A collaborator, builder, and coach: You’ll help to enhance the playbook for what the sales team looks like at Cocoon. You'll fit in with a sales culture that is highly collaborative where we learn from and coach each other.
  • Willingness to move with speed and conviction, row together, and get in the arena. These are our values and they are critical to being successful at a fast-paced startup.
  • Ability to work cross functionally: You are someone who not only works closely with your sales team, but collaborates across all teams to positively impact a company’s ARR.
  • Curious with a desire to learn and grow: You may or may not join us with previous experience in leave of absence but you’re interested in learning from your peers or deepening your existing knowledge. You’ve been an account executive before but you are always looking to grow deeper in your role.

Bonus: Experience in Leave of Absence (LOA) or People/HR Software space

🎁 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
  • Parental and medical leave
  • Flexible work schedule

The compensation range for this role is $300,000 OTE (50/50 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. Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.


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.