Account Executive

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?

We're already empowering the most innovative employers nationwide, including Benchling, Pave, Figma, and more, driven by strong inbound demand.

As a founding member of our sales team, your mission is to bend the curve on the number of customers who use Cocoon by not only building the playbook on sales, but also training our future team.

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-party sales in a highly consultative manner. You'll work closely with our broker partners to convert introductions, and our marketing team to convert inbound. Finally, you'll be laying the foundation for scaling our sales team as a function. You'll develop our sales process from the ground up, including how to articulate our value proposition, and the creation of our sales assets & tools. If you're the kind of person who not only loves sales, but also building playbooks and coaching 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. You'll also become an expert on our customers - where they are today, where they're going in 6-12 months, what they need to succeed in getting there.
A collaborator, builder, and coach: You'll build the playbook for what the sales team looks like at Cocoon and train future team members. You'll also set the culture for our team as one 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!
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
6-8 weeks of disability 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 compensation range for this role is $250,000 - $300,000 OTE 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. 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.
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