Customer Success Manager

United States, Remote

🚀 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?

As a Customer Success Manager at Cocoon, you’ll own the long-term success of our customers. You’ll partner with HR, Benefits, and Finance leaders to drive measurable value, secure renewals, and unlock growth through strategic cross-sell and upsell opportunities. You’ll also help them deliver a leave experience that’s thoughtful, compliant, and scalable.

You’ll guide customers through key moments from implementation to renewals and expansion to becoming a trusted advisor and strategic partner every step of the way.

  • Own the customer relationship post-sale: Build strong, consultative partnerships with a portfolio of accounts, becoming their go-to person for all things leave-related from onboarding through renewal.
  • Drive expansion and upsells: Proactively identify opportunities for cross-functional adoption (e.g. new teams, geographies, or policies)
  • Deliver measurable value: Use data and product insights to show ROI, surface impact, and guide renewal and expansion conversations.
  • Advocate for customers internally: Share feedback with Product, Operations, Support, and Sales teams to improve our offering and anticipate customer needs.
  • Lead strategic renewals: Prepare for and lead renewal conversations grounded in value delivered, usage insights, and future opportunities.
  • Identify expansion opportunities: Spot ways Cocoon can support additional teams, policies, or workflows and partner with Sales when it’s time to grow.
  • Build for scale: Help evolve the CS playbook, including lifecycle frameworks, success plans, and expansion workflows.


⚡️ You'd be a great fit if you are:

  • Revenue-minded and strategic: You can spot commercial opportunities, understand buying signals, and love working cross-functionally to drive growth.
  • A business savvy relationship builder: You’re comfortable engaging with everyone from Benefits Managers to CFOs to Cocoon’s internal stakeholders and know how to align Cocoon’s value with business goals.
  • An excellent communicator: You bring clarity, empathy, and confidence to every customer conversation both written and verbal and are comfortable navigating conflict with calm and professionalism, even in highly escalated situations.
  • Customer-first: You’re passionate about advocating for your customers and helping them solve real, high-impact problems.
  • Strategic and proactive: You think ahead, plan touchpoints thoughtfully, and bring ideas to customers before they ask.
  • Detail-oriented and dependable: You track moving pieces and follow through because your customers trust you to stay on top of what matters.
  • Curious and growth-minded: You’re excited to learn the intricacies of leave laws, insurance coordination, and the employer/employee experience.

Bonus If You Have:

  • Experience in HR tech, benefits platforms, or B2B SaaS.
  • A background working with high-growth or early-stage teams.
  • A background in identifying and executing on cross-sell and upsell opportunities.
  • Familiarity with building out playbooks or contributing to cross-functional process development.

🎁 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 $119,000.

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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