Operations and Implementation Specialist

Remote, US

šŸš€ Build the future of employee leave

Weā€™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 ā€” removing all of the friction that exists today for both employees and employers ā€” 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.

šŸ’ŖšŸ½ What will you do?

We are seeking a dynamic and adaptable Operations and Implementation Specialist to join our team and play a critical role in streamlining processes and building scalable runbooks in our fast-paced startup environment. The ideal candidate will possess strong problem-solving skills, attention to detail, and excellent communication (written and verbal) abilities. As an Operations and Implementation Specialist, you will collaborate with cross-functional teams to optimize processes, implement self-serve customers, and ensure operational efficiency and alignment with company objectives.

  • Ability to adapt to changing processes quickly and thrive in ambiguity 
  • Capability to identify gaps in processes or breakdowns in cross-functional collaboration
  • Operates with the highest attention to detail and efficiency
  • Clear and effective written and verbal communication with cross-functional teams and leadership team
  • Collaborate with senior team members and cross functional teams to execute on analyzed data to derive insights and inform decision-making
  • Efficiently manage projects and tasks to support operational objectives
  • Manage implementations for scaled customer accounts, driving efficiencies through standardized playbooks, milestone tracking, and clear internal handoffs.
  • Deliver customer-facing product education through self-serve resources, and scalable enablement strategies to drive early adoption and long-term success.
  • Analyze data and create KPIs to measure the efficiency of our implementation processes to translate into product improvements

āš”ļøYouā€™ll be a great fit if you: 

  • Have experience in High-Growth Startups, payroll startup or experience with HRIS systems is a plus
  • Are familiar with queue-based workflows
  • Growth mindset: see something, say something 
  • Bias to action: we want Cocoons to see a process and say: this can be better!
  • Have experience with leave of absence in a multistate capacity
  • Have empathy for the leave experience and intricacies of the steps involved 
  • Have experience evaluating, implementing, and using AI tools in day-to-day for operational efficiency. Creating and using agents to automate processes is a plus.
  • Are proficient in data analysis tools such as Metabase, Gsheets/Excel, Hubspot

āœ… Success looks like: 

  • Continuous Optimization and Improvement Initiatives
  • Efficiency and Innovation
  • Positive Customer Experiences
  • Strong Project Management Skills
  • Contribution to Company Growth

šŸŽ 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 $75,000.

At Cocoon, we believe that diversity, equity, inclusion, and belonging (DEIB) serve as the foundation for a successful team, product, and community. Weā€™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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