Two Chicks With A Side Hustle

Employer: Ease – Enrollease

About Ease:

Ease is the #1 rated benefits administration and HR software for businesses with 2–250 employees, powered by insurance brokers. 70,000+ employers trust Ease’s innovative SaaS service model to set up and manage benefits, onboard hires, stay compliant and offer their employees one destination for all their human resources information. Headquartered in San Francisco with offices in New York, Las Vegas, and Omaha, Ease was recently ranked number 57 in Forbes 2020 list of the top 500 startup employers in America.

Ease video

We are seeking candidates with a strong aptitude for troubleshooting and problem solving in addition to a focus in math. Experience in the health insurance industry is preferred. Prior SaaS experience is a plus.

We use a number of software applications, including our proprietary HR and benefits platform, on which you will be trained to support and guide our customers. You should have technical experience navigating and troubleshooting online applications and with spreadsheets.


  • Resolve Connections inquiries received via phone, web, email, and internal ticketing system, in a timeframe consistent to department and team service levels and goals.
  • Work collaboratively with customers and various internal resources to achieve desired results. Cross-functional teams include Product, Marketing, Training, Implementation, CSM, and Engineering teams.
  • Work collaboratively with carrier partners to resolve connection issues.
  • Resolve complex technical EDI and API errors from file transfers and assist customers with carrier communications.
  • Own and address customer needs and product issues from inception to resolution, including customer onboarding/development, diagnosing/resolving technical issues, and escalation support.
  • Identify and analyze upsell opportunities with customers and communicate details to appropriate stakeholders.
  • Maintain and create detailed documentation through logging of support cases, email, and knowledge base articles for customer and internal use.
  • Reports to the Sr. Manager of Connection Support.


  • 1-3 years of experience in a customer-facing role.
  • Experience with benefits i.e., medical, dental, vision preferred.
  • Strong communication and interpersonal skills are a must, including exceptional phone and written skills.
  • Strong troubleshooting and problem solving skills.
  • Effective organization and time management skills.
  • Strong customer focus and ability to manage and exceed customers’ expectations with every interaction.
  • Self starter with the ability to work independently in a remote environment.
  • Experience with Google Suites, Salesforce and Microsoft Excel preferred.
  • Knowledge of Atlassian, Jira and Confluence helpful.