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IT Specialist



IT, Education
Boston, MA, USA
Posted on Wednesday, September 13, 2023

Openly is rebuilding insurance from the ground up. We are re-envisioning and enhancing every aspect of the customer experience. Doing this requires a rapidly growing team of exceptional, curious, empathetic people with a wide range of skill sets, spanning technology, data science, product, marketing, sales, service, claims handling, finance, etc.

Now is the perfect time to join the journey. Here’s why

  • It’s working. We’re in multiple states and on our way to operating countrywide. We have thousands of agents selling our product and millions of dollars of annual customer premiums.
  • We’re well-backed & stable. We closed our $75M Series C fundraise. We are supported by some of the top investors globally, including Google’s “Gradient” AI-focused fund, Obvious Ventures (Beyond Meat, etc.), and Advance Venture Partners.
  • It’s not too late! Despite this traction and stability, we’re still early enough in the journey that there’s time to make a real difference during Openly’s formative period.

If you’d like to understand more about Openly’s mission, consider checking out this video (https://vimeo.com/267654520) from a company pitch we gave several years ago at Techstars.

Job Details:

We are seeking a highly motivated and skilled IT Specialist I to join our dynamic IT team. The ideal candidate should possess 1-3 years of experience in IT support roles, a strong knack for troubleshooting technical issues, exceptional customer service skills, and a keen interest in asset management, IT inventory, and ticket triaging. The role requires a proactive individual who excels at time management and can work effectively both independently and as part of a team.

Key Responsibilities:

  • Provide first level technical support to end users, addressing hardware, software, and network issues promptly and effectively.
  • Diagnose and resolve technical problems through research, analysis, and troubleshooting, ensuring minimal downtime and disruption to users.
  • Collaborate with team members and other departments to escalate complex issues to higher level support or appropriate personnel.
  • Deliver exceptional customer service by effectively communicating technical solutions in a clear and understandable manner to nontechnical users.
  • Maintain accurate records of all user interactions, technical issues, and solutions in the ticketing system.
  • Triage incoming support tickets, assessing their urgency and impact, and assigning them to appropriate team members for resolution.
  • Assist in managing IT assets and inventory, including shipping, procurement, deployment, tracking, and disposal of hardware and software resources.
  • Perform routine hardware and software audits to ensure compliance with organizational policies and licenses.
  • Contribute to the development and improvement of IT processes and procedures to enhance overall efficiency and effectiveness.
  • Provide basic training and guidance to end users on using various hardware and software applications.
  • Prioritize and manage tasks effectively to meet established service level agreements (SLAs) and project deadlines.
  • Provide support to both macOS and Windows environments, including Windows applications on macOS through tools like Parallels Desktop.


  • Bachelor's degree in Information Technology, Computer Science, or related field, or equivalent work experience.
  • 1-3 years of experience in IT support roles, with a strong focus on troubleshooting technical issues.
  • Proficiency in diagnosing and resolving hardware, software, and network problems.
  • Excellent customer service skills with the ability to communicate technical concepts to nontechnical individuals.
  • Basic understanding of asset management principles and IT inventory control.
  • Experience with ticket triaging and assigning support tickets based on urgency and impact.
  • Strong organizational and time management skills, with the ability to prioritize tasks and manage multiple responsibilities concurrently.
  • Familiarity with ITIL principles and IT service management frameworks is a plus.
  • Technical certifications such as CompTIA A+, Microsoft Certified: Modern Desktop Administrator Associate, or equivalent are advantageous.
  • Proficiency in using IT ticketing systems and remote support tools.
  • Strong problem solving abilities and a proactive approach to identifying potential issues.
  • Experience with macOS and Windows environments, including knowledge of running Windows applications on macOS using tools like Parallels Desktop.
  • Ability to work effectively both independently and collaboratively in a team environment.
  • Excellent verbal and written communication skills.


This position is a Hybrid work model, the role requires onsite presence 2-3 days a week in our Back Bay, Boston office, with the flexibility to work remotely on other days.

Benefits & Perks

  • Competitive salary, corporate bonus program, equity position in a start-up company
  • Company-sponsored medical, dental, vision insurance plans, short-term and long-term disability, life insurance, 401k with corporate contribution, and FSA plan
  • Company-paid 12 weeks parental leave policy
  • The company fully embraces the “work-from-anywhere in the US” mentality, even before COVID restrictions.
  • Paid Time Off
  • Fun, fast-paced, startup environment

U.S. Citizens, Green Card Holders, and those authorized to work in the U.S. for any employer and currently residing in the US will be considered.

Openly is committed to equal employment opportunity and non-discrimination for all employees and qualified applicants without regard to a person's race, color, sex, gender identity or expression, age, religion, national origin, ancestry, ethnicity, disability, veteran status, genetic information, sexual orientation, marital status, or any characteristic protected under applicable law. Openly is an E-Verify Employer in the United States. Openly will make reasonable accommodations for qualified individuals with known disabilities under applicable law.