Find career opportunities in the Headline world.


Director of IT Operations



IT, Operations, Education
Posted on Saturday, November 11, 2023

Are you a data-driven problem solver who is passionate about making a difference in the lives of others while contributing to a successful business? Join Carewell and be a part of a team that creates impactful solutions for caregivers and their unique challenges. We're looking for hardworking individuals committed to raising the bar and striving for impact, scalability, and simplicity. Build your career with Carewell, a category-defining business dedicated to making caregiving easier.

The importance of hiring a Director of IT Operations

We are seeking a seasoned Director of IT Operations, reporting to the CTO, to oversee and manage our company's technology infrastructure, with a particular emphasis on Google Workspace Enterprise, Apple computer asset management, and single-sign-on solutions. The ideal candidate will possess a strategic mind for security-focused practices and a friendly, business-forward manner. This role requires the capability to manage a fully remote business environment, ensuring smooth IT operations including asset management, help desk support, software cost management, and maintaining responsive service level agreements (SLAs). The Director of IT Operations will be integral in collaborating with all business units to manage and acquire new software services, ensuring quality assurance and control (QA/QC).

What you’ll do:

  • Oversee the management of Google Workspace Enterprise, ensuring its optimal performance, security, and utilization within the organization.
  • Manage a comprehensive Apple computer asset management program to support the organization’s hardware needs, lifecycle, and inventory.
  • Design and implement robust single-sign-on (SSO) solutions to streamline access to company resources while maintaining high security standards.
  • Develop and enforce security best practices across the organization to protect company data and infrastructure from cyber threats.
  • Exemplify a likable, business-forward approach, fostering strong relationships within the company to support IT needs and initiatives.
  • Manage the IT operations of a remote-only workforce, including network infrastructure, collaborative tools, and remote support strategies.
  • Oversee the IT asset management process, including procurement, maintenance, and disposal of IT assets in accordance with company policies and budgets.
  • Lead the help desk team to provide exemplary technical support and maintain responsive SLAs for internal and external stakeholders.
  • Control IT software costs by managing licenses, subscriptions, and negotiating with vendors to ensure cost-effective solutions.
  • Collaborate with every business unit to understand their technology needs and partner in the management and acquisition of new software services, ensuring they align with company objectives and IT strategy.
  • Ensure quality assurance and control in the deployment of new IT services and during ongoing operations.


  • SLA on help desk
    • Response < 2 hours
    • Closure < 2 days
  • On time delivery of new project execution
  • Budget adherence and cost reductions
  • Change management success rate (deployments without impacting downtime)
  • IT, security, and privacy training tracking and adherence
  • Compliance and audit readiness
  • Effective vendor management

What you’ll need:

  • Bachelor's degree in Computer Science, Information Technology, or a related field; Master’s degree is preferred.
  • Minimum of 10 years of experience in IT operations, with at least 5 years in a leadership role.
  • Expert knowledge of managing Google Workspace Enterprise and Apple computer assets.
  • Proven experience in implementing and managing single-sign-on solutions.
  • Strong foundation in security best practices and managing IT in a remote work environment.
  • Business acumen with a proactive and friendly management style.
  • Excellent communication and interpersonal skills.
  • Demonstrated ability to manage IT software costs and work within a budget.
  • Experience in establishing and maintaining responsive SLAs.
  • A track record of successful partnerships with various business units for IT service management and acquisition.

What we offer:

  • Competitive compensation
  • Health, dental, vision, life, and short-term disability insurance
  • 401(k)
  • 100% remote
  • Generous PTO and federal holidays off
  • Employee discount

About Carewell

Carewell is a category-defining business that is dedicated to providing the most trusted and reputable retail source for caregiving products. Our vast selection of expert-vetted products includes incontinence supplies, wound care, nutrition, mobility aids, and more, all available at the best prices with fast, reliable shipping. We are proud to have been recognized as one of the fastest-growing companies in the US, ranked on the Inc. 5000, and named one of the most customer-centric companies in the world by Forbes in 2022. At Carewell, we understand the importance of caregiving, and we strive to provide the highest quality products to help caregivers provide the best care possible for their loved ones.

As the number of older adults in the US grows, the need for caregiving solutions will only increase. By joining Carewell, you will have the opportunity to work in a space that is constantly evolving, with new challenges and opportunities for growth. We are committed to being architects of our own success, always striving to improve our teams, partnerships, and solutions to ensure impact, scalability, and simplicity. As a member of our team, you will have the opportunity to collaborate with like-minded individuals, using customer insights, data, research, and feedback to make decisions and create the most effective solutions. If you are ready to join a team of dedicated individuals who are committed to making a difference in the world, Carewell is the place for you.

Learn more about us in the Carewell Newsroom.

Carewell's mission is centered around creating a better world for care. We believe having diverse and inclusive teams is an integral part of carrying out that mission. Our increasingly diverse world is faced with complex care challenges that can best be solved through a diverse and inclusive workforce, community of partners, and stakeholders. Carewell is committed to equal opportunity, and we welcome and encourage all walks of life to come learn, grow, collaborate, and create a better world for care with us.