Director of IT and Infrastructure

Northampton, MA

Reporting to the President, the Director of IT and Infrastructure is an integral part of the company’s leadership team and is accountable for design, implementation, operation, and management of CheckWriters on premise and cloud infrastructure. The role is a vital leader of a growing team and must be a self-starter, possessing the ability to quickly understand complex situations and manage effective solutions across a diverse landscape of technology, software, services, staff, and customers.

CheckWriters is a payroll and HR services company focused on elevating every step of the customer experience. From customer interactions with our team to our genuinely useful software that's designed to fit customer needs — we don’t just provide an excellent product. We have a team of experts who care about the details, and work continuously to ensure that the customer experience is the best of any payroll and HR provider. 

The primary responsibilities of this senior level role include:

  • Being accountable for Cloud and on-premise technology infrastructure/operations, including all aspects of Networking, Compute, Storage, SQL Databases, Backups, and cloud technologies leveraging AWS, VMWare, Azure, Office 365, Sophos, ArubaOS, and Veeam.
  • Having responsibility for virtual workspace solutions such as conference room technology, end user hardware, 3rd party end user software services, as well as collaboration and communication tools such as Zoom.
  • Managing the end-user computing environment (mobile and desktop), including upgrades, maintenance, and versioning of the OS build, as well as application installation automation and system configuration manipulation using both packaged tools and various Windows scripting languages.
  • Managing remediation and compliance with vendor patch updates and security vulnerabilities using ManageEngine.
  • Monitoring, identifying, and responding to information security risks to protect the enterprise’s IT assets (e.g., intellectual property, sensitive data, malware, intrusion detection, etc.) using CrowdStrike.
  • Being a primary contributor to Infrastructure Strategy and Roadmap evolution, specifically related to the definition and development of technology infrastructure strategies which are in alignment with organizational scalability and growth.
  • Providing Business Continuity/Disaster Recovery oversight to assure that appropriate plans are in place, updated as needed due to business, and environmental or regulatory changes and are exercised as defined.
  • Responsibility for IT risks/controls and accounting/finance processes specific to on premise and cloud-based infrastructure including SOC 1, SOC 2.
  • Managing and administering the company’s 3CX telecommunications infrastructure and its associated software, including call management systems, voice mail, interactive voice response, and voice conferencing systems. This includes installing, configuring, maintaining, supporting, and optimizing all telephone systems and services, voicemail, and voice conferencing environments.
  • Managing supporting vendors’ relationship, including negotiation of contracts, vendor performance, and services provided to CheckWriters. Review hardware and software acquisition and maintenance contracts and pursue master agreements to capitalize on economies of scale.

Our ideal candidate will have:

  • A bachelor’s degree in Computer Science, Information Systems, or equivalent background or experience.
  • 8+ years of progressive IT experience, preferably with a mid-size, multi-site organization or an organization experiencing growth in size and location.
  • Proven exceptional leadership skills, marked by poise, positive influence, and the ability to drive change.
  • Demonstrated ability to employ judgment and experience to make rapid and complex decisions with broad impact.
  • Results oriented with the ability to transform complex and complicated ideas into actionable steps and track related progress among many stakeholders.
  • Demonstrated ability to lead and drive infrastructure change and transformation programs.
  • Proven experience in overseeing the design, development, and implementation of IT infrastructure, applications, and related products.