Senior Systems Engineer

When you work at Whittlesey, you join a diverse team that provides today’s business leaders with leading assurance, advisory, tax, and technology services. 

Whittlesey is proud to announce that we have been named one of the “Best of the Best" Firms and one of the “Top 200 Firms” by INSIDE Public Accounting (IPA), an award-winning newsletter for the public accounting profession. IPA’s annual “Best of the Best” list ranks top accounting firms with superior financial and operational performance in the most recent fiscal year. 

We have an exciting career opportunity for a Senior System Engineer to join our Technology Advisory team. This position is a hybrid position. Hybrid team members alternate between working remotely at the office, or client locations. This model encourages collaboration and creativity while still providing team members with flexibility. 

Our Culture 

Whittlesey has the experience and expertise of a large, national firm with the responsiveness of a local firm. That means our team members have access to the resources necessary to develop their careers while also receiving personal coaching. From the Managing Partner on down, our leadership fosters an open-door policy. We are committed to providing expert service to our clients across all our service areas, and we know that can only be done by employing talented and driven individuals. 

Collaboration and community are key values in our culture. Whether you are new to the Firm or have been here for several years, we respect each team member’s unique talents and value their contributions. Whittlesey is dedicated to the communities where we live and work. We sponsor community-driven events throughout the year and encourage our partners and team members to become actively involved in volunteerism.

Benefits and Work-Life Integration 

Meeting your professional goals does not mean you must sacrifice your personal life, which is why we adhere to a culture of work-life integration. We offer our team members flexible work schedules depending on their department’s needs and a competitive paid time off program.

Whittlesey also offers a competitive subsidized benefit package that includes medical and dental coverage. Other benefits include LTD and life insurance, all paid entirely by the Firm, and a 401(k) plan that includes profit sharing.

What you will be doing 

• Serve as a Primary or Secondary Engineer for assigned clients to build strategic plans, from analysis to plan development, recommendations, and presentation


• Collaborate with Network Engineers and leadership to design, implement, and support local and wide‑area network solutions for clients


• Performs preventative maintenance on client computer systems as directed by Primary Engineers by following procedures and guidance to ensure clients systems are regularly maintained. 


• Lead and manage projects from planning and proposal through execution and completion, including coordinating timelines, resources, and client communication.


• Monitor, manage, and resolve service tickets from creation to completion, handling more complex troubleshooting and escalating tickets as appropriate.


• Perform and oversee preventative maintenance activities to ensure client systems meet firm standards for security, performance, and sustainability.


• Provide technical expertise to our team members and clients while staying updated on industry standards.


• Regularly travel to CT based client locations to troubleshoot problems or deploy hardware and software


• Provide after-hours emergency support and planned maintenance as needed


• Meet billable hour targets through project, support, and recurring work

What you must have 

• Associate degree in Information Technology or related field from an accredited college or university and/or equivalent years of experience


• Minimum two years’ experience working in a Microsoft Server Environment required


• Minimum two years experience managing SMB business network environments


• Preferred Certifications: CompTIA Security , CompTIA A , CompTIA Network , Vendor Specific certifications (e.g., VMWare, Sonicwall, Microsoft)


• Working knowledge of general firewall and routing concepts.


• Experience managing Microsoft 365 Environments


• Knowledge in Windows Server 2008-2025 and Active Directory


• Must have a valid driver’s license (or equivalent legal authorization to operate a vehicle)

Must have access to reliable transportation to travel to various office and client locations as required.

Whittlesey is dedicated to building a diverse and inclusive workforce, so we encourage you to apply even if you feel you may not be an exact fit. Qualified applicants will receive consideration for employment regardless of their race, color, religion, sex, sexual orientation, gender, gender identity, age, national origin or protected veteran status and will not be discriminated based on disability.

Join us and make a meaningful impact in a collaborative and innovative environment. Apply now to be part of our team!