Sr. Help Desk Engineer

Vaco by Highspring; Town of Texas (WI); On-site; USD 65,000 - 90,000; Full time

Job summary

Vaco by Highspring is seeking a Senior Help Desk IT Support Engineer to support internal employees nationwide. You’ll own complex issues, provide guidance to junior staff, and ensure accurate ticketing and resolution documentation.

The role covers Microsoft 365 administration, AD/Entra ID, and cross-platform device management across Windows, macOS, iOS, and Android. You will collaborate with cybersecurity, networking, and infrastructure teams, drive automation opportunities via PowerShell/Power

Qualifications

• 5+ years of enterprise help desk experience with escalation duties.
• Experience administering Microsoft 365 and hybrid identity basics.
• Proven ability to troubleshoot complex hardware/software/network issues.

Responsibilities

• Provide escalation support for Level 2/3 Help Desk issues and guide juniors.
• Log and track all requests with clear troubleshooting and resolution notes.
• Administer Microsoft 365 services including Exchange Online and Teams.
• Troubleshoot email delivery, mail flow, SPF/DKIM/DMARC as applicable.
• Manage AD/Entra ID provisioning, MFA, CA, SSO and password resets.
• Deploy and manage desktops and devices using Intune, Autopilot, MDT.

Skills

Active Directory management

Dell hardware knowledge

File manipulation & shared folders

Windows & macOS experience

MS Office Macros

Diverse technologies

PC hardware build & troubleshooting

Microsoft Deployment Tool imaging

Enterprise antivirus experience

Enterprise VPN experience

Job description

As the Senior Help Desk IT Support Engineer, you will report to manager of the Help Desk. You will provide support to internal our employees and leaders in the financial services industry across the country. You will be the primary contact to personnel looking for technical assistance across multiple systems by phone, email, and in-person. You will be empowered to provide first class support and creative solutions to facilitate a productive operating environment for all our teams.

What You'll Do

• Enterprise Help Desk escalation support: 5+ years preferred.
• Handle and resolve complex user hardware, software, identity, access, Microsoft 365, endpoint, and network-related issues, escalating to relevant teams when appropriate while maintaining ownership through resolution.
• Serve as the primary escalation point for Level 2 and 3 Help Desk issues and provide guidance, coaching, and technical direction to junior team members.
• Accurately log, update, and track all support requests using the request tracking platform, ensuring troubleshooting steps, user communications, escalation notes, and resolution details are documented clearly.
• Administer and support Microsoft 365 services, including Exchange Online mailboxes, shared mailboxes, distribution groups, Microsoft Teams, OneDrive, SharePoint, calendar permissions, mobile email configuration, and mailbox delegation.
• Troubleshoot email delivery and mail-flow issues using message trace, Outlook diagnostics, transport-rule review, shared mailbox permission validation, and DNS-related analysis, including SPF, DKIM, and DMARC where applicable.
• Administer and support identity and access processes across Active Directory and Microsoft Entra ID, including user provisioning, deprovisioning, group membership, licensing, MFA, Conditional Access, SSO, password resets, account lockouts, and hybrid identity synchronization issues.
• Deploy, configure, image, reimage, troubleshoot, and lifecycle-manage desktops, laptops, mobile devices, and peripherals using approved endpoint management and provisioning tools such as Microsoft Intune, Autopilot, Microsoft Deployment Toolkit, and related platforms.
• Troubleshoot device enrollment, compliance, Defender health, Windows Update, Autopilot ESP, hybrid join, profile corruption, endpoint performance, and remote-management issues.
• Support Windows, macOS, iOS, and Android devices in corporate, remote, and office environments, including direct user support, remote troubleshooting, and hands‑on deskside assistance.
• Maintain accurate IT asset and inventory records, including hardware assignments, device ownership, stock levels, refresh planning, returned equipment, retired assets, procurement coordination, and lifecycle management activities.
• Partner with cybersecurity, networking, infrastructure, vendors, and business stakeholders to resolve complex incidents, implement approved changes, and ensure timely communication on support requests and project work.
• Conduct root cause analysis for recurring incidents and identify opportunities to reduce repeat tickets through automation, process improvement, better documentation, training, or system remediation.
• Support conference room and collaboration technologies, including Microsoft Teams Rooms, room PCs, audio/video peripherals, displays, docking stations, softphones, and high‑visibility executive meeting support.
• Research, test, and document patches, upgrades, service packs, device models, peripheral standards, and support tooling before broad deployment.
• Create, update, and maintain standard operating procedures, troubleshooting runbooks, knowledge base articles, onboarding/offboarding procedures, asset‑management workflows, and internal documentation to improve consistency and self‑service support.
• Identify and implement approved automation opportunities using PowerShell, Power Automate, Microsoft Copilot, and other approved tools to reduce manual support effort and improve service delivery.
• Perform physical support tasks such as setting up and rearranging conference rooms, assembling and configuring desks or workstations, moving equipment, managing peripherals, or pulling wires through ceilings as needed.
• Promote a positive, accountable, customer‑focused Help Desk environment while maintaining strong communication, professionalism, urgency, and follow‑through.

What You Bring

• Active Directory management
• Hardware knowledge for Dell workstations/laptops
• File manipulation, shared files/folders networking
• Experience supporting both Microsoft and Mac operating systems
• Experience with Microsoft Office Macros (creation and installation)
• Experience with multiple technologies including operating systems, wireless networks, security software, imaging software, and databases.
• Experience with PC hardware build and troubleshooting.
• Microsoft Deployment Tool imaging console
• Enterprise level Antivirus experience.
• Enterprise level VPN experience.

Determining compensation for this role (and others) at Vaco/Highspring depends upon a wide array of factors including but not limited to the individual's skill sets, experience and training, licensure and certifications, office location and other geographic considerations, as well as other business and organizational needs. With that said, as required by local law in geographies that require salary range disclosure, Vaco/Highspring notes the salary range for the role is noted in this job posting. The individual may also be eligible for discretionary bonuses, and can participate in medical, dental, and vision benefits as well as the company's 401(k) retirement plan.

Additional disclaimer:

Unless otherwise noted in the job description, the position Vaco/Highspring is filing for is occupied. Please note, however, that Vaco/Highspring is regularly asked to provide talent to other organizations. By submitting to this position, you are agreeing to be included in our talent pool for future hiring for similarly qualified positions. Submissions to this position are subject to the use of AI to perform preliminary candidate screenings, focused on ensuring minimum job requirements noted in the position are satisfied. Further assessment of candidates beyond this initial phase within Vaco/Highspring will be otherwise assessed by recruiters and hiring managers. Vaco/Highspring does not have knowledge of the tools used by its clients in making final hiring decisions and cannot opine on their use of AI products.

Equal Opportunity Notice

Highspring LLC (d/b/a Vaco by Highspring) and its parents, affiliates, and subsidiaries ("we," "our," or "Vaco by Highspring") are committed to the full inclusion of all qualified individuals and does not discriminate against any employee or applicant for employment because of race (including but not limited to traits historically associated with race such as hair texture and hair style), color, sex (includes pregnancy or related conditions), religion or creed, national origin, citizenship, age, disability, status as a veteran, union membership, ethnicity, gender, gender identity, gender expression, sexual orientation, marital status, political affiliation, or any other protected characteristics as required by applicable law. The company is also committed to ensuring that persons who need them are provided with reasonable accommodations; if an accommodation is needed to participate in the job application or interview process, please contact [e-mail].

Vaco by Highspring also wants all applicants to know their rights that workplace discrimination is illegal.

Representation Notice

By submitting to this position, you agree that you will be giving Vaco by Highspring the exclusive right to present your as a candidate for the foregoing employment opportunity. Additionally, you agree to be included in our talent pool for future hiring for similarly qualified positions. You further agree that you have represented information about yourself accurately and have not affirmatively misrepresented your qualifications. Lastly, you agree to maintain as confidential, to the fullest extent permitted by law, any information you learn from Vaco by Highspring about the position and you will limit disclosure of information about the position only to the extent necessary to perform any obligations in furtherance of your application. In exchange, Vaco by Highspring agrees to exercise reasonable efforts to represent you through all solicitation, job screening and resume dispersal.

For residents of Ontario, Canada only: to the extent the position for employment is not with Highspring or not otherwise noted as vacant above, candidate should be informed that this role is to replace a presently employed person at Vaco by Highspring's client.

Privacy Notice

Vaco by Highspring respects your privacy and are committed to providing transparent notice of our policies.

• California residents may access Vaco by Highspring HR Notice at Collection for California Applicants and Employees here.
• Virginia residents may access our state specific policies here.
• Residents of all other states may access our policies here.
• Canadian residents may access our policies in English here and in French here.
• Residents of countries governed by GDPR and UK GDPR may access our policies here.

Additionally, submissions to this position are subject to the use of AI to perform preliminary candidate screenings, focused on ensuring minimum job requirements noted in the position are satisfied. More details about Vaco by Highspring's use of AI can be found here (https://www.highspring.com/ai-use-notices/). Further assessment of candidates beyond this initial phase will be conducted by recruiters and hiring managers. Vaco by Highspring does not know and cannot opine on if its client's use of AI products in hiring.

Pay Transparency Notice

Determining compensation for this role (and others) at Vaco by Highspring depends upon a wide array of factors including but not limited to:

the individual's skill sets, experience and training;

licensure and certification requirements;

office location and other geographic considerations; and

other business and organizational needs.

With that said, as required by local law, Vaco by Highspring believes that the following salary range referenced above reasonably estimates the base compensation for an individual hired into this position in geographies that require salary range disclosure. The individual may also be eligible for discretionary bonuses and/or participation in medical, dental, and vision benefits as well as the company's retirement plan (or similar retirement benefits).