Box Seat Server Jobs in Wisconsin (NOW HIRING)

The Role

As our Senior Systems Engineer, you're the senior escalation point and the technical lead for network, server, cloud, and cybersecurity work across every client we serve. When a problem is hard, the stakes are high, and a real fix is needed, you're the person the team counts on.

You'll architect and manage secure hybrid environments, on-premises and in the cloud, for a client base that includes accounting firms, financial advisors, dental offices, manufacturers, nonprofits, and other professional services businesses. You'll lead security delivery through our Guardion platform and support our virtual CISO work.

You'll also be GoTech's lead for AI. That means using tools like Microsoft Copilot and Claude in your daily work, building agents and automations that take busywork off the team's plate, training our staff and our clients to use AI well, and making sure it's all done securely. If you're excited about putting AI to work in a real business, this is a rare chance to own that process from grounding to implementation.

This is a hands-on, client-facing role. You'll be in front of people often, in person, on the phone, and in training sessions. You'll own work that ranges from complex network and cloud projects to the everyday issues that keep clients running. If you want variety, ownership, and work that genuinely matters to the businesses depending on you, this is the seat.

For the right person, this role grows into a virtual CISO position as our security practice matures, with a longer path toward service delivery leadership.

What You'll Do

Architecture & Infrastructure
• Design, build, and manage secure hybrid infrastructure, cloud and on-premises, across a diverse client base.
• Architect Microsoft Azure and administer Microsoft 365, Entra ID, and Intune at an expert level.
• Manage servers, virtualization (Hyper-V and VMware), storage, switching, routing, firewalls, and wireless.
• Contribute to GoTech's technical standards and help evaluate emerging tech like SD-WAN, SASE, and zero-trust.

Cybersecurity & Guardion
• Lead security delivery through Guardion: endpoint protection, EDR, SIEM, MDR and XDR, and compliance monitoring.
• Own incident response, run security audits and risk assessments, and drive prevention.
• Support our vCISO engagements with risk assessments, roadmaps, and compliance readiness (NIST, CIS, ISO 27001, CMMC).

AI Leadership
• Use AI assistants daily to speed up troubleshooting, documentation, and scripting.
• Build and maintain AI agents and automations that take busywork off the team's plate.
• Train staff and clients on AI and assist in setting the guardrails that keep their information secure.

Clients, Escalations & the Team
• Act as the senior escalation point for the toughest network, infrastructure, and cloud problems.
• Work with clients in person, on the phone, and through training sessions.
• Translate complex technical topics, capabilities, and requirements to users, meeting them where they are.
• Pick up and resolve tickets alongside the L1 and L2 team across Windows and macOS.
• Assist with the mentorship of L1 and L2 technicians and help elevate the quality of our support to all of our clients.

Our Tech Stack

You'll work across a modern, best-in-class toolset every day. That includes an industry-leading PSA and RMM for service delivery and monitoring, enterprise IT documentation, the Microsoft 365 and Azure cloud stack with Entra ID and Intune for identity and endpoint management, a unified cybersecurity platform (SASE, EDR, SIEM, and managed detection and response), enterprise backup and disaster recovery, business-grade networking and firewalls, and cloud-based communications. Deep experience with tools in any of these categories is a real plus.

What We're Looking For

You don't need to check every box. If you bring a strong foundation and a real drive to grow, we want to hear from you.

The Must-Haves
• 6 or more years in network and infrastructure engineering, ideally at an MSP. Five years with strong certifications and MSP experience will be considered.
• Deep networking: routing, switching, firewalls, VPN, VLANs, and WAN, plus DNS, DHCP, and Active Directory.
• Expert Microsoft 365 and Entra ID, and solid Azure across VMs, storage, networking, and identity.
• Comfortable across Windows and macOS, virtualization, and backup and disaster recovery.
• A real security mindset: threat detection, incident response, and network hardening.
• Hands-on with AI assistants like Copilot, Claude, or ChatGPT, and eager to build agents and lead AI adoption.
• A strong communicator who's great with clients in person and on the phone, and confident delivering training.
• A valid driver's license and reliable transportation for client visits.

Certifications You Have or Will Earn
We'll invest in getting you certified, so bring what you have and we'll build from there.
• Microsoft: AZ-104, MS-102, MD-102, AZ-700, or SC-200
• CompTIA: Network+, Security+, Cloud+, or Server+
• Networking and security: Cisco CCNA or CCNP, Fortinet, or Sophos
• AI and security: Microsoft Copilot Studio experience, CISSP, or SC-100

Ready to Level Up?

Are you a Level 2 tech who reads that list and thinks "I'm close"? We want to hear from you. If you've got a strong MSP foundation, a genuine drive to grow, and most of what's above, tell us where you are and where you want to go. We'll invest in the training and certifications to help you grow into the full scope of this role.

Compensation & Benefits
• Salary: $80,000 to $110,000, based on your experience and what you bring to the team.
• Quarterly Bonus: Discretionary bonuses tied to company and personal goals, with company performance weighted higher.
• Healthcare (QSEHRA): A tax-free monthly allowance toward the individual health plan you choose. You pick the coverage that fits your life, and we fund it.
• Simple IRA with Match: We match up to 3% of your contributions. Free money toward your future.
• Company-Paid Life Insurance: Coverage on us.
• Unlimited PTO: Take the time you need. We trust our team.
• Paid Training & Certifications: We invest in your growth and cover the certifications and training that move your career forward.

About GoTech

GoTech is a small team with a deep bench. Together we bring decades of combined experience across networking, cloud, cybersecurity, and managed IT, led by founder Chris Gotstein, who has spent more than 25 years in the field. When you join us, you're joining people who know their craft and hold a high bar for the work.

Since 2013, we've helped small and mid-sized businesses across Eastern Wisconsin and Michigan's Upper Peninsula get more out of their technology while staying secure, through managed IT, our Guardion cybersecurity platform, and virtual CISO services.

We're autonomous by nature and collaborative when it counts, with direct access to leadership and a shared commitment to communication and exceptional client service. Our goal is simple: keep our clients' businesses running without interruption, and make every interaction with GoTech one they're glad they had.

Learn more at gotechitsolutions.com.

Work Setup

This role is based out of our Brookfield, WI office on a hybrid work schedule. You'll report to our Operations Manager and work alongside our growing team of engineers and technicians. Travel to clients and their work locations will be expected. These site visits will primarily be across Southeastern Wisconsin, with occasional trips to clients in Michigan's Upper Peninsula. Mileage is reimbursed. Like everyone on our service team, you'll take part in a rotating on-call schedule for after-hours and weekend coverage. This is a full-time, exempt, salaried position, and on-call is included in your compensation.

Veterans & Military Service Members

Military service members and veterans are strongly encouraged to apply. The technical skill, discipline, and leadership you built in the service are exactly the kind of foundation we value at GoTech.

How to Apply

To apply, submit your resume and a cover letter. Our process is straightforward:
• A brief introduction call to get acquainted and answer your questions.
• A technical interview with our Operations Manager.
• A final interview with our President, Chris Gotstein, and a few team members.

We review applications on a rolling basis and reach out promptly to qualified candidates.

GoTech IT Solutions is an Equal Opportunity Employer. We consider all qualified applicants without regard to race, color, religion, sex, national origin, age, disability, veteran status, or any other characteristic protected by federal or state law.

GoTech IT Solutions is a managed IT services and cybersecurity company protecting small and mid-sized businesses across Eastern Wisconsin and the Upper Peninsula of Michigan. Our founder is an Amazon best-selling author on cybersecurity. We are built on honest communication, proactive service, and a genuine commitment to our clients' success. We are growing aggressively into new markets across two states.

We work with businesses that understand the value of technology and are looking for a trusted partner to handle everything from managed IT services and compliance to cybersecurity and vendor management. Whether it’s proactive support, cloud services, disaster recovery, or helping navigate complex technology decisions, GoTech is the go-to IT team for organizations who want results without the “tech talk”.

At GoTech, we do things differently. We’re not just another help desk — we become our clients’ technology partner. That means no outsourcing, no “geek speak,” and no waiting days for support. Our guaranteed response times, seasoned technicians, and personal approach set us apart. Clients value that we’re proactive, not reactive — always working behind the scenes to prevent issues before they impact productivity.
What truly defines us is our commitment to integrity, reliability, and service. We're a faith-based company that prioritizes long-term relationships with our clients and team. Our culture is rooted in five core values: Integrity, Excellence, Employee Development, Community Impact, and Trust. We are always striving to improve, educate, and uplift both our clients and our staff.

We also make sure our team members have the tools and environment they need to succeed and grow. If you’re looking to work for a company where your contributions matter, your voice is heard, and your career can grow with a company that’s going places — GoTech IT Solutions might be the place for you.