Lead MSP Systems Engineer

Sidewerks supports multi-location restaurant and hospitality businesses where technology outages have real-world consequences. When a POS system goes down, revenue stops. When a network fails, an entire location can be impacted.

That's why we're looking for a Lead MSP Systems Engineer who thrives under pressure, enjoys troubleshooting complex issues, and can help elevate the engineers around them.

This is a hands-on role. You'll spend your time solving problems, supporting clients, mentoring technicians, and acting as a senior technical resource across multiple environments.

What You'll Do

• Serve as a senior escalation point for complex technical issues
• Troubleshoot networking, firewalls, VPNs, Wi-Fi, Microsoft 365, endpoints, and SaaS platforms
• Support restaurant technology environments including POS systems such as Toast, Aloha, Micros, and Xenial
• Communicate directly with clients during outages and critical incidents
• Mentor and coach Tier 1 and Tier 2 technicians
• Help maintain SLA performance, ticket quality, and operational standards
• Coordinate with ISPs, vendors, and third-party providers
• Support onboarding and stabilization of inherited client environments
• Participate in an on-call rotation - Every other week Mon-Wed

What We're Looking For

• Recent MSP experience (required)
• Experience supporting multiple client environments simultaneously
• Strong networking and troubleshooting skills
• Comfortable handling high ticket volumes and escalations
• Excellent communication and client-facing professionalism

Compensation

$115,000 – $140,000+ depending on MSP experience and technical depth

• Health, dental, and vision coverage
• 401(k) matching
• Paid time off
• Professional development support