IT Onboarding Engineer

IT Onboarding Engineer

Company Overview

Dependable Solutions specializes in a wide range of services, including tailored IT services and solutions for small and medium businesses and their owners in Wisconsin, Iowa, and Minnesota.

Dependable is committed to providing each and every one of our clients with high quality service and support.

Principles that Guide Us

The following serve as a foundation for our relationships with each other and the actions we take in the world.

Of the things we think, say or do:

• Is it the truth?
• Is it fair to all concerned?
• Will it build goodwill and better friendships?
• Will it be beneficial for all concerned?

Position Summary

The IT Onboarding Engineer is a critical member of the Dependable Solutions team, responsible for guiding new clients through a smooth, professional, and thorough onboarding experience. This role owns the onboarding process end to end — from initial discovery and documentation through tool deployment, configuration, and handoff to our service team.

This position is ideal for a technically well-rounded IT professional with MSP experience who is organized, process-driven, and thrives in a client-facing environment. A company vehicle is provided for all business travel.

Education and Professional Experience

Associate Degree or equivalent experience required. Minimum 4-5 years of hands-on IT experience, with at least 2 years in an MSP or multi-client environment strongly preferred.

Professional and Personal Traits

• Must possess a high degree of flexibility and ability to work in constantly changing environments
• Must have exceptional verbal and written communication skills, including comfort communicating directly with business owners and decision makers
• Must demonstrate strong time management and organizational skills with the ability to manage multiple onboarding projects simultaneously
• Must be a problem solver with strong critical thinking skills
• Must have the ability to work effectively under pressure while maintaining a calm, professional demeanor
• Must be a self-starter who takes ownership without being micromanaged
• Must work effectively both independently and as part of a team
• Must have a strong documentation discipline — if it isn't documented, it didn't happen
• Must have a "let's get this done right the first time" attitude

Essential Duties and Responsibilities

• Lead new client onboarding from kickoff through successful handoff to the service team
• Conduct client discovery sessions to document infrastructure, users, applications, and business requirements
• Deploy and configure RMM, M365, Entra ID, Intune, and security toolsets according to Dependable standards
• Build and maintain accurate client documentation throughout the onboarding process
• Perform endpoint configuration and desktop remediation as part of the onboarding process
• Coordinate with senior engineers for complex infrastructure work (servers, firewalls, migrations) while maintaining overall project ownership
• Communicate proactively with clients throughout onboarding to set expectations and deliver a consistent, professional experience
• Conduct onsite visits to client locations across the Madison area and broader Wisconsin territory
• Identify and escalate technical issues to appropriate team members promptly
• Contribute to the continuous improvement of onboarding processes and documentation standards

Technical Skills

Required:

• Microsoft 365 administration (Exchange Online, Teams, SharePoint) — 2-3 years
• Microsoft Entra ID (Azure AD) and Intune/endpoint management
• Basic networking concepts (DNS, DHCP, VLANs, firewalls)
• Endpoint configuration and desktop support experience
• Experience with PSA or ticketing platforms

Preferred:

• Windows Server fundamentals
• Experience working in an MSP or multi-client IT environment
• Familiarity with cybersecurity tools and basic security configuration
• Documentation platform experience (IT Glue, Hudu, or similar)

Job Type: Full-time

Benefits:

• Company vehicle provided for business travel
• Health insurance
• Life insurance
• Paid time off
• Professional development assistance
• Referral program
• Retirement plan

Education:

• Associate (Preferred)

Experience:

• IT experience: 4-5 years (Required)
• Microsoft 365 Administration: 2-3 years (Required)
• MSP or multi-client IT environment: 2 years (Preferred)
• Networking fundamentals: 2 years (Preferred)

Work Location: Field-based, Madison area. Travel throughout Wisconsin required. No regular overnight travel expected.

Pay: $28.00 - $33.00 per hour

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Employee assistance program
• Flexible spending account
• Health insurance
• Life insurance
• Paid time off
• Professional development assistance
• Referral program
• Vision insurance

Work Location: Hybrid remote in Madison, WI 53717

Salary : $28 - $33