Systems Administrator / IT Generalist – Bailey’s, Inc.
At Bailey’s, we are building something that lasts.
We are a family-owned, 51-year legacy company and North America’s most trusted outfitter for forestry and tree care professionals. Our brand is well known in the market, and that reputation has been earned over decades by pioneering trusted solutions delivered on time, with passion and positivity.
We are looking for a Systems Administrator / IT Generalist who wants to help us build real redundancy across our technology and business systems.
This role is not just about fielding tickets. It is about ownership — of infrastructure, security, and business-systems support — and about building the backup depth that lets our technology team operate sustainably.
If you believe success comes from strong teamwork and collaboration, and you value structure, accountability, and continuously improving how things work, you will fit well here.
This role reports directly to, Chief Revenue Officer.
Who We Are
Vision: North America’s most trusted outfitter for forestry and tree care professionals.
Mission: We serve forestry and tree care professionals with reliable, high quality solutions delivered on time and strengthened through committed partnerships.
Purpose: We exist to inspire and empower our customers, partners, and employees to grow, succeed, and prosper together.
Brand Promise: Trusted Solutions. Delivered on time.
What This Role OwnsIT Infrastructure & Help Desk
- Serve as first-tier IT help desk — tickets, device setup, user onboarding and offboarding, and routine troubleshooting
- Own day-to-day support and lifecycle tracking for company-issued equipment, including workstations, laptops, printers, warehouse tablets, and peripherals
- Review backup and monitoring alerts, follow documented runbooks, and escalate as appropriate
- Maintain asset tracking and lifecycle management in Snipe-IT
- Assist with network, server, and infrastructure projects, including identity and access management, endpoint protection, and multi-factor authentication enforcement
- Provide cross-trained, genuine on-call redundancy for network, server, and server-room emergencies
ERP & Business Systems Backup
- Serve as a capable backup SAP Business One administrator — user management, basic configuration, report execution, and routine system support
- Own general reporting functions within SAP B1 and MicroStrategy, including standard report creation, maintenance, and deployment
- Support bWeb and LISA administration at a maintenance and user-support level
- Assist with system fixes and operational troubleshooting across the ERP stack
- Serve as the on-site point of contact for ERP-adjacent issues
Operational Continuity
- Create and maintain IT documentation, procedures, and recovery runbooks
- Act as a secondary technical point of contact for vendors, service providers, and escalations
- Support technical controls tied to regulatory and security requirements (including PCI-DSS, data privacy, and vendor access) without assuming legal ownership
What Success Looks Like
- Help desk tickets are resolved quickly, and routine requests no longer bottleneck on senior staff
- Bailey’s IT and ERP leads can each take a full, uninterrupted vacation without disruption
- SAP B1, bWeb, LISA, and MicroStrategy reporting requests are handled at the appropriate level without unnecessary escalation
- Documentation and runbooks exist for critical systems and recovery scenarios
- On-call coverage is genuinely shared rather than concentrated in one or two people
Must Haves
- SAP Business One experience — proficient and growing
- Magento experience
What We’re Looking For
- Hands-on IT generalist experience — networking, servers, endpoint support, identity and access management
- Exposure to, or willingness to learn, bWeb, LISA, or similar ERP/warehouse systems
- Comfort serving as the on-site backup across two technical domains rather than a single specialist track
- Strong attention to detail and follow-through
- Ability to manage multiple priorities without losing structure
- Someone who brings clarity, not complexity
Why Bailey’s
This is a role where you can actually make an impact.
You will work directly with leadership, help shape how we operate, and build systems that support long-term growth.
We are a family-owned business with a 50+ year legacy, and we continue to evolve while staying grounded in what built our reputation.
We value people who take ownership, follow through, improve what they touch, and care about the outcome.
If you’re looking for a role where you can build resilience into a growing technology stack and help build something meaningful, we should talk.
Pay: $59,000.00 - $78,000.00 per year
Benefits:
- 401(k)
- 401(k) matching
- Dental insurance
- Employee discount
- Flexible schedule
- Health insurance
- Life insurance
- Vision insurance
Work Location: In person
