IT Director – Hands-On Operator (Hybrid / On-Site Required)

Company Overview

The Black Dog Tavern Company is rooted in a deep sense of community, a passion for maritime pursuits, and a zest for life. We pride ourselves on offering the finest products and serving exceptional food within welcoming environments. We are committed to attracting professional, energetic, and passionate individuals to join our dedicated team.

About the Role

We are looking for a hands-on IT leader —someone who can troubleshoot real-time issues, stabilize systems, and keep the business running without disruption.

This is an on-site, high-accountability role supporting a fast-paced, seasonal operation across restaurants, retail, and warehouse facilities.

This Role Is Not

• Not remote
• Not a purely strategic or oversight role
• Not managing layers of IT staff

This is a doer role—you are expected to solve problems directly and be present in the business.

What You’ll Do

• Own all IT across multiple locations (POS, networks, eCommerce, back office)
• Resolve issues quickly and independently—especially during peak season
• Manage and hold vendors accountable
• Maintain system uptime and reliability across all operations
• Lead system improvements and upgrades without disrupting the business

What We’re Looking For

• Proven hands-on IT leadership
• Experience supporting multi-location operations (retail, restaurant, or warehouse preferred)
• Strong troubleshooting instincts—you fix problems, not escalate them
• Willing to be on-site and fully engaged
• Thrives in a fast-paced environment where execution matters more than process

Bottom Line

If you prefer a structured corporate environment with layers of support and narrowly defined responsibilities, this role will not be a fit.

Pay: $90,000.00 - $115,000.00 per year

Benefits:

• 401(k)
• Dental insurance
• Employee discount
• Health insurance
• Paid time off
• Parental leave
• Vision insurance

Work Location: Hybrid remote in Mashpee, MA 02649

Salary : $90,000 - $115,000