Armed Security Supervisor-in-Training in Kalamazoo, Michigan at Grey Dog Security LLC

About the Position & The "Grey Dog Way"

At Grey Dog Security, we are more than a security provider—we are an active, dedicated partner in the communities we serve. We believe in giving back, supporting our team, and maintaining a workplace culture built on integrity, mutual respect, and continuous professional growth. That is the Grey Dog Way—leading by example, upholding the highest standards of safety, and empowering our leaders to succeed.

We are seeking a high-caliber, motivated leader to join our operational team as an Operations Supervisor-in-Training in South Michigan. This crucial leadership role bridges field execution with site oversight. You will be entrusted with managing officer schedules, ensuring operational compliance, enforcing site security standards, and maintaining a visible, authoritative, and reassuring presence.

To excel in the Grey Dog culture, you must bring proven leadership qualities, a calm and decisive demeanor in high-pressure situations, strong verbal de-escalation skills, and a commitment to top-tier customer service. Because this role oversees high-security posts and dynamic operational sites, verifiable armed guard experience and an active Michigan Concealed Pistol License (CPL) are required.

Schedule & Compensation

• Salary Structure: $41,000/year during the initial training period, automatically increasing to $46,000/year upon successful completion of supervisor training.
• Schedule: Full-Time. Must have open shift availability across a 24/7 environment, including days, evenings, overnights, and weekends, to effectively support site rosters and address operational needs.

Key Responsibilities

• Operational Leadership: Lead by example on-site, ensuring all officers embody company standards, follow post orders, and deliver exceptional service.
• Roster & Schedule Ownership: Working with a master scheduler to proactively manage shift coverage and resolving call-ins to prevent unfilled posts.
• Site Compliance & Quality Control: Conduct regular site checks, audit performance, and ensure all safety rules, facility procedures, and operational standards are strictly met.
• Incident & Conflict Management: Respond calmly and decisively to site disturbances, alarms, or emergencies; utilize advanced verbal de-escalation techniques as the primary tool to resolve conflict.
• Armed Operations Oversight: Maintain absolute readiness and oversight regarding armed post protocols, ensuring firearms and protective gear are handled with extreme professionalism, strict legal compliance, and strictly as a last resort.
• Client & Team Communication: Serve as a reliable point of contact for officers, client management, and local law enforcement during active site incidents.
• Documentation & Reporting: Ensure accurate, detailed incident reports and site shift summaries are completed and escalated appropriately to leadership.

• Armed Guard Experience: Minimum of 1–2 years of verifiable experience as an armed security officer, law enforcement officer, or military security specialist.
• Licensing: Active and valid Michigan Concealed Pistol License (CPL) (or state equivalent permit for armed security duties) is strictly required.
• Leadership Background: Prior supervisory, team lead, or management experience in security, military, or emergency services preferred.
• Education & Age: High school diploma or GED required; must be at least 21 years of age (in accordance with state firearm/CPL regulations).
• Background & Screening: Must successfully pass a comprehensive criminal background check (felonies and certain misdemeanors disqualify) and drug screen.
• Flexibility & Mobility: Reliable personal transportation and open shift availability (days, nights, weekends) to support roster requirements.
• De-escalation & Communication: Demonstrated mastery of verbal de-escalation, conflict resolution, and customer service.
• Physical Capability: Ability to stand, walk foot patrols, and remain alert for extended periods in varying conditions.