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Security Supervisor - Full Medical, $100 Deductible

$25 per hour

The CW Security Group, LLC

MAUI SECURITY TEAM LEAD / SUPERVISOR

Signal Security of Hawaii

Position Type: Full-Time / Leadership
Department: Operations
Location: Maui, Hawaii
Reports To: Operations Leadership/ Owner & CEO

Lead With Accountability. Serve With Aloha.

Signal Security of Hawaii is seeking an experienced and dependable Maui Security Team Lead / Supervisor to help lead, support, and elevate our growing Maui security team.

This is a hands-on leadership position for someone who understands that great supervision means more than holding a title.

We are looking for a leader who is visible, responsive, organized, dependable, and willing to work alongside the team when needed. This individual will help ensure our officers consistently meet company expectations, client standards, post orders, reporting requirements, uniform standards, and our commitment to professional service.

The right candidate must be able to lead with confidence while treating employees, clients, residents, guests, and community members with respect and Aloha.

At Signal Security of Hawaii, we believe in:

Aloha in Service. Excellence in Security.

WHY JOIN SIGNAL SECURITY OF HAWAII?

Signal Security of Hawaii is a locally operated security company providing professional security services throughout Hawaii.

As our Maui operations continue to grow, we are looking for leaders who want to help build strong teams, create consistency, support our clients, and contribute to the continued development of our company.

Depending upon eligibility and position requirements, benefits and opportunities may include:

  • Medical Insurance: PPO coverage provided for all benefit eligible employees, with $100 annual deductible, $15 office visit copays & $25 urgent care visit copays. Optional coverage extended to spouses & eligible dependents through payroll deduction.
  • Employer-paid Life Insurance & AD&D: $20,000 benefit included in employee benefit package.
  • Vision Coverage: Included in employee benefit package. Optional coverage extended to spouses & eligible dependents through payroll deduction.
  • Dental Coverage: PPO dental plan option available through Humana for employee, spouse & eligible dependents through ACH payment.
  • Chiropractic, Naturopathic, Acupuncture and Massage Coverage: Included in employee benefit package. Optional coverage extended to spouses & eligible dependents through payroll deduction.
  • EAP/Employee-Assistance Program: Included in employee benefit package.
  • Disability/Income Protection Coverage (guaranteed-issue = everyone qualifies): Optional coverage available through payroll deduction (employee-only).
  • Voluntary Life Insurance (guaranteed-issue = everyone qualifies): Optional coverage available for employee, spouse & eligible dependents through payroll deduction.
  • Cash-Benefit Programs (to help pay everyday bills - guaranteed-issue = everyone qualifies): Optional coverages for injuries & illnesses available for employee, spouse & eligible dependents through payroll deduction.
  • Active&Fit Program: Included in employee benefit package.
  • Virtual Health Memberships (for humans and pets, with Rx benefits): Optional coverage available for employee, spouse & eligible dependents through payroll deduction.
  • Holiday pay for qualifying state and federal holidays based on eligibility
  • Tuition reimbursement and continuing-education opportunities
  • Expert-led Training & Career Development
  • Career Advancement Opportunities
  • Professional Development Assistance
  • Additional Benefit Contributions for Leadership Positions
  • Employee recognition programs
  • Employee referral program
  • Exclusive benefits for long-term employees
  • Opportunity to work directly with executive leadership
  • Opportunity to help shape the employee experience and culture of a growing Hawaii company

POSITION SUMMARY

The Maui Security Team Lead / Supervisor will provide day-to-day operational leadership and support for Signal Security of Hawaii personnel assigned throughout Maui.

This position serves as an important connection between frontline officers, company leadership, and our clients.

The Team Lead / Supervisor will assist with employee oversight, site inspections, coaching, training, scheduling support, incident response, report review, client communication, equipment accountability, and overall quality assurance.

This leader must be prepared to respond when problems occur and should not rely solely on phone calls or messages to manage the team.

The successful candidate will be expected to maintain a strong presence in the field and help ensure our employees have the direction, tools, information, and accountability necessary to perform successfully.

KEY RESPONSIBILITIES

Team Leadership & Employee Oversight

The Team Lead / Supervisor will help provide consistent leadership to Maui security personnel.

Responsibilities include:

  • Lead by example in professionalism, appearance, communication, attendance, and performance.

  • Provide daily support and direction to Security Officers and Patrol Officers.

  • Help employees understand site expectations, post orders, policies, and procedures.

  • Conduct employee check-ins and site visits.

  • Coach employees when performance improvements are needed.

  • Recognize employees who demonstrate strong performance and leadership.

  • Reinforce company expectations regarding attendance, punctuality, communication, reporting, and professional conduct.

  • Address minor employee concerns before they become larger operational problems.

  • Escalate significant employee-relations concerns to appropriate leadership or Human Resources.

  • Assist with corrective-action documentation when necessary.

  • Support new employees during their onboarding and introductory period.

  • Help identify employees with leadership potential.

  • Encourage teamwork, professionalism, accountability, and mutual respect.

Site Inspections & Quality Assurance

  • Conduct scheduled and unscheduled site inspections.

  • Verify employees are present, properly uniformed, alert, and performing assigned duties.

  • Ensure officers understand and follow current post orders.

  • Review Daily Activity Reports, incident reports, patrol reports, and other required documentation.

  • Identify incomplete, inaccurate, or poorly written reports and provide coaching when necessary.

  • Ensure equipment, site phones, vehicles, keys, access devices, and other company property are properly maintained.

  • Confirm client sites remain organized and professional.

  • Identify potential safety, security, staffing, or operational concerns.

  • Report significant concerns to leadership promptly.

  • Follow through on corrective actions until issues are resolved.

Scheduling & Coverage Support

Security operations require flexibility, and leadership must be able to respond when circumstances change.

Responsibilities may include:

  • Assist with maintaining appropriate staffing levels.

  • Monitor known coverage gaps.

  • Help coordinate shift coverage when employees call out.

  • Communicate staffing concerns to leadership.

  • Contact available employees when additional coverage is needed.

  • Assist with schedule adjustments as directed.

  • Help prevent unauthorized overtime whenever possible.

  • Support emergency and short-notice staffing situations.

  • Step into operational coverage when reasonably necessary and qualified to do so.

  • Ensure shift changes and coverage arrangements are properly communicated.

The Team Lead / Supervisor must understand that leadership in a 24/7 security environment occasionally requires flexibility outside traditional business hours.

Client Service & Communication

  • Maintain professional relationships with assigned clients.

  • Conduct routine client check-ins when requested.

  • Listen carefully to client concerns and ensure appropriate follow-up.

  • Communicate operational issues accurately and professionally.

  • Avoid making commitments outside the scope of authority.

  • Escalate significant client concerns promptly.

  • Assist with implementing updated client instructions.

  • Help ensure employees understand client expectations.

  • Maintain appropriate professional boundaries between employees and clients.

  • Represent Signal Security of Hawaii professionally at all times.

Incident & Emergency Response

The Team Lead / Supervisor may be required to assist during significant security incidents or operational emergencies.

Responsibilities may include:

  • Respond to sites when leadership assistance is required.

  • Assist officers during challenging incidents.

  • Ensure proper notifications are made.

  • Support emergency responders when appropriate.

  • Preserve professionalism during high-stress situations.

  • Ensure incident reports are completed thoroughly and promptly.

  • Review significant incidents for operational or training lessons.

  • Escalate critical incidents immediately according to company protocols.

  • Participate in post-incident reviews when requested.

Training & Employee Development

  • Assist with training new and existing employees.

  • Reinforce site-specific post orders.

  • Coach employees on professional report writing.

  • Reinforce situational awareness and officer safety.

  • Support customer-service and de-escalation expectations.

  • Help employees properly use company technology and reporting systems.

  • Reinforce chain-of-command expectations.

  • Identify training gaps and communicate them to leadership.

  • Participate in leadership meetings and company training sessions.

  • Help create consistency across Maui sites.

Mobile Patrol & Vehicle Oversight

Where applicable, responsibilities may include:

  • Conduct supervisory patrols.

  • Inspect company vehicles for cleanliness, safety, damage, and required supplies.

  • Ensure drivers follow company vehicle and safety expectations.

  • Verify vehicles are properly stocked and maintained.

  • Immediately report vehicle damage or safety concerns.

  • Reinforce safe driving expectations.

  • Review concerns regarding vehicle operation, GPS information, or assigned patrol responsibilities.

  • Help ensure company vehicles remain professional representations of the organization.

REQUIRED EXPERIENCE & QUALIFICATIONS

Previous professional security experience is required.

Previous supervisory, lead officer, management, military leadership, law-enforcement, loss-prevention leadership, or comparable operational leadership experience is strongly preferred.

Candidates must demonstrate:

  • Previous security experience.

  • Proven reliability and dependable attendance.

  • Strong leadership and communication skills.

  • Ability to supervise and coach employees professionally.

  • Strong situational awareness.

  • Sound judgment and decision-making ability.

  • Ability to remain calm during stressful situations.

  • Strong written communication and report-writing skills.

  • Ability to manage multiple responsibilities.

  • Strong attention to detail.

  • Ability to work independently.

  • Professional customer-service skills.

  • Strong problem-solving and critical-thinking abilities.

  • Ability to maintain confidentiality.

  • Ability to use mobile applications, reporting systems, email, messaging platforms, and other company technology.

  • Ability to follow and enforce company policies consistently.

  • Ability to work respectfully with employees from different backgrounds and experience levels.

  • Flexibility to respond to operational needs when necessary.

Candidates must meet all applicable requirements to legally perform security work in the State of Hawaii.

DRIVING REQUIREMENTS

Because this position may require travel between Maui client locations, candidates should possess:

  • A valid driver's license.

  • A safe and acceptable driving history.

  • Ability to safely operate company vehicles when assigned.

  • Willingness to conduct site checks during varying hours when needed.

THE LEADER WE ARE LOOKING FOR

The right candidate:

  • Leads from the front.

  • Does not ask employees to meet standards they are unwilling to meet themselves.

  • Shows up when needed.

  • Follows through.

  • Communicates proactively.

  • Takes responsibility.

  • Does not ignore problems.

  • Understands the importance of documentation.

  • Is comfortable having difficult but respectful conversations.

  • Treats employees fairly and consistently.

  • Maintains professional boundaries.

  • Avoids gossip and workplace drama.

  • Protects confidential company and employee information.

  • Works well independently.

  • Thinks critically before making decisions.

  • Understands the importance of client relationships.

  • Knows when an issue should be handled directly and when it should be escalated.

  • Can balance employee support with accountability.

  • Demonstrates Aloha while maintaining professional standards.

PERFORMANCE EXPECTATIONS

Success in this position may be measured through:

  • Employee attendance and accountability

  • Reduction in preventable coverage gaps

  • Quality of officer performance

  • Site inspection completion

  • Report quality

  • Employee communication

  • Training completion

  • Client satisfaction

  • Response to operational concerns

  • Timeliness of follow-up

  • Vehicle and equipment accountability

  • Employee retention

  • Quality-assurance results

  • Leadership presence

  • Ability to resolve problems before they escalate

  • Professionalism and dependability

OUR CULTURE

Signal Security of Hawaii is built around service, relationships, accountability, and Aloha.

Our core values include:

Aloha
Passion
Honesty & Integrity
Relationships
Serving

We expect our leaders to model these values every day.

For us, Aloha means approaching employees, clients, residents, guests, community members, and one another with respect, dignity, professionalism, patience, and genuine care.

Aloha does not replace accountability.

Strong leadership requires both.

READY TO LEAD?

If you are an experienced security professional who is ready to take the next step in leadership and help build a strong, professional, and dependable security team on Maui, we encourage you to apply.

Please submit your resume detailing your previous security and leadership experience .

Candidates whose experience most closely matches the requirements of the position will be contacted regarding the next step in the interview process.

Signal Security of Hawaii

Aloha in Service, Excellence in Security.

Signal Security of Hawaii is an Equal Opportunity Employer. Employment decisions are based upon qualifications, business needs, and applicable employment requirements without unlawful discrimination.

Vacancy posted 8 days ago
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