Executive Driver & Security Specialist

Strategic Group; Calgary; On-site; CAD 60,000 - 90,000; Full time

Benefits offered by this job

Extended health and dental benefits

Company events

Flex days

Job summary

Strategic Group is seeking an Executive Driver & Security Specialist in Calgary, AB. The role provides secure transportation, executive escort, and personal protection for our leadership, with duties expanding to security reviews of properties when not actively protecting executives.

This full-time position requires a flexible 40-hour schedule, weekend and evening availability, and a high level of discretion. Candidates must maintain a clean driving record and pass background checks.

Qualifications

• Valid Class 5 driver's license with a clean driving record.
• Relevant experience in executive protection, law enforcement, military, protective services, private security, or a related field.
• Strong knowledge of personal security, situational awareness, risk assessment, de-escalation, and safe driving practices.
• Sound judgment, discretion, professionalism, and the ability to remain calm under pressure.
• Strong communication, observational, and problem-solving skills.
• Ability to work independently, assess security risks, and recommend practical improvements.
• Ability to work a flexible 40-hour schedule based on executive and operational requirements.
• Ability to pass a criminal background check, reference check, and driver's abstract review.

Responsibilities

• Provide personal security, escort, and professional driving support to designated members of the executive team.
• Maintain situational awareness during travel, meetings, appointments, events, public engagements, and other executive activities.
• Assess potential risks related to routes, destinations, surroundings, and changing conditions, and take appropriate preventative measures.
• Plan safe and efficient travel routes, including alternate routes where appropriate, based on traffic, weather, construction, events, and other considerations.
• Support safe arrivals, departures, airport transfers, and movement between locations.
• Respond appropriately to security concerns using sound judgment, de-escalation techniques, and established protocols.
• Maintain a discreet and professional presence that supports executive safety without unnecessarily disrupting normal activities.
• Ensure assigned vehicles are clean, safe, fueled, maintained, and operationally ready, including required emergency equipment and supplies.
• Conduct security reviews of company properties and active construction sites when executive protection and transportation support is not required.
• Identify significant physical-security vulnerabilities, deficiencies, and areas of elevated risk.

Skills

Executive protection

Personal security

Professional driving

Risk assessment

Job description

Executive Driver & Security Specialist

Join Our Team at Strategic Group

Ready to grow your career with one of Canada’s leading privately held real estate companies? At Strategic Group, we create spaces where people, businesses, and communities thrive.

About Us

At Strategic Group, our purpose is simple: Learning. Growing. Having Fun. We bring this ethos to life by innovatively envisioning, creating, owning, and operating real estate that transforms spaces and redefines possibilities.

As a fully integrated real estate company, we specialize in owning, managing, leasing, developing, and re‑developing properties. Our entrepreneurial spirit and innovative thinking have made us a Canadian industry leader in office-to-residential conversions, completing more successful conversions than anyone else in the country. This focus is a driving force in our development business and reflects our commitment to creatively reimagining what’s possible.

Our real estate portfolio spans high‑end residential developments and commercial properties. Beyond real estate, our business interests include corporate finance and other industries, enabling us to deliver diverse and impactful solutions for our tenants, partners, and communities.

Guided by our mantra, “Creating value others can’t, by seeing what others don’t,” we take pride in crafting unique solutions that leave a lasting legacy.

Our Values

• Team Player: We foster a supportive, accountable, and drama‑free workplace where integrity and respect guide every interaction.
• Innovative: Creativity and unconventional thinking are at the heart of what we do, helping us uncover opportunities others might miss.
• Always Growing: We are tenacious and passionate, thriving on challenges and embracing learning as we pursue new opportunities.
• Optimistic: With a positive mindset and solution‑oriented approach, we tackle obstacles as opportunities to learn, grow, and have fun.

If you’re ready to join a team that thinks boldly, acts innovatively, and works collaboratively, we’d love to hear from you!

Position Overview

We are seeking a professional, discreet, and dependable Executive Driver & Security Specialist to provide secure transportation, escort, and personal security support to members of our executive team.

The role is primarily focused on executive safety, situational awareness, and professional driving. During periods when executive support is not required, the position will conduct security reviews of company properties and construction sites, identify significant vulnerabilities, and recommend improvements.

This is a full‑time, 40‑hour‑per‑week position requiring flexibility to accommodate executive schedules, including occasional early mornings, evenings, weekends, and changing priorities. A high degree of professionalism, confidentiality, judgment, and discretion is essential.

Key Responsibilities

Executive Protection & Transportation

• Provide personal security, escort, and professional driving support to designated members of the executive team.
• Maintain situational awareness during travel, meetings, appointments, events, public engagements, and other executive activities.
• Assess potential risks related to routes, destinations, surroundings, and changing conditions, and take appropriate preventative measures.
• Plan safe and efficient travel routes, including alternate routes where appropriate, based on traffic, weather, construction, events, and other considerations.
• Support safe arrivals, departures, airport transfers, and movement between locations.
• Respond appropriately to security concerns using sound judgment, de‑escalation techniques, and established protocols.
• Maintain a discreet and professional presence that supports executive safety without unnecessarily disrupting normal activities.
• Ensure assigned vehicles are clean, safe, fueled, maintained, and operationally ready, including required emergency equipment and supplies.

Property & Construction Site Security

• Conduct security reviews of company properties and active construction sites when executive protection and transportation support is not required.
• Identify significant physical‑security vulnerabilities, deficiencies, and areas of elevated risk.
• Assess existing security measures, including building and site access, surveillance coverage, lighting, parking areas, perimeter security, key and fob controls, visitor and contractor access, and emergency considerations.
• Recommend practical security improvements based on risk, urgency, operational impact, and feasibility.
• Document significant findings and communicate recommendations to the appropriate operational teams.
• Follow up on material security concerns and support the implementation of corrective measures where required.

Security Planning & Risk Management

• Support security planning for executive travel, meetings, events, and other activities.
• Conduct advance reviews of locations or environments when appropriate based on risk or complexity.
• Maintain awareness of emerging risks that may affect executive safety, company properties, or operating locations.
• Provide practical advice and recommendations to strengthen security practices and reduce identified risks.
• Support the development and continuous improvement of security procedures, travel practices, emergency‑response protocols, and operational standards.
• Assist with incident response, escalation, documentation, and post‑incident review as required.

Coordination, Confidentiality & Professional Standards

• Maintain strict confidentiality regarding executive schedules, residences, travel, business activities, personal information, and security arrangements.
• Coordinate effectively with executives, executive assistants, property teams, construction teams, vendors, event personnel, security providers, and other stakeholders.
• Communicate schedule changes, risks, incidents, and recommendations clearly and promptly.
• Maintain appropriate records of security reviews, incidents, vehicle requirements, and other relevant activities.
• Demonstrate professionalism, discretion, sound judgment, reliability, and accountability in all aspects of the role.

Work Schedule

This is a full‑time position averaging approximately 40 hours per week.

The nature of executive protection and transportation requires flexibility. Working hours will vary depending on executive schedules, travel, meetings, appointments, events, and operational requirements. The position may periodically require early mornings, evenings, weekends, or changes to the normal work schedule.

The organization will structure the role around a full‑time workweek while maintaining the flexibility necessary to support executive security and transportation requirements

Qualifications

• Valid Class 5 driver's license with a clean driving record.
• Relevant experience in executive protection, law enforcement, military, protective services, private security, or a related field.
• Strong knowledge of personal security, situational awareness, risk assessment, de‑escalation, and safe driving practices.
• Sound judgment, discretion, professionalism, and the ability to remain calm under pressure.
• Strong communication, observational, and problem‑solving skills.
• Ability to work independently, assess security risks, and recommend practical improvements.
• Ability to work a flexible 40‑hour schedule based on executive and operational requirements.
• Ability to pass a criminal background check, reference check, and driver's abstract review.

Our Culture & Benefits

At Strategic Group, we’re committed to helping you build a career you’re excited about. If you’re passionate about working with a dynamic, motivated team in a fast‑paced environment, please submit your resume and cover letter today, and join us in making an impact.

We are proud to be an equal opportunity employer and celebrate diversity in all its forms. Our inclusive workplace ensures every employee feels valued and empowered to bring their best self to work.

As part of the Strategic Group team, you’ll enjoy a competitive compensation package, including an extended health and dental benefits plan, company events, flex days, and more.

This position is based in Calgary, Alberta. Applicants must be located in Calgary or the surrounding area.

We appreciate all applications, however, only candidates selected for an interview will be contacted.