Senior Chauffeur Jobs (NOW HIRING)

Benefits:

401(k)

Company car

Dental insurance

Health insurance

Help or transport service

Opportunity for advancement

Position Summary

Diamond Care Transportation is seeking an experienced, polished Senior Chauffeur to anchor the launch of our DC executive ground transportation service. This role provides safe, discreet, and professional transportation for executive, corporate, government, and affiliate-network clients (Blacklane, Carey, GroundLink) throughout the District of Columbia and the broader National Capital Region. As our founding chauffeur in DC, this individual will set the on-road service standard for the brand and is positioned to grow into a Lead Chauffeur / Operations Lead role within twelve months. The position demands exceptional time management, route mastery, situational awareness, and a refined professional presence at all times. Employees are expected to uphold our core values of Fraternity, Reliability, Safety, Compassion, and Teamwork.

Essential Duties and Responsibilities

The essential functions include, but are not limited to the following:

Safely operate company executive vehicles (sedan, SUV, and premium van class) for point-to-point, hourly charter, and airport transfer service.

Provide concierge-level passenger service: door management, luggage handling, beverage and amenity setup, and discreet attention to passenger preferences.

Anticipate client needs and adjust routes proactively for traffic, weather, security considerations, and schedule changes.

Maintain immaculate vehicle presentation at all times — interior detailed, exterior washed, amenities stocked, no trash or personal items visible.

Conduct daily pre-trip and post-trip vehicle inspections; report mechanical, cosmetic, or technology issues immediately.

Operate digital dispatch and reservation platforms accurately; confirm trip details, log start/end times, capture mileage, and reconcile gratuities and tolls.

Comply with all DC Department of For-Hire Vehicles (DFHV) regulations, WMATC requirements, and applicable Maryland and Virginia for-hire regulations.

Communicate professionally and discreetly with clients, executive assistants, hotel staff, venue personnel, and affiliate-network dispatchers.

Handle client concerns or service issues calmly and resolve in a solution-oriented manner; escalate appropriately when needed.

Represent the Diamond Care brand uniform standard at all times: business attire, polished appearance, and conduct consistent with luxury hospitality.

Leadership track: contribute to driver onboarding, route development, and service playbook documentation as the operation scales. Train and mentor incoming chauffeurs.

Minimum Qualifications (Knowledge, Skills, and Abilities)

Minimum age requirement of 25

High School Diploma or GED required; some college or hospitality training preferred

Valid driver's license with clean MVR (no more than two minor violations in the past three years; no DUI/DWI within ten years)

Active DC Public Vehicle-for-Hire (PVH) Face ID license, or ability to obtain prior to start date — required

Three or more years of professional chauffeur experience in a Class-A market (DC, NYC, Boston, Miami, LA, London, or comparable)

Prior experience driving for executive, corporate, government, or VIP clientele required

Familiarity with affiliate-network platforms (Blacklane, Carey, GroundLink, Empire CLS, Addison Lee) strongly preferred

Prior dispatch, lead chauffeur, or operations supervisor experience preferred — this role is intended to grow into leadership

Working knowledge of DC, MD, and VA roadways, airport protocols (DCA, IAD, BWI), and high-traffic corridors

CPR and First Aid Certification preferred

Excellent interpersonal, customer service, and discretion skills

Strong time management, organizational, and digital tool proficiency

Ability to work independently, exercise sound judgment in unstructured situations, and represent the brand without supervision

Job Description

Refined professional presence and communication, comfortable interacting with executives and high-profile clientele

Exceptional discretion and confidentiality

Strong written and verbal communication

Comfortable using smartphones, dispatch apps, GPS systems, and reservation platforms

Self-directed, accountable, and motivated by craft and growth — not just completing trips

Physical Demands and Work Environment

The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this position. Reasonable accommodations may be made to enable individuals with disabilities to perform the functions.

Ability to sit for extended periods while driving, sometimes for several hours at a time, including back-to-back airport transfers and full-day charters.

Frequent standing during meet-and-greet, door service, and waiting periods at airports, hotels, and venues.

Frequent bending, lifting, and reaching to load and unload luggage, garment bags, and client equipment.

Ability to lift, push, and pull up to 50 lbs., including suitcases, golf bags, and event materials.

Capability to assist passengers entering and exiting vehicles with poise and professionalism.

Adequate vision and hearing to operate a vehicle safely, monitor surroundings, and interact with passengers.

Occasional exposure to inclement weather during pickup, drop-off, and door service.

Polished, client-facing environment. Low noise level. Frequent presence at upscale hotels, embassies, federal buildings, airports, and private residences.

Compensation

Salaried position. This is a salaried role, not hourly, reflecting the one-to-one relationship between the DC PVH Face ID, the assigned vehicle, and the chauffeur. You'll be entrusted with a dedicated executive vehicle and operate it as the founding driver of the DC service.

Competitive base salary, commensurate with experience and trajectory

100% pass-through of client gratuities (industry-standard 20% on direct-bill, plus all affiliate-network gratuities)

Trip-based performance incentives once volume baseline is established

Defined path to Lead Chauffeur / Operations Lead within 12 months for the right candidate

Medical, dental, and vision benefits via UnitedHealthcare (Level Funded through Paychex), effective the first of the month following the 90-day introductory period

Paid time off accrual, uniform allowance, dedicated parking provided

All vehicle operating costs (fuel, maintenance, registration, insurance, tolls) covered by the company

Work Schedule

The executive ground transportation market runs on demand windows rather than fixed shifts. Realistic availability looks like early-morning airport service, weekday business hours, evening events, and rotating weekend coverage. Total weekly working time typically sits in the 45–55 hour range, consistent with senior chauffeur norms in the DC market.

We're intentionally not prescribing a rigid weekly schedule in this listing. As the founding chauffeur, your perspective on what scheduling structure works best for an affiliate-network and corporate operation in DC will help shape how we set this up. Plan to discuss your preferred structure during the interview process — whether that's a five-and-on-call model, a rotational structure with a second driver, or another model you've seen work well in prior roles.

The assigned executive vehicle remains dedicated to you throughout your tenure.