Head of Operations & Market Strategy

About Prestige Ride

Prestige Ride Services Inc. is a fast-scaling luxury transportation technology business serving customers throughout the United States. The company blends AI, automation, enterprise software, and a national affiliate model to provide premium chauffeur services without relying on a company-owned fleet.

As the business expands into new markets, it is looking for a senior operator who can create strong, repeatable systems and help shape the next stage of growth.

Role overview

This is a hands-on executive leadership role for someone who can help turn Prestige Ride into a top-tier luxury mobility brand. You will partner closely with the CEO and have visibility across core functions such as operations, dispatch, customer experience, affiliate partnerships, business development, technology, marketing, finance coordination, and AI-driven automation.

The position is designed for a builder, not a conventional operations manager. The ideal candidate will create processes, metrics, teams, and automation that can support growth at scale.

Key responsibilities

In this role, you will be expected to strengthen leadership execution across the business, improve operational performance, and help the company expand efficiently.

Executive leadership

• Design operating frameworks that can scale with the company.
• Create and maintain company-wide standard operating procedures.
• Develop dashboard reporting for key performance indicators.
• Guide and support department leaders.
• Raise execution quality across all business units.
• Deliver weekly updates and reporting to the executive team.

Operations

• Improve the efficiency of nationwide chauffeur operations.
• Streamline dispatch workflows and scheduling.
• Strengthen affiliate partner performance.
• Lower the rate of service breakdowns.
• Enhance the overall customer experience.

AI and automation

• Lead the adoption of AI across dispatch, CRM, customer support, finance, marketing, driver management, reporting, and quality assurance.
• Build and refine automation workflows using modern tools and AI systems.
• Apply AI to improve speed, consistency, and operational visibility.

Technology

• Collaborate with developers on mobile apps, internal CRM tools, customer-facing portals, driver portals, affiliate portals, and AI integrations.
• Bring a practical understanding of software product development and delivery.

Growth

• Support national expansion into new markets.
• Help improve profitability and reduce operating costs.
• Contribute to building a strong executive leadership bench.

Required background

The company is seeking someone with deep executive experience who has led complex teams and multiple functions in fast-moving environments.

• At least 10 years of executive leadership experience.
• Prior work as a COO, VP of Operations, Chief of Staff, or General Manager.
• Experience in transportation, mobility, SaaS, marketplaces, hospitality, logistics, or other high-growth technology businesses.
• Track record of managing teams of 50 or more people.
• Experience overseeing several departments at once.
• Solid financial acumen.
• Strong communication ability.

Preferred industry exposure

• Luxury transportation.
• Uber-like mobility businesses.
• Blacklane or similar ground transportation models.
• Ground transportation operations.
• SaaS marketplace companies.
• Enterprise software businesses.
• Hospitality.
• Logistics.

Success expectations

During the first 12 months, the selected leader is expected to improve operating efficiency, raise customer satisfaction, shorten response times, grow the affiliate network across the country, introduce AI into core workflows, build executive reporting systems, and establish strong operating procedures. The longer-term goal is to help position Prestige Ride as a leading AI-enabled luxury transportation platform in North America.

Leadership qualities

• Founder-style ownership and decision-making.
• Comfort using data to guide choices.
• Enjoyment of building systems from the ground up.
• Ability to thrive in a high-growth startup environment.
• Strong personal accountability.
• Proactive problem-solving approach.
• Deep commitment to operational excellence.

Compensation note

This role is intended to be treated as a founding executive position rather than a standard COO opening. The compensation structure should be highly competitive and may include performance-based bonuses. For the right candidate, a meaningful long-term equity or phantom-equity incentive tied to company growth may also be considered.

Location

New York, NY is preferred. The role can be performed remotely from anywhere in the USA, with travel as needed.