Executive Assistant to the CEO

Orlando, FL

Full Time

Executive Operations

Experienced

Executive Assistant to the CEO – Job Responsibilities

As the Executive Assistant to the CEO at OneRail, you will play a critical role in supporting the company’s executive leadership by ensuring efficient operations, seamless communication, and strategic alignment across the organization. This position requires exceptional judgment, discretion, and organizational skills in a dynamic, high-growth tech and logistics environment.

Core Responsibilities

Executive Support & Coordination

Manage the CEO’s complex calendar, including scheduling internal and external meetings, investor engagements, customer discussions, and travel.
Prioritize and coordinate requests to ensure the CEO’s time is aligned with strategic priorities.
Act as the primary point of contact for the CEO, representing OneRail with professionalism in all interactions.
Prepare briefing materials, meeting agendas, and follow-up action items to support efficient decision-making.
Maintain confidentiality and handle sensitive information with discretion.

Communication & Relationship Management

Coordinate with OneRail’s leadership team, board of directors, and key external partners to ensure smooth communication flow.
Support internal and external communications, including executive updates, investor relations materials, and press or event coordination.
Foster strong relationships across departments to promote collaboration and alignment with company goals.

Operational & Strategic Support

Partner with the CEO to track strategic initiatives, ensuring progress and timely completion.
Assist in preparing materials for board meetings, investor updates, and strategic planning sessions.
Support special projects and research initiatives as directed by the CEO, including due diligence, data collection, and reporting.
Anticipate the CEO’s needs and proactively manage priorities to maximize effectiveness.

Event & Travel Management

Coordinate detailed travel logistics, including itineraries, accommodations, and meeting coordination.
Support OneRail leadership offsites, board meetings, and key corporate events.

Culture & Leadership Support

Serve as a culture ambassador, embodying OneRail’s values of innovation, integrity, and customer success.
Help organize leadership communications, recognition initiatives, and internal events.
Ensure the CEO’s engagement and visibility across teams by coordinating appearances, town halls, and key communications.

Requirements:

10+ years of executive administrative experience supporting C-level executives (experience in a fast-growth SaaS or logistics company preferred).
5+ years managing a Board of Directors with 10+ members
Proven ability to manage multiple priorities with precision, urgency, and confidentiality.
Strong written and verbal communication skills.
High emotional intelligence, professionalism, and discretion.
Proficiency in Microsoft Teams, Slack, and modern productivity tools.
Ability to thrive in a fast-paced, entrepreneurial environment.

Note: This role falls under Comp Band 4 with the annual base compensation is expected to be between $70,000 to $85,000.

About OneRail

OneRail is a leading omnichannel fulfillment solution pairing best-in-class software with logistics as a service to provide dependability and speed to help businesses meet their delivery promise. With a real-time connected network of 12 million drivers, OneRail matches the right vehicle for the right delivery so brands lower expenses and increase capacity to rapidly scale their businesses. This people-plus-platform approach features a 24/7 USA-based exceptions team who maintain a 98% on-time delivery rate. By optimizing fulfillment processes, reducing costs and improving order accuracy with store-shelf-to-doorstep visibility, OneRail is committed to empowering clients and improving the customer experience.

OneRail was named to the Deloitte Technology Fast 500™ two years in a row, was ranked 19th in the 2025 FreightTech 25, named for the fifth year in a row to the FreightTech 100, was honored as one of Inc. magazine’s Best Workplaces 2023, was listed on Forbes’ lists of America’s Best Startup Employers for the last three years, was named to the Inc. 5000 two years in a row and was selected as the Last Mile Company of the Year for the 2024 SupplyTech Breakthrough Awards. To learn more about OneRail, visit OneRail.com.

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