Vice President, Software Engineering (Orlando)

Department: TechOps

Reports to: CTO

Location: (Remote, Hybrid or On-Site)

FLSA Status: Exempt (Salary)

Overview

As the Vice President of Engineering, you will lead a team of talented developers working together to transform final mile logistics and supply chain operations. This role will act as a key leader within the organization to help drive our development team. Success in this position comes from a highly collaborative approach with deep knowledge of software and development scale. The VP of Engineering reports directly to the Chief Technology Officer (CTO).

Responsibilities

• Partner with the CTO to create and implement a technology vision
• Partner with Chief Software Architect to identify scalability bottlenecks of our software, design future state architecture, and execute on plans
• Partner with client relationship managers, executives, and project managers to ensure that customer maintenance, project development, and new customer implementation needs are aligned with team-resources and priorities.
• Own the rollout, adoption, and continuous evolution of OneRail's AI-augmented software development lifecycle — including agent-assisted coding, code review, PR readiness, and cross-pod coordination tooling — ensuring engineers across all pods are equipped, trained, and accountable for using these capabilities effectively
• Define and operationalize the metrics that measure AI-augmented delivery outcomes (e.g., throughput, change failure rate, review cycle time, agent-assisted PR quality, and developer leverage), and use those measurements to drive iteration on tooling, process, and pod-level practices
• Partner with the CTO and Release & Risk pod to evolve quality gates, governance, and guardrails as AI tooling expands across the SDLC, ensuring velocity gains do not come at the expense of reliability, security, or auditability
• Act as supervisor to all technical leads, who support our product delivery teams
• Recruit and retain top-tier product delivery talent

Qualifications

• 10+ years proven and decisive senior leadership experience in full‑lifecycle software development, build and operations of complex systems
• At least 10 years of total software development contributor experience
• Experience leading and motivating high‑caliber technical specialists and leaders
• Background of full engineering leadership responsibilities, a demonstrated track record of successful business results and deep engineering development skills, with a strong customer focus
• Proven understanding of business principles and how engineering decisions impact financial performance
• Drive data‑supported decisions with a sense of urgency and possess the ability to instill that in others
• Passion for growing talent and identifying and rewarding impactful leaders.
• You have personally led the development and organizational changes required to scale both technology and team
• Strong knowledge of MySQL, Redis, and NoSQL systems and where to apply them
• Experience working within a hyper‑growth or scaling tech start‑up

Work Location

(Remote, Hybrid or On‑Site)

On‑Site Roles: This position is based at OneRail’s headquarters in Orlando, FL (ZIP 32819). While on‑site presence may be required, remote candidates will be considered, with preference given to those located in the Central Florida area.

Compensation Band 12: Min: $205,000 Q2: $231,389 Mid: $256,000 Q4: $282,000. Company target base salary: $205,000-$256,000.