Principal Software Engineer

CharterUP • Austin, TX

16h • Hybrid

About The Position

CharterUP is transforming the $450+ billion group transportation and mobility market with an AI native platform that powers modern charter, shuttle, and emerging autonomous vehicle operations. Trusted by many Fortune 500 companies, CharterUP connects enterprises, institutions, and event organizers to thousands of bus operators nationwide, while increasingly serving as the operating system for large scale shuttle and transit programs across airports, campuses, industrial sites, and major events. Through real time availability, transparent pricing, intelligent routing, and AI driven dispatch and optimization, CharterUP replaces a fragmented and opaque industry with automation, accountability, and scale. CharterUP is looking for a Principal Software Engineer with deep infrastructure experience to lead the deployment of AI across the enterprise, automating workflows and driving productivity at our growth-stage marketplace. You’ll build products that replace manual processes, collaborate cross-functionally to uncover high-impact opportunities, and ensure secure, scalable systems that keep pace with rapid growth.

Requirements

• 12+ years of hands-on experience designing and scaling infrastructure in fast-paced, high-growth environments
• Proven ability to identify inefficiencies and automate manual workflows using practical, AI-driven solutions
• Strong technical judgment with the ability to guide and debug complex systems across backend (Java) and frontend (Vue or React) stacks
• Deep understanding of cloud infrastructure, preferably AWS or GCP, and a passion for building reliable, scalable systems
• High ownership mindset with a track record of leading complex projects and delivering impactful tools across teams

Responsibilities

• Own and evolve core infrastructure systems while building AI-powered tools that automate workflows and boost productivity
• Leverage your infra expertise to guide AI-assisted development and rapidly ship reliable, scalable prototypes
• Collaborate across teams to identify operational inefficiencies and deliver automation that drives measurable impact
• Supervise AI-generated technical decisions, stepping in to debug complex issues as needed
• Set technical direction and champion best practices that integrate AI effectively into our engineering culture

Benefits

• Remote-First Flexibility: Work from anywhere we hire, with built-in flexibility. U.S.-based employees may reside in any of our 19 approved states.
• Comprehensive Health & Wellness: Medical, dental, and vision insurance, mental health support, virtual care, gym discounts, and family-building benefits. In the U.S., we cover 100% of premiums for employees. International benefits align with local standards.
• Time Off to Recharge: Paid time off so you can truly unplug. U.S.: 15 PTO days (increasing to 20 after 2 years) + 8 paid holidays. International policies vary by country.
• Financial Peace of Mind: Company-paid life, short-term, and long-term disability insurance where available.
• Performance-Driven Culture: Join a fast-moving, ambitious, and collaborative team that wins together.
• Referral Rewards: Earn bonuses for bringing top talent to the team.
• Planning for the Future: Long-term financial planning support. U.S.: 401(k) plan. International: region-specific savings programs where applicable.
• Top-Tier Tech: Choose a Mac or PC, plus monitor, keyboard, and mouse to hit the ground running.

What This Job Offers

• Job Type: Full-time
• Career Level: Principal
• Education Level: No Education Listed
• Number of Employees: 11-50 employees