[Remote] Director of Operations & Vendor Compliance

Note: The job is a remote job and is open to candidates in USA. CharterUP is transforming the group transportation and mobility market with an AI native platform. They are seeking a Director of Operations and Vendor Compliance to lead data-driven operational strategies, ensure compliance, and drive performance improvements across teams.

Responsibilities

• Own the compilation, analysis, and visualization of operational data building Tableau dashboards and reporting frameworks to identify opportunities, monitor KPIs, and support executive decision making
• Deliver actionable insights to executive leadership, ensuring data informs daily execution and long-term strategy
• Advanced ability to manipulate, clean, and interpret large datasets; experience with BI tools (Tableau, Looker, Power BI) and proficiency in SQL or other query languages strongly preferred. Must be able to build dashboards and explain analytical reasoning in detail
• Serve as the VP’s operational extension—taking tactical execution and operational oversight off their plate
• Drive cross-functional priorities with discipline, ensuring initiatives are executed with rigor and leadership bandwidth is preserved
• Lead a distributed team of managers and supply specialists, ensuring leaders under you are aligned, supported, and held accountable
• Set clear expectations, track performance, and consistently drive improvement against KPIs for productivity, efficiency, and SLA attainment
• Identify and execute strategies to improve operational efficiency and margin attainment, including new tools, automation, and process redesign
• Drive initiatives focused on reducing service failures and improving provider capacity through rigorous data analysis and continuous improvement
• Build region-specific margin strategies through cross-functional collaboration with Service Operations and Data Science
• Strengthen pricing integrity controls to ensure vendor pricing aligns with market standards and supports wholesale margins
• Provide senior leadership to the compliance function, ensuring vendor adherence to company policies, contractual obligations, and operational standards
• Oversee programs to strengthen delivery reliability and risk management

Skills

• 8+ years of experience leading operations in high-volume service delivery, dispatching or contact center environments ideally within transportation, mobility, or other complex service industries where compliance, customer satisfaction, and vendor management are critical
• Proven success managing frontline leaders and large teams in high-volume, high-stakes environments
• Advanced ability to compile, analyze, and visualize data using Tableau, Excel, and Google Sheets—capable of building dashboards and reporting independently without reliance on a dedicated analyst
• Strong track record of driving manager performance and holding teams accountable to KPIs
• Ability to balance strategic vision with tactical execution, rolling up sleeves when needed to solve problems, build processes, and drive results
• Vendor-facing communication and escalation management skills with executive presence
• Highly organized, data-driven, and comfortable making decisions under pressure while managing both short-term problem-solving and long-term process improvements
• Experience with BI tools (Tableau, Looker, Power BI) and proficiency in SQL or other query languages strongly preferred
• The ideal candidate will have worked in vendor management in a 2 sided marketplace

Benefits

• Flexible Work Model: CharterUP operates as a remote-first company, with select roles requiring regular, in-office presence based on team and business needs. Role-specific expectations will be shared during the hiring process. 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.
• 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.

Company Overview