Director, Enterprise Service Delivery

CharterUp, LLC.; Town of Texas (WI); Remote; USD 130,000 - 150,000; Full time

Job summary

CharterUP is searching for a strategic leader to oversee the Director of Enterprise Service Delivery role. This position is crucial for managing complex shuttle and event programs, ensuring operational excellence, and maintaining high customer satisfaction. The ideal candidate will thrive in fast-paced environments, lead a distributed team, and possess strong communication skills for client interaction.

Benefits

Remote Flexibility

Full Health & Wellness Coverage

15 days PTO

Company-provided life insurance

401(k) retirement plan

Tech Setup with preferred hardware

Qualifications

• 8+ years of experience in operations, service delivery, logistics, or client success.
• Strong client-facing communication and escalation management skills.
• Ability to handle ambiguity and make decisions under pressure.

Responsibilities

• Lead the day-to-day operations of enterprise service delivery team.
• Serve as main escalation point for high-value enterprise clients.
• Drive performance management by holding team accountable to KPIs.

Skills

Operations Management

Client Success Management

Logistics

Team Leadership

Communication

Job description

About CharterUP. CharterUP is transforming the $30 billion group transportation industry with cutting-edge technology and innovative SaaS software, delivering an industry-leading experience for both customers and operators. Trusted by most Fortune 500 companies, our platform connects users to thousands of charter bus and minibus operators nationwide. In just 60 seconds, customers can access real-time availability, transparent pricing, and detailed vehicle options—whether organizing a corporate event, a company shuttle, or a wedding. By streamlining what was once a fragmented and stressful process, CharterUP brings transparency, accountability, and efficiency to an industry overdue for innovation

With CharterUP, group transportation is no longer a hassle but an elevated, reliable experience. Join us as we lead the future of group travel.

Why Join Us

• Innovative Impact: Be part of the team that's revolutionizing group travel, setting new standards in an industry overdue for change.
• Growth Opportunities: As a hyper growth company and one of the fastest-growing companies recognized by Inc., there’s no better time to join our dynamic, growth-stage organization.
• Driven Team: Collaborate with some of the most driven minds in tech, all while working in a remote-first environment with a tech hub in Austin, TX.
• Funding and Stability: Our $60 million Series A funding was just the start—we’re poised for even greater expansion, and you can be part of this exciting journey. CharterUp has achieved this growth profitability and efficiently, ensuring long-term stability.

About the Role

Title: Director of Enterprise Service Delivery

Reports to: VP of Strategy

Location: Remote

CharterUP is seeking a strategic, operations-minded leader to serve as our Director of Enterprise Service Delivery—a critical position overseeing the execution and performance of our largest and most complex shuttle and event programs. Reporting directly to the VP of Enterprise Operations, this Director will lead the day-to-day operations across CharterUP’s enterprise transportation portfolio, managing a distributed team and ensuring operational excellence, team performance, and high customer satisfaction.

This leader will function as the escalation point for top-tier accounts and play a hands-on role in shaping delivery standards, improving team capability, and driving accountability across the function. The ideal candidate thrives in complex, fast-moving environments and knows how to balance executive client management with team leadership and operational rigor.

What You’ll Do

• Lead the day-to-day operations of CharterUP’s enterprise service delivery team, including Account Coordinators (ACs), Onsite Coordinators (OCs), and their managers.
• Serve as the primary escalation point for high-value enterprise clients when critical issues arise (e.g., Meta, construction clients, event partners).
• Ensure consistent execution of SOPs, SLAs, and compliance standards across all enterprise programs, including client-facing shuttle and event services.
• Drive performance management by holding team members accountable to KPIs, service standards, and response times.
• Coach and develop frontline managers and ICs, fostering a culture of accountability, urgency, and ownership.
  Collaborate closely with cross-functional teams (sales, finance, legal, and tech) to improve workflows and strengthen enterprise client experience.
• Build and maintain strong relationships with enterprise clients, demonstrating executive presence and a proactive problem-solving mindset.
• Identify and solve operational bottlenecks, vendor performance issues, and customer service risks.
• Partner with leadership on strategic growth planning, organizational design, and new account onboarding.

What You’ll Bring

• 8+ years of experience in operations, service delivery, logistics, or client success—ideally within transportation, freight, events, or field service environments.
• Proven success managing large teams and frontline leaders in high-volume, high-stakes environments.
• Strong client-facing communication and escalation management skills; executive presence is a must.
• Ability to handle ambiguity, make decisions under pressure, and balance short-term problem-solving with long-term process improvements.
• Experience overseeing compliance-heavy contracts and coordinating with third-party vendors.
• Highly organized, with a data-driven approach to managing team performance and program health.
• Comfort working across time zones, with occasional travel to high-profile client locations as needed.
• Step 1 - Video call: Talent Acquisition interview
• Step 4 - Video call: Team Interview
• Step 5 - Offer & reference check
• Welcome aboard!

Compensation:

$130,000 - $150,000 USD

Benefits & PerksWe take care of our team so you can focus on doing your best work. At CharterUP, you'll get:

• Remote Flexibility – Work from any of our 19 live/work states, with role-dependent exceptions
• Full Health & Wellness Coverage – 100% of premiums paid for medical, dental, and vision plans for employees - including mental health resources, Teledoc, gym discounts, and family planning benefits
• Time to Recharge – 15 days PTO (increases to 20 after 2yrs) + 8 paid holidays so you can actually unplug
• Financial Security – Company-provided life insurance, as well as short-term and long-term disability for employees who qualify
• Winning Culture – Join a high-performing, fast-paced, and supportive team that wins together
• Referral Bonuses – Get rewarded for bringing top talent to the team
• Future Planning – 401(k) retirement plan to help you invest in what’s next
• Tech Setup – Your choice of Mac or PC laptop, plus monitor, keyboard, and mouse.

CharterUP is an Equal Opportunity/Affirmative Action Employer. We make all employment decisions including hiring, evaluation, termination, promotional and training opportunities, without regard to race, religion, color, sex, age, national origin, ancestry, veteran status, sexual orientation, physical handicap, mental disability, medical condition, disability, gender or identity or expression, pregnancy or pregnancy-related condition, marital status, height and/or weight.

CharterUP candidates and employees must reside in any of the following states; Arizona, California, Colorado, Florida, Georgia, Hawaii, Mississippi, Missouri, North Carolina, New Hampshire, Nevada, New York, Oklahoma, South Dakota, Tennessee, Texas, Utah, Washington, and Wyoming.

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