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Director, Inside Sales

United States
Remote 🌴
Apply Now
🔴 Closes on: 
May 9

About CharterUP

If you’ve been searching for a career with a company that values creativity, innovation, and teamwork, consider this your ticket to ride.

CharterUP is on a mission to shake up the fragmented $30 billion group ground transportation industry - with over 10,000 independent charter bus, minibus, and van operators across America. CharterUP is the first online marketplace that connects customers to a network of bus operators from coast to coast, currently holding over 600 operators on the network. Our revolutionary platform makes it possible to book a bus in just 60 seconds – eliminating the stress and hassle of coordinating group transportation for anyone from wedding parties to Fortune 500 companies. We’re introducing transparency, accountability, and accessibility to an industry as archaic as phone books. By delivering real-time availability and pricing, customers can use the CharterUP marketplace to easily compare quotes, vehicles, safety records, and reviews.

We're seeking team members who are revved up and ready to use technology to make a positive impact. As part of the CharterUP team, you'll work alongside some of the brightest minds in the technology and transportation industries. You'll help drive the future of group travel and help raise the bar for service standards in the industry, so customers can always ride with confidence.

But we're not just about getting from point A to point B – CharterUP is also committed to sustainability. By promoting group travel, we can significantly reduce carbon emissions and help steer our planet toward a greener future. In 2022 alone, we eliminated over 1 billion miles worth of carbon emissions with 25 million miles driven.

We’re a remote-first workplace, but we encourage collaboration and connection with hubs in Atlanta, GA and Austin, TX. CharterUP is looking for passionate and driven individuals to join our team and help steer us toward a better future for group transportation. On the heels of a $60 million Series A funding round, we’re ready to kick our growth into overdrive – and we want you to be part of the ride.

About The Role

The Director of Inside Sales is a pivotal role responsible for leading CharterUP's inside sales organization towards achieving and exceeding strategic objectives. This leadership position involves managing the entire ISR ecosystem, including direct oversight of ISR managers, to drive performance, exceed revenue goals, and enhance team effectiveness and NPS. The Director will work closely with the Chief Revenue Officer and other senior leadership to align sales strategies with company goals, ensuring a focus on both tactical day-to-day operations and long-term strategic initiatives.

Title: Director, Inside Sales

Reports to: CRO

Location: Remote

What You'll Do

Strategic Leadership:

  • Develop and implement sales strategies that align with CharterUP’s growth objectives.
  • Lead, mentor, and scale the inside sales organization, including ISR managers, to drive performance and achieve sales targets.
  • Collaborate with the CRO and senior leadership to refine sales processes, enhance sales training programs, and implement best practices across the sales team.

Drive Strategy With Data

  • Drive Strategy with Data:Utilize ISR performance data and industry insights to shape sales strategies. Champion AI-driven analytics for operational efficiency and decision-making.
  • Lead with a data-first approach to influence Inside sales direction and performance.

Operational Excellence

  • Drive effective shift coverage and ensure robust support mechanisms are in place for the ISR team, enhancing manager focus on key objectives like coaching and driving performance.
  • Optimize team structures and workflows to improve efficiency and effectiveness, facilitating large team sizes per manager.
  • Spearhead initiatives to streamline administrative tasks and reduce low-value activities among ISR Managers, enabling a focus on high-impact coaching and recognition.

Performance Management

  • Drive the team towards exceeding revenue goals through strategic direction and effective resource allocation.
  • Implement performance metrics and monitoring systems to track sales outcomes, providing actionable insights to continuously improve sales operations.
  • Foster a culture of excellence, recognition, and accountability, identifying and nurturing high performers while supporting the development of mid to low performers.

Innovation And Growth

  • Stay abreast of industry trends and technological advancements, leveraging insights to maintain CharterUP’s competitive edge.
  • Encourage innovation within the team, promoting initiatives that enhance customer experience and operational efficiency.
  • Guide the sales team in identifying and pursuing new business opportunities, expanding CharterUP's market presence.

What You'll Bring

  • Demonstrated success in driving Inside sales strategy and performance in a dynamic, high-growth startup setting with deep understanding of the sales process and dynamics.
  • Proven leadership in fast-paced, shift-based inside sales or inbound call center environments, with the ability to effectively manage and scale teams to exceed performance goals.
  • Experience in managing Managers or leading large teams of approximately 75+ Inside Sales individuals, including (SDRs), demonstrating the capability to scale sales efforts and maintain high performance in a structured environment.
  • Strong track record of exceeding revenue goals. This includes formulating operational strategies, developing training programs, and implementing systems that drive sales efficiency and effectiveness.
  • Demonstrated cross-functional leadership skills, showcasing the ability to collaborate with different departments to streamline processes and enhance overall sales productivity.
  • Proficient in utilizing and integrating a diverse technology stack, demonstrating the flexibility and technical acumen to leverage various tools and platforms to optimize sales performance and customer engagement.
  • Exceptional leadership skills, with the ability to inspire, mentor, and develop a high-performing sales team.
  • Strong strategic thinking and problem-solving abilities, capable of managing both day-to-day operations and long-term strategic initiatives.
  • Excellent communication and interpersonal skills, with the capability to collaborate effectively with all levels of management and staff.

Recruiting process

  • Step 1: Recruiting Interview
  • Step 2: Hiring Manager Interview
  • Step 3: Team Interview 
  • Step 4: Team Interview
  • Step 5: Presentation
  • Step 6: Hiring Manager Call
  • Offer & reference check
  • Welcome aboard! 


  • Base + OTE
  • Comprehensive benefits plan, including fully subsidized medical insurance for employees
  • 401(k) plan

CharterUP is an Equal Opportunity/Affirmative Action Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We make all employment decisions including hiring, evaluation, termination, promotional and training opportunities, without regard to race, religion, color, sex, age, national origin, ancestry, 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 the following states; Arizona, California, Colorado, Florida, Georgia, Hawaii, Missouri, North Carolina, New Hampshire, Nevada, New York, Oklahoma, South Dakota, Tennessee, Texas, Utah, Washington, and Wyoming.

Apply Now
🔴 Closes on: 
May 9
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