Vice President, Enterprise Sales

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

Title: Vice President, Enterprise Sales

Reports to: CRO

Location: Remote, Austin or Bay Area desirable

The VP of Enterprise Sales at CharterUP will be responsible for driving significant revenue growth by building and implementing a comprehensive outbound prospecting motion targeting key verticals such as construction, traditional shuttle industries (e.g., university shuttles), and events. This role requires a hands-on leader with expertise in managing complex, large-scale deals with long sales cycles, and the ability to design and manage an effective account management function. The ideal candidate will have experience structuring sales organizations to hunt and farm and will drive accountability for achieving activity metrics and the ultimate sales targets. Familiarity with the charter bus/shuttle industry is preferred but not required. This role offers the opportunity to build and scale a high-growth, complex enterprise sales business, contributing to CharterUP's goal of reaching $100 million in gross revenue next year in this division

What You'll Do

Revenue Growth

• Provide Hands-On Leadership: Ensure you are hands-on and willing to get involved in deals while also capable of structuring the organization for future growth. Develop growth strategies with the executive team and establish both short-term results and long-term revenue forecasting.
• Achieve/Exceed Revenue Targets: Own new revenue targets and develop a plan to achieve them.
• Develop Outbound Sales Strategies: Design and implement comprehensive outbound prospecting motions targeting enterprise charter, shuttle, and event verticals. Build and manage a robust outbound sales machine, including hiring and managing SDRs, ensuring accountability for prospecting across the organization.
• Manage Complex Sales Cycles: Oversee complex sales cycles, including RFP processes that span 12-18 months and sales cycles that can take 2-3 years. Scale the sales organization to handle larger, complex deals, and ensure team selling for significant contracts.
• Establish Account Management Functions: Create a formalized account management function to maximize value from existing clients and manage the transition from AE to account manager. Expand into new verticals such as government and events, which require different sales motions and strategies.
  
  

Organizational Alignment & Sales Management

• Organizational Structuring: Structure the sales organization to maximize productivity by clearly defining roles for outbound and inbound teams and how they support account managers.
• Segmentation Design: Design segmented organizations, creating distinct hunting, farming, and customer success teams, and determine the right time to transition accounts between these teams.
• Holistic System Thinking: Think holistically about the organizational system, considering challenging trade-offs in design, including incentives and motivation.
• Complexity Management: Handle complexity and resolve friction between sales teams, ensuring there is no overlap or double-crossing between channels and accounts.
• Events Vertical: Develop and execute a strategy to penetrate the events vertical, a previously untapped market for shuttle services.
• Market Research: Conduct market research to identify potential event organizers and planners.
• Solution Development: Develop customized solutions and packages for event transportation needs.
  

What You'll Bring

• GTM Motion Complexity: Experience handling complexity in go-to-market motions, working across different verticals and segments with large deals.
• Complex Sales Management: Experience working with complex, large-scale deals with longer sales cycles (6 months to 2 years).
• Outbound Prospecting Expertise: Experience in building and implementing a comprehensive outbound prospecting motion, particularly targeting industries such as construction companies, traditional shuttle industries (e.g., university shuttles), the government sector, and the events sector (e.g., large organizations and destination management companies handling major events).
• Account Management Design: Expertise in designing and managing an effective account management function, including determining the right handoff process between hunters and farmers.
• Organizational Structuring: Ability to structure the sales organization to balance hunting and farming, with a focus on maximizing productivity and minimizing friction.
• Data Driven: Structured problem solver that relies on data to understand issues and make critical decision
• Process Orientation: Strong process orientation and ability to implement a structured sales methodology to improve forecasting and accountability.
• Accountability Leadership: Demonstrated success in driving and holding sales teams accountable and driving high performance..
• Holistic System Thinking: Ability to think holistically about the organizational system, considering challenging trade-offs in design, including incentives and motivation. Nice to Have
• Charter Bus/Shuttle Industry Knowledge: Familiarity with the charter bus/shuttle industry is preferred but not a strict requirement.
  

Recruiting process

• Initial Step: Interview with the Head of Recruiting
• Step 1: Hiring Manager Interview
• Step 2 :Team Interview
• Step 3: Team Interview
• Step 4: Final Interview
• Step 5: Presentation
• Offer & reference check
• Welcome aboard!
• Be sure to use 14 pt font and preview before posting to confirm that the formatting is uniform
  
  

Compensation

• 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, Mississippi, Missouri, North Carolina, New Hampshire, Nevada, New York, Oklahoma, South Dakota, Tennessee, Texas, Utah, Washington, and Wyoming.