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VP Enterprise Sales

Remote, US

About CharterUP

CharterUP is transforming the $30 billion group transportation industry with cutting-edge technology, trusted by most Fortune 500 companies. By connecting customers to thousands of charter bus, minibus, and van operators nationwide, our platform elevates group travel, turning a traditionally fragmented and stressful process into a seamless experience. In just 60 seconds, users can access real-time availability, transparent pricing, and detailed vehicle options—whether they’re organizing a corporate event, a company shuttle, or a wedding. Our technology-driven approach 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: 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! 
Compensation
  • Comprehensive benefits plan, including fully subsidized medical insurance for employees
  • 401(k) plan

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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