VP Enterprise Sales

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: 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.

• Co