CharterUP · 1 day ago

VP Enterprise Sales

United States

Contract

Remote

Director/Executive

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MarketplaceTransportation

Growth Opportunities

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Responsibilities

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 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.

Qualification

Find out how your skills align with this job's requirements. If anything seems off, you can easily click on the tags to select or unselect skills to reflect your actual expertise.

Revenue Growth StrategiesOutbound ProspectingComplex Sales ManagementAccount Management DesignOrganizational StructuringData Driven Decision MakingHolistic System ThinkingCharter Bus/Shuttle Industry KnowledgeAccountability Leadership

Required

Experience handling complexity in go-to-market motions, working across different verticals and segments with large deals.

Experience working with complex, large-scale deals with longer sales cycles (6 months to 2 years).

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).

Expertise in designing and managing an effective account management function, including determining the right handoff process between hunters and farmers.

Ability to structure the sales organization to balance hunting and farming, with a focus on maximizing productivity and minimizing friction.

Structured problem solver that relies on data to understand issues and make critical decisions.

Strong process orientation and ability to implement a structured sales methodology to improve forecasting and accountability.

Demonstrated success in driving and holding sales teams accountable and driving high performance.

Ability to think holistically about the organizational system, considering challenging trade-offs in design, including incentives and motivation.