VP of Sales

This is a fully remote position, open to applicants in Vermont.

📋 Description

• Formulate and implement a comprehensive sales strategy that ensures predictable and scalable revenue growth across all targeted markets.

• Act as a true player-coach, providing active support to SEs on complex opportunities and personally managing our largest, most intricate enterprise deals to guarantee successful closures.

• Foster cross-functional collaboration among Marketing, Customer Success, and Product teams to ensure a cohesive GTM execution. Set shared KPIs, engage in joint planning, and maintain continuous feedback loops to enhance win rates, expansion, and product-market alignment.

• Construct and expand the sales organization from the ground up, including SEs, SDRs, and sales operations, while cultivating a culture of accountability, urgency, and performance excellence.

• Establish and uphold process discipline throughout the sales cycle, encompassing ICP clarity, outbound and SDR scripting, pipeline generation expectations, territory management, CRM hygiene, and thorough stage qualification.

• Create and oversee KPIs, forecasting models, and pipeline discipline to ensure consistent performance and clear revenue visibility.

• Take ownership of forecasting accuracy through meticulous pipeline inspections, predictable stage-progression criteria, and standardized qualification frameworks (MEDDPICC, SPICED, or similar). Collaborate with FP&A for dependable weekly, monthly, quarterly, and annual forecasts.

• Act as the public-facing sales leader for the organization by engaging in webinars, conferences, trade shows, and customer-oriented events, representing the unified CXT brand.

• Propel expansion in critical verticals (courier, shippers, healthcare) through targeted initiatives and strategic market development.

• Formulate and implement strategic partnership initiatives with key ecosystem players to unlock new revenue streams and enhance market position.

• Manage the complete sales process, from prospecting to negotiation and closure, ensuring operational excellence and an exceptional customer experience.

• Keep an eye on market trends, TMS competitive dynamics, and customer needs to sustain a strong, differentiated value proposition and guide ongoing GTM strategy.

• Exhibit leadership that fosters a high-accountability culture centered on transparency, coaching, data-driven decision-making, and continuous improvement.

⛳️ Requirements

• Over 15 years of progressive experience in B2B SaaS sales, including at least 10 years in senior sales leadership roles with direct responsibility for multi-million-dollar revenue targets.

• A minimum of 5 years of direct experience selling Transportation Management Systems (TMS) or last-mile/logistics technology is mandatory.

• Experience in scaling mid-market to enterprise SaaS companies is essential.

• Proven ability to achieve forecasting accuracy through thorough pipeline inspections, predictable stage-progression criteria, and standardized qualification frameworks (MEDDPICC, SPICED, or similar) for reliable weekly, monthly, quarterly, and annual reporting.

• Demonstrated capability in building and scaling sales organizations from the ground up using repeatable frameworks and playbooks.

🏝️ Benefits

• 100% Remote and Global: Enjoy the flexibility to live your best life from any location around the world.

• Flexible Work Environment: Work at your most productive times. We emphasize results and customer satisfaction over strict schedules.

• Dedicated Growth Path: Receive ongoing, meaningful feedback and support designed to help you reach your personal career aspirations.

• Access to Leading Tools and Technology: Enhance your capabilities with state-of-the-art tools, playbooks, and technology.

• Engaging Community Activities: Join in on coffee chats, happy hours, cooking classes, book clubs, and more!