VP of Sales

📋 Description

• Create and implement a detailed sales strategy that promotes consistent and scalable revenue growth across all target markets.

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

• Foster cross-functional collaboration among Marketing, Customer Success, and Product teams to guarantee cohesive GTM execution. Set shared KPIs, joint planning, and continuous feedback mechanisms to enhance win rates, expansion, and product-market fit.

• Build 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 maintain process discipline throughout the sales cycle, addressing ICP clarity, outbound and SDR scripting, pipeline generation expectations, territory management, CRM cleanliness, and thorough stage qualification.

• Define and oversee KPIs, forecasting models, and pipeline discipline to guarantee consistent performance and accurate revenue visibility.

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

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

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

• Develop and implement strategic partnership initiatives with key ecosystem players to unlock new revenue streams and bolster market positioning.

• Manage the entire sales process, from prospecting through negotiation to closing, ensuring operational excellence and an exceptional customer experience.

• Keep track of market trends, TMS competitive dynamics, and customer needs to uphold a strong, differentiated value proposition and inform ongoing GTM strategies.

• Exhibit leadership that promotes 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 in selling Transportation Management Systems (TMS) or last-mile/logistics technology is essential.

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

• A proven history of forecasting accuracy through rigorous pipeline evaluations, predictable stage-progression criteria, and standardized qualification frameworks (MEDDPICC, SPICED, or similar) for reliable reporting on a weekly, monthly, quarterly, and annual basis.

• Demonstrated ability to build and scale 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 anywhere in the world.

• Flexible Work Environment: Work during hours that best suit you. We value results and customer satisfaction over strict schedules.

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

• Access to Leading Tools and Technology: Enhance your skills with the latest tools, playbooks, and technologies available.

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