VP of Sales

📋 Description

• Formulate and implement a comprehensive sales strategy aimed at achieving predictable and scalable revenue growth across all targeted markets.

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

• Foster cross-functional alignment among Marketing, Customer Success, and Product to ensure cohesive GTM execution. Establish shared KPIs, joint planning initiatives, and continuous feedback loops to enhance win rates, expansion, and product-market fit.

• Construct and scale the sales organization from the foundation up, incorporating SEs, SDRs, and sales operations while cultivating a culture of accountability, urgency, and performance excellence.

• Define and uphold process discipline throughout the sales cycle, which includes ICP clarity, outbound and SDR scripting, pipeline generation expectations, territory management, CRM hygiene, and rigorous stage qualification.

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

• Ensure forecasting accuracy through thorough 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.

• Serve as the public-facing sales leader for the organization by engaging in webinars, conferences, trade shows, and customer-facing events, representing 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 enhance market positioning.

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

• Track market trends, TMS competitive dynamics, and customer needs to maintain a strong, differentiated value proposition and inform ongoing GTM strategy.

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

⛳️ Requirements

• Over 15 years of progressive experience in B2B SaaS sales, with a minimum of 10 years in senior sales leadership roles responsible for multi-million-dollar revenue targets.

• At least 5 years of direct experience selling Transportation Management Systems (TMS) or last-mile/logistics technology is essential.

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

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

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

🏝️ Benefits

• 100% Remote and Global: Enjoy the freedom to live your best life from anywhere in the world.

• Flexible Work Environment: Work at times that suit you best. We prioritize results and customer satisfaction over rigid schedules.

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

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

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