VP of Sales

📋 Description

• Create and implement a thorough sales strategy aimed at generating predictable and scalable revenue growth across all target markets.

• Act as a true player-coach, providing active support to Sales Engineers (SEs) on complex opportunities while personally leading our most significant and intricate enterprise deals to ensure successful closures.

• Foster cross-functional collaboration among Marketing, Customer Success, and Product teams to guarantee integrated go-to-market (GTM) execution. Set shared key performance indicators (KPIs), engage in joint planning, and maintain continuous feedback loops to enhance win rates, expansion, and product-market fit.

• Build and expand the sales organization from the ground up, including SEs, Sales Development Representatives (SDRs), and sales operations, while nurturing a culture centered on accountability, urgency, and performance excellence.

• Establish and uphold process discipline throughout the sales cycle, including clarity on ideal customer profiles (ICP), outbound and SDR scripting, pipeline generation expectations, territory management, CRM cleanliness, and rigorous stage qualification.

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

• Ensure forecasting accuracy through meticulous pipeline review, predictable stage-progression criteria, and standardized qualification frameworks (MEDDPICC, SPICED, or similar). Collaborate with Finance and Accounting (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-facing events, representing the cohesive CXT brand.

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

• Develop 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 to closure, ensuring operational excellence and a premier customer experience.

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

• Exhibit leadership that cultivates 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 at least 10 years in senior sales leadership positions that include 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 necessary.

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

• A proven history of forecasting accuracy through thorough pipeline inspection, 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 scaling sales organizations from the ground up utilizing repeatable frameworks and playbooks.

🏝️ Benefits

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

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

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

• Access to Leading Tools and Technology: Enhance your skills with the most up-to-date tools, playbooks, and technology.

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