VP of Sales

📋 Description

• Develop and implement a thorough sales strategy that fosters predictable, scalable revenue growth across all target markets.

• Act as a true player-coach by actively assisting Sales Engineers (SEs) on complex opportunities and taking the lead on our largest, most intricate enterprise deals to ensure successful closures.

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

• Construct and expand the sales organization from the ground up, which includes SEs, Sales Development Representatives (SDRs), and sales operations, while promoting a culture of accountability, urgency, and performance excellence.

• Define and enforce disciplined processes throughout the sales cycle, including Ideal Customer Profile (ICP) clarity, outbound and SDR scripting, pipeline generation expectations, territory management, CRM maintenance, and thorough stage qualification.

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

• Maintain forecasting accuracy through meticulous pipeline inspections, predictable stage-progression criteria, and standardized qualification frameworks (such as MEDDPICC, SPICED, or similar). Collaborate with Financial Planning & Analysis (FP&A) for reliable weekly, monthly, quarterly, and annual forecasts.

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

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

• Create and execute strategic partnership initiatives with key ecosystem players to unlock new revenue streams and reinforce market position.

• Oversee the entire sales process, from prospecting to negotiation to closing, ensuring operational excellence and delivering a world-class customer experience.

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

• 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, with a minimum of 10 years in senior sales leadership roles holding direct responsibility 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 scaling mid-market to enterprise SaaS companies is required.

• Proven history of forecasting accuracy through rigorous pipeline inspections, predictable stage-progression criteria, and standardized qualification frameworks (such as MEDDPICC, SPICED, or similar) for dependable weekly, monthly, quarterly, and annual reporting.

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

🏝️ Benefits

• 100% Remote and Global: Enjoy the freedom to live your best life from any location worldwide.

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

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

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

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