VP of Sales

📋 Description

• Create and implement a comprehensive sales strategy that fosters predictable and scalable revenue growth across all target markets.

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

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

• Build and expand the sales organization from the ground up, incorporating SEs, Sales Development Representatives (SDRs), and sales operations while cultivating a culture of accountability, urgency, and performance excellence.

• Define and uphold process discipline throughout the sales cycle, including clarity on Ideal Customer Profiles (ICP), outbound and SDR scripts, pipeline generation expectations, territory management, customer relationship management (CRM) hygiene, and rigorous stage qualification.

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

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

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

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

• Develop and implement strategic partnership initiatives with key ecosystem players to open new revenue channels and enhance market positioning.

• 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 Transportation Management Systems (TMS), and customer needs to sustain 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 at least 10 years in senior sales leadership positions holding 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.

• Proven success in achieving forecasting accuracy through meticulous 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 scaling sales organizations from the ground up utilizing repeatable frameworks and playbooks.

🏝️ Benefits

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

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

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

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

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