VP of Sales

📋 Description

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

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

• Facilitate cross-functional collaboration among Marketing, Customer Success, and Product teams to ensure a cohesive go-to-market execution. Establish shared KPIs, joint planning, and continuous feedback mechanisms to enhance win rates, expansion, and product-market alignment.

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

• Define and enforce process discipline throughout the sales cycle, covering ideal customer profile (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 reliable revenue visibility.

• Ensure forecasting accuracy through meticulous pipeline inspections, predictable stage-progression criteria, and standardized qualification frameworks (such as MEDDPICC, SPICED, or comparable). Collaborate with Financial Planning and Analysis (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.

• Drive 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 channels and strengthen market position.

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

• Monitor market trends, competitive dynamics in TMS, and customer needs to maintain a strong, differentiated value proposition and inform ongoing go-to-market 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 that involve direct ownership of 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 history of forecasting accuracy achieved through rigorous pipeline inspections, predictable stage-progression criteria, and standardized qualification frameworks (such as MEDDPICC, SPICED, or similar) for reliable weekly, monthly, quarterly, and annual reporting.

• Demonstrated experience in building and scaling 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 at your preferred times. 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 aspirations.

• 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!