VP of Sales

📋 Description

• Design and implement a comprehensive sales strategy aimed at fostering predictable and scalable revenue growth across all target markets.

• Lead as an effective player-coach, providing active support to Sales Engineers (SEs) on complex opportunities while personally managing our largest and most intricate enterprise deals to ensure successful closures.

• Facilitate cross-departmental alignment across Marketing, Customer Success, and Product to guarantee cohesive go-to-market (GTM) execution. Establish shared KPIs, collaborative planning, and ongoing feedback loops to enhance win rates, expansion efforts, and product-market fit.

• 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 high performance.

• Define and uphold process discipline throughout the sales cycle, covering aspects such as Ideal Customer Profile (ICP) clarity, outbound and SDR scripting, pipeline generation expectations, territory management, CRM hygiene, and thorough stage qualification.

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

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

• Act as the public-facing sales leader for the organization by participating in webinars, conferences, trade shows, and customer-facing events, thus 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 open new revenue streams and enhance market positioning.

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

• Keep abreast of 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 centered on transparency, coaching, data-driven decision-making, and continuous improvement.

⛳️ Requirements

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

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

• Proven background in scaling mid-market to enterprise SaaS companies.

• Demonstrated track record of forecasting accuracy through meticulous pipeline inspection, predictable stage-progression criteria, and standardized qualification frameworks (such as MEDDPICC, SPICED, or similar) for dependable weekly, monthly, quarterly, and annual reporting.

• Proven experience in building and scaling 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!