VP of Sales

📋 Description

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

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

• Foster cross-functional collaboration among Marketing, Customer Success, and Product teams to ensure cohesive go-to-market (GTM) execution. Set shared KPIs, engage in joint planning, and maintain continuous feedback loops 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 maintain process discipline throughout the sales cycle, including clarity on Ideal Customer Profile (ICP), outbound and SDR scripts, pipeline generation expectations, territory management, CRM cleanliness, and rigorous stage qualification.

• Establish and oversee KPIs, forecasting models, and pipeline discipline to guarantee 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 Financial Planning & Analysis (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 targeted initiatives and strategic market development efforts.

• Develop and implement strategic partnership initiatives with key ecosystem players to unlock new revenue streams and bolster market position.

• Oversee the entire sales process, from prospecting to negotiation to closure, ensuring operational excellence and a top-tier customer experience.

• Keep abreast of market trends, TMS competitive dynamics, and customer needs to maintain a strong, differentiated value proposition and inform ongoing GTM strategies.

• Exhibit leadership that fosters a high-accountability culture focused on transparency, coaching, data-driven decision-making, and ongoing improvement.

⛳️ Requirements

• Over 15 years of progressive experience in B2B SaaS sales, with a minimum of 10 years in senior sales leadership roles having 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 in scaling mid-market to enterprise SaaS companies.

• Proven ability to maintain forecasting accuracy through rigorous pipeline inspections, predictable stage-progression criteria, and standardized qualification frameworks (such as MEDDPICC, SPICED, or similar) for reliable reporting on a weekly, monthly, quarterly, and annual basis.

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

🏝️ Benefits

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

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

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

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

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