VP of Sales

📋 Description

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

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

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

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

• Define and uphold process discipline throughout the sales cycle, covering ideal customer profile (ICP) clarity, outbound and SDR scripting, pipeline generation expectations, territory management, CRM hygiene, and stringent stage qualification.

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

• Ensure forecasting accuracy through meticulous pipeline inspections, 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.

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

• Drive growth in key verticals such as courier services, shippers, and healthcare through targeted initiatives and strategic market development.

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

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

• Keep abreast of market trends, competitive dynamics in TMS, 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 is essential.

• Background in scaling mid-market to enterprise SaaS organizations.

• 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 dependable 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 times that best suit you. We emphasize results and customer satisfaction over strict schedules.

• Dedicated Growth Path: Benefit from consistent, meaningful feedback and support designed to help you reach your personal career aspirations.

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

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