VP of Sales (OTE $300,000/year USD), @CXT Software

Are you a senior sales leader ready to build the next chapter of the largest Transportation Management System (TMS) in the market? This role offers a rare opportunity to help shape a newly unified sales organization following the merger of two industry leaders, with direct impact on revenue growth, go-to-market execution, and market leadership. CXT Software provides the technology backbone for delivery operations, serving courier, last-mile, and healthcare logistics companies across North America. Following the merger of CXT Software and e-Courier, we’ve brought together two established platforms to create the largest TMS purpose-built for last-mile and courier operations. This role sits at the ground floor of the newly formed organization, with the mandate to help build, scale, and professionalize the sales engine while continuing to innovate and expand through acquisition. If you are passionate about logistics technology, thrive in complex, fast-moving environments, and want to play a defining role in building a category-leading TMS platform, this is an opportunity to make a meaningful and lasting impact. Responsibilities *Develop and execute a comprehensive sales strategy that drives predictable, scalable revenue growth across all target markets. *Lead as a true player-coach, actively supporting SEs on complex opportunities and personally running point on our largest, most complex enterprise deals to ensure successful close. *Drive cross-functional alignment across Marketing, Customer Success, and Product to ensure integrated GTM execution. Establish shared KPIs, joint planning, and continuous feedback loops to improve win rates, expansion, and product-market fit. *Build and scale the sales organization from the ground up, including SEs, SDRs, and sales operations, fostering a culture of accountability, urgency, and performance excellence. *Define and enforce process discipline across the sales cycle, including ICP clarity, outbound and SDR scripting, pipeline generation expectations, territory management, CRM hygiene, and rigorous stage qualification. *Establish and manage KPIs, forecasting models, and pipeline discipline to ensure consistent performance and accurate revenue visibility. *Own forecasting accuracy through rigorous pipeline inspection, predictable stage-progression criteria, and standardized qualification frameworks (MEDDPICC, SPICED, or similar). Partner with FP&A for reliable weekly, monthly, quarterly, and annual forecasts. *Serve as the public-facing sales leader for the organization by participating 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 execute strategic partnership initiatives with key ecosystem players to unlock new revenue channels and strengthen market position. *Own the full sales process, from prospecting to negotiation to close, ensuring operational excellence and a world-class customer experience. *Monitor market trends, TMS competitive dynamics, and customer needs to maintain a strong, differentiated value proposition and inform ongoing GTM strategy. *Demonstrate leadership that drives a high-accountability culture focused on transparency, coaching, data-driven decision-making, and continuous improvement. Requirements *15+ years of progressive experience in B2B SaaS sales, including at least 10 years in senior sales leadership roles with direct ownership of multi-million-dollar revenue targets. *5+ years of direct experience selling Transportation Management Systems (TMS) or last-mile / logistics technology is required. *Background scaling mid-market to enterprise SaaS companies. *Proven track record of forecasting accuracy through rigorous pipeline inspection, predictable stage-progression criteria, and standardized qualification frameworks (MEDDPICC, SPICED, or similar) for reliable weekly, monthly, quarterly, and annual reporting. * Demonstrated experience building and scaling sales organizations from the ground up using repeatable frameworks and playbooks. Nice to have *Experience in healthcare delivery, or related operational B2B verticals. *Prior experience in integrating sales teams post-acquisition. *MBA or other relevant graduate degree. *Professional certifications such as Certified Sales Executive, Strategic Sales Management, or equivalent leadership/sales credentials are considered a plus. *Experience leading public-facing commercial activities (webinars, events, speaking engagements) *Experience building strategic partnerships in the logistics ecosystem. Benefits More than just perks, they're the essential components of a rewarding career at CXT Software. *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! Compensation Base: US$200,000 Variable: US$100,000 Total OTE: US$300,000 CXT Software is an equal opportunity employer committed to a diverse workforce. We're seeking agile, resourceful experts ready to leverage creative problem-solving and ingenuity to drive our growth. If you're ready to be a key player in our exciting future, apply now. Are you a senior sales leader ready to build the next chapter of the largest Transportation Management System (TMS) in the market? This role offers a rare opportunity to help shape a newly unified sales organization following the merger of two industry leaders, with direct impact on revenue growth, go-to-market execution, and market leadership. CXT Software provides the technology backbone for delivery operations, serving courier, last-mile, and healthcare logistics companies across North America. Following the merger of CXT Software and e-Courier, we’ve brought together two established platforms to create the largest TMS purpose-built for last-mile and courier operations. This role sits at the ground floor of the newly formed organization, with the mandate to help build, scale, and professionalize the sales engine while continuing to innovate and expand through acquisition. If you are passionate about logistics technology, thrive in complex, fast-moving environments, and want to play a defining role in building a category-leading TMS platform, this is an opportunity to make a meaningful and lasting impact. Responsibilities *Develop and execute a comprehensive sales strategy that drives predictable, scalable revenue growth across all target markets. *Lead as a true player-coach, actively supporting SEs on complex opportunities and personally running point on our largest, most complex enterprise deals to ensure successful close. *Drive cross-functional alignment across Marketing, Customer Success, and Product to ensure integrated GTM execution. Establish shared KPIs, joint planning, and continuous feedback loops to improve win rates, expansion, and product-market fit. *Build and scale the sales organization from the ground up, including SEs, SDRs, and sales operations, fostering a culture of accountability, urgency, and performance excellence. *Define and enforce process discipline across the sales cycle, including ICP clarity, outbound and SDR scripting, pipeline generation expectations, territory management, CRM hygiene, and rigorous stage qualification. *Establish and manage KPIs, forecasting models, and pipeline discipline to ensure consistent performance and accurate revenue visibility. *Own forecasting accuracy through rigorous pipeline inspection, predictable stage-progression criteria, and standardized qualification frameworks (MEDDPICC, SPICED, or similar). Partner with FP&A for reliable weekly, monthly, quarterly, and annual forecasts. *Serve as the public-facing sales leader for the organization by participating 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 execute strategic partnership initiatives with key ecosystem players to unlock new revenue channels and strengthen market position. *Own the full sales process, from prospecting to negotiation to close, ensuring operational excellence and a world-class customer experience. *Monitor market trends, TMS competitive dynamics, and customer needs to maintain a strong, differentiated value proposition and inform ongoing GTM strategy. *Demonstrate leadership that drives a high-accountability culture focused on transparency, coaching, data-driven decision-making, and continuous improvement. Requirements *15+ years of progressive experience in B2B SaaS sales, including at least 10 years in senior sales leadership roles with direct ownership of multi-million-dollar revenue targets. *5+ years of direct experience selling Transportation Management Systems (TMS) or last-mile / logistics technology is required. *Background scaling mid-market to enterprise SaaS companies. *Proven track record of forecasting accuracy through rigorous pipeline inspection, predictable stage-progression criteria, and standardized qualification frameworks (MEDDPICC, SPICED, or similar) for reliable weekly, monthly, quarterly, and annual reporting. * Demonstrated experience building and scaling sales organizations from the ground up using repeatable frameworks and playbooks. Nice to have *Experience in healthcare delivery, or related operational B2B verticals. *Prior experience in integrating sales teams post-acquisition. *MBA or other relevant graduate degree. *Professional certifications such as Certified Sales Executive, Strategic Sales Management, or equivalent leadership/sales credentials are considered a plus. *Experience leading public-facing commercial activities (webinars, events, speaking engagements) *Experience building strategic partnerships in the logistics ecosystem. Benefits More than just perks, they're the essential components of a rewarding career at CXT Software. *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! Compensation Base: US$200,000 Variable: US$100,000 Total OTE: US$300,000 CXT Software is an equal opportunity employer committed to a diverse workforce. We're seeking agile, resourceful experts ready to leverage creative problem-solving and ingenuity to drive our growth. If you're ready to be a key player in our exciting future, apply now. Are you a senior sales leader ready to build the next chapter of the largest Transportation Management System (TMS) in the market? This role offers a rare opportunity to help shape a newly unified sales organization following the merger of two industry leaders, with direct impact on revenue growth, go-to-market execution, and market leadership. CXT Software provides the technology backbone for delivery operations, serving courier, last-mile, and healthcare logistics companies across North America. Following the merger of CXT Software and e-Courier, we’ve brought together two established platforms to create the largest TMS purpose-built for last-mile and courier operations. This role sits at the ground floor of the newly formed organization, with the mandate to help build, scale, and professionalize the sales engine while continuing to innovate and expand through acquisition. If you are passionate about logistics technology, thrive in complex, fast-moving environments, and want to play a defining role in building a category-leading TMS platform, this is an opportunity to make a meaningful and lasting impact. Responsibilities *Develop and execute a comprehensive sales strategy that drives predictable, scalable revenue growth across all target markets. *Lead as a true player-coach, actively supporting SEs on complex opportunities and personally running point on our largest, most complex enterprise deals to ensure successful close. *Drive cross-functional alignment across Marketing, Customer Success, and Product to ensure integrated GTM execution. Establish shared KPIs, joint planning, and continuous feedback loops to improve win rates, expansion, and product-market fit. *Build and scale the sales organization from the ground up, including SEs, SDRs, and sales operations, fostering a culture of accountability, urgency, and performance excellence. *Define and enforce process discipline across the sales cycle, including ICP clarity, outbound and SDR scripting, pipeline generation expectations, territory management, CRM hygiene, and rigorous stage qualification. *Establish and manage KPIs, forecasting models, and pipeline discipline to ensure consistent performance and accurate revenue visibility. *Own forecasting accuracy through rigorous pipeline inspection, predictable stage-progression criteria, and standardized qualification frameworks (MEDDPICC, SPICED, or similar). Partner with FP&A for reliable weekly, monthly, quarterly, and annual forecasts. *Serve as the public-facing sales leader for the organization by participating 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 execute strategic partnership initiatives with key ecosystem players to unlock new revenue channels and strengthen market position. *Own the full sales process, from prospecting to negotiation to close, ensuring operational excellence and a world-class customer experience. *Monitor market trends, TMS competitive dynamics, and customer needs to maintain a strong, differentiated value proposition and inform ongoing GTM strategy. *Demonstrate leadership that drives a high-accountability culture focused on transparency, coaching, data-driven decision-making, and continuous improvement. Requirements *15+ years of progressive experience in B2B SaaS sales, including at least 10 years in senior sales leadership roles with direct ownership of multi-million-dollar revenue targets. *5+ years of direct experience selling Transportation Management Systems (TMS) or last-mile / logistics technology is required. *Background scaling mid-market to enterprise SaaS companies. *Proven track record of forecasting accuracy through rigorous pipeline inspection, predictable stage-progression criteria, and standardized qualification frameworks (MEDDPICC, SPICED, or similar) for reliable weekly, monthly, quarterly, and annual reporting. *Demonstrated experience building and scaling sales organizations from the ground up using repeatable frameworks and playbooks. Nice to have *Experience in healthcare delivery, or related operational B2B verticals. *Prior experience in integrating sales teams post-acquisition. *MBA or other relevant graduate degree. *Professional certifications such as Certified Sales Executive, Strategic Sales Management, or equivalent leadership/sales credentials are considered a plus. *Experience leading public-facing commercial activities (webinars, events, speaking engagements) *Experience building strategic partnerships in the logistics ecosystem. Benefits More than just perks, they're the essential components of a rewarding career at CXT Software. *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! Compensation Base: US$200,000 Variable: US$100,000 Total OTE: US$300,000 CXT Software is an equal opportunity employer committed to a diverse workforce. We're seeking agile, resourceful experts ready to leverage creative problem-solving and ingenuity to drive our growth. If you're ready to be a key player in our exciting future, apply now.