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

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
• Own 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
• Partner with FP&A for reliable 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

• 100% Remote and Global
• Flexible Work Environment
• Dedicated Growth Path
• Access to Leading Tools and Technology
• Engaging Community Activities

Pay

US$200,000 Base

Schedule

Remote