VP of Sales

About This Role

This role will lead and scale the sales organization for a leading Transportation Management System (TMS) provider, driving revenue growth and market leadership following a significant merger. The Vice President of Sales will be responsible for developing and executing a comprehensive sales strategy, fostering a high-performance culture, and ensuring consistent achievement of revenue goals.

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
• Build and scale the sales organization from the ground up, including SEs, SDRs, and sales operations
• 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
• Serve as the public-facing sales leader for the organization by participating in webinars, conferences, trade shows, and customer-facing events
• 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
• 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
• Background scaling mid-market to enterprise SaaS companies

Qualifications

• 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

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
• Experience leading public-facing commercial activities (webinars, events, speaking engagements)
• Experience building strategic partnerships in the logistics ecosystem

Skills

* Required skills

Benefits