VP of Sales

About This Role

Lead and scale the sales organization for a leading Transportation Management System (TMS), driving predictable revenue growth and market leadership following a significant merger. This role involves developing comprehensive sales strategies, managing complex enterprise deals, and fostering a high-performance sales culture.

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 Sales Executives on complex opportunities and personally running point on largest, most complex enterprise deals to ensure successful close
• Drive cross-functional alignment across Marketing, Customer Success, and Product to ensure integrated go-to-market execution
• Build and scale the sales organization from the ground up, including Sales Executives, Sales Development Representatives, and sales operations
• Define and enforce process discipline across the sales cycle, including ideal customer profile clarity and pipeline generation expectations
• Establish and manage KPIs, forecasting models, and pipeline discipline to ensure consistent performance and accurate revenue visibility
• Own forecasting accuracy through rigorous pipeline inspection and standardized qualification frameworks (MEDDPICC, SPICED, or similar)
• 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

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

Skills

* Required skills

Benefits

Certifications