Regional Sales Director (AI)

TL;DR

Regional Sales Director (AI): Building and leading a high-performing sales team to execute GTM motion for an agentic AI automation platform with an accent on scaling AE teams and driving revenue growth. Focus on designing repeatable sales playbooks, coaching multi-stakeholder technical deals, and evolving from first-line to second-line leadership.

Location: Must be based in or be able to work from the San Francisco or New York office

Compensation: On-Target Earnings $350K + Equity and Commission

Company

AI-native automation platform transforming enterprise operations by building intelligent agents that execute real-world workflows end-to-end.

What you will do

• Build, hire, and scale the AE team from the ground up, defining structure, territories, and hiring profiles.
• Coach the team through deal strategy, pipeline reviews, and forecast management.
• Develop and refine the sales playbook, including outbound motions, qualification frameworks, and demo narratives.
• Maintain a strategic book of business and close key deals to model best practices.
• Partner with GTM leadership to define ICP, pricing, and packaging.
• Collaborate cross-functionally with product and engineering to shape roadmap priorities based on customer feedback.

Requirements

• 5–8+ years of B2B SaaS sales experience.
• 2+ years of experience managing and developing high-performing AE teams.
• Proven track record of building and scaling sales teams at early- to growth-stage companies (Seed to Series C+).
• Deep understanding of full-cycle sales in technical or workflow automation solutions for IT, Security, or Engineering buyers.
• Based in or willing to work from the San Francisco or New York office.

Nice to have

• Experience scaling AE teams from 0 to 5+ reps in the mid-market segment.
• Familiarity with sales methodologies like MEDDIC, MEDDPICC, or Challenger.
• Comfort coaching technical demos and discussing APIs or automation platforms.
• Track record of promoting team members and building internal career paths.

Culture & Benefits

• Comprehensive health coverage and flexible PTO.
• Daily lunches, snacks, and onsite gym access.
• Regular team events and offsites.
• Meaningful early-stage equity.
• Culture valuing innovation, ownership, and accountability.