Senior Director of Sales (AI)

TL;DR

Senior Director of Sales (AI): Scale revenue from strategy to execution for an AI platform detecting retail theft in real time with an accent on building high-performing sales teams, closing enterprise deals, and expanding into new retail verticals. Focus on owning top-line targets, driving 75%+ YoY growth to $300M ARR, and turning customers into advocates through retention and expansion.

Location: Remote United States. Travel ready — minimum 3x per month to close deals, support the team, and build relationships.

Compensation: $130,000 - $180,000 base salary + uncapped commission (OTE 300K - 400k)

Company

AI platform helping 20,000+ retail stores detect and deter theft in real time, expanding from food service into grocery, c-stores, and broader retail.

What you will do

• Own top-line revenue targets and build scalable GTM strategy across enterprise and mid-market for AI software + hardware.
• Lead, coach, and hire sales reps, account managers, and SDRs while closing key 6-7 figure deals yourself.
• Strengthen distribution partnerships, expand into adjacent retail verticals, and drive customer success and expansion.
• Develop KPIs, forecasting, sales processes, and methodologies like Sandler or MEDDIC.
• Refine CRM, reporting, and incentive structures for pipeline visibility and team performance.

Requirements

• 8+ years in SaaS/technology sales, leading teams (ideally 10-20+ people).
• Proven track record scaling sales to $20M+ ARR with 75%+ YoY growth and closing 6-7 figure deals.
• Player-coach mentality — sell and lead simultaneously; travel 3x/month minimum.
• Immediate availability; creative deal-making in ambiguous environments.
• Motivational, competitive, opinionated about customer success; believer in equity.

Nice to have

• Experience in retail, foodservice, or distribution channels.
• Track record elevating customer success; EOS experience.
• "Best sales person" references.

Culture & Benefits

• Core values: Honest, Obsessive, Urgent, Systematic, Excellence; live EOS.
• Competitive base + aggressive commission + meaningful equity; health, dental, vision benefits.
• Flexible PTO and hybrid work options in a fast-scaling startup.

Hiring process

• Multiple interviews with Founder, C-Suite, and team.
• Working session on deals, process, and leadership style.
• References checking for "best sales person" feedback.