Regional Sales Director

Location: Boston/NE
Reports to: VP of Sales

WitnessAI is a fast-growing, AI Security startup dedicated to enabling safe and effective AI use for enterprises. Our cutting-edge platform helps organizations innovate and enjoy the power of generative AI, without losing control, privacy, or security.

As a Regional Sales Director, you’ll be responsible for driving growth in your territory by identifying, engaging, and closing business with enterprise customers. You’ll work closely with marketing, solutions engineering, and product teams to deliver value-driven sales conversations and build deep relationships with security, AI, and IT leaders.

This is a hands-on, early-stage role where you’ll help shape our go-to-market motion, refine our sales playbook, and represent the company in a fast-evolving market category.

• Own the full sales cycle — from prospecting and qualification through negotiation and close.

• Develop and execute a territory plan focused on strategic enterprise accounts.

• Build relationships with key decision-makers in security, data science, and IT.

• Partner with marketing and SDRs to generate high-quality pipeline.

• Work with Sales Engineering to scope technical requirements and deliver compelling demos.

• Provide market and customer feedback to influence product direction and roadmap.

• Represent the company at events, conferences, and key industry forums.

• Consistently meet or exceed quarterly and annual sales targets.

• 7+ years of enterprise sales experience, preferably in cybersecurity, AI/ML infrastructure, or SaaS.

• Proven record of closing six- and seven-figure deals with technical and business stakeholders.

• Deep understanding of security architectures, cloud infrastructure, or AI/ML workflows.

• Strong technical curiosity — able to articulate complex technology to both engineers and executives.

• Experience selling into Fortune 1000, federal, or regulated industries (finance, healthcare, etc.) a plus.

• Self-starter mentality — thrives in early-stage environments with high autonomy and evolving GTM processes.

• Excellent communication, negotiation, and presentation skills.

• Network in the cybersecurity, AI, or cloud security ecosystem.

• Experience building or mentoring early GTM teams (SDRs, SEs, or AEs).

• Familiarity with CRM tools (Salesforce, HubSpot) and sales enablement platforms.

• Prior startup experience — you know how to build structure from zero.

• Build the foundation of our go-to-market strategy in a new and rapidly growing category.

• Represent a differentiated, high-impact product solving one of the biggest challenges in AI adoption.

• Competitive compensation and meaningful equity in a fast-scaling company.

• Collaborative, transparent, and mission-driven culture.

• Backing from world-class investors and advisors in AI, cybersecurity, and enterprise software.

• Hybrid work environment

• Competitive salary, health, dental, and vision insurance

• 401(k) plan

• Opportunities for professional development and growth

• Generous vacation policy