
Regional Sales Director
Required skills
- Enterprise Sales
- Cybersecurity
- AI/ML Infrastructure
- SaaS
- Technical Stakeholders
- Business Stakeholders
- Security Architectures
- Cloud Infrastructure
- AI/ML Workflows
- Technical Curiosity
Nice to have
- Cybersecurity Ecosystem
- AI Ecosystem
- Cloud Security Ecosystem
- SDRs
- AEs
- Salesforce
Role summary
WitnessAI, a fast-growing AI Security startup, seeks a Regional Sales Director to drive enterprise sales growth in the Boston/NE territory. This hands-on role involves owning the full sales cycle, developing territory plans, building relationships with security, AI, and IT leaders, and collaborating with marketing and engineering teams. The ideal candidate has 7+ years of enterprise sales experience, preferably in cybersecurity or AI/ML, a proven record of closing significant deals, and a deep understanding of relevant technologies. Experience in Fortune 1000 or regulated industries is a plus. The role offers a hybrid work environment, competitive compensation, and the opportunity to shape go-to-market strategy in a rapidly evolving market.
Job Title: Regional Sales Director
Reports to: VP of Sales
About WitnessAI:
WitnessAI is the unified AI security and governance platform enterprises trust to govern and protect all AI activity. We provide complete, network-level visibility into every interaction including employees and autonomous agents, even in native apps where legacy tools are blind.
Unlike security that relies on outdated keywords, our platform understands intent, enabling intelligent policies that stop novel threats like prompt injection while empowering productivity. WitnessAI transforms security from a bottleneck into the enabler of your AI strategy as the confidence layer for enterprise AI.
The Role
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.
What You’ll Do
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.
What We’re Looking For
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.
Nice to Have
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.
Why Join Us
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.
Benefits:
Hybrid work environment
Competitive salary, health, dental, and vision insurance
401(k) plan
Opportunities for professional development and growth
Generous vacation policy
Salary range:
$300,000 - $350,000 OTE (The exact salary will be determined based on the selected candidate’s location, qualifications, experience, and relevant skills.)
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