Regional Sales Director
At a glance
Director-level Sales Leadership role at Witness AI. Remote, United States · full-time · $84,500–$100,000 base.
growthroles summary, based on the employer's posting.
What you'll do
- Run enterprise deals from initial prospecting and qualification through negotiation and closing
- Create territory plans for strategic enterprise accounts and deliver against quarterly and annual targets
- Build relationships with security, data science, and IT decision-makers
- Coordinate with marketing, SDRs, and sales engineering to create pipeline and demonstrate technical value
- Bring customer and market input into product direction while representing the company at industry events
What you bring
- At least seven years selling to enterprise customers, ideally in cybersecurity, AI/ML infrastructure, or SaaS
- A track record of closing deals worth six or seven figures with technical and business buyers
- Working knowledge of security architecture, cloud infrastructure, or AI/ML workflows
- You can explain complex technology clearly to engineers and executives while negotiating and presenting effectively
Who this fits
You’ll suit a hands-on sales leader who can operate independently while territory strategy and go-to-market processes are still taking shape. The role is based in Boston or the Northeast and reports to the VP of Sales. Experience selling to Fortune 1000, federal, or regulated-industry customers is a plus.
From the employer
Job Title: Regional Sales Director
Location: Boston/NE
Reports to: VP of Sales
About WitnessAI:
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.
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:
$84,500 - $100,000 (The exact salary will be determined based on the selected candidate’s location, qualifications, experience, and relevant skills.)
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