Aimed at experienced enterprise sales professionals with technical acumen who thrive in early-stage environments and can work remotely across the United States.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Witness AI via Ashby
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Unlike security that relies on outdated keywords, our platform understands intent, enabling intelligent policies that stop novel threats like prompt injection while empowering productivity.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.)
Source: Witness AI careers (Ashby)