---
title: 'Regional Sales Director at Witness AI'
canonical: 'https://feeny.ai/job/regional-sales-director-witness-ai-remote-wsw9yt15fyy3'
type: 'job'
last_seen: '2026-10-18'
---

# Regional Sales Director at Witness AI

- **Company:** Witness AI
- **Location:** Remote
- **Employment:** full-time
- **Work type:** remote
- **Posted:** 2026-09-25
- **Last confirmed live:** 2026-10-18
- **Apply:** https://jobs.ashbyhq.com/witnessai/908af353-f58f-48f9-978f-f2e4e36e949e

## Job description

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.)

## About Witness AI

## Company Overview
- **One-liner**: WitnessAI provides a unified AI security and governance platform that helps enterprises observe, control, and protect all AI activity across employees, models, applications, and agents.
- **Entity Type**: Private (Venture-backed)
- **Headquarters**: Mountain View, California, United States
- **Founded**: 2023
- **Founders**: Rick Caccia (CEO), Jordan Blake (former CTO, left Apr 2026), Gil Spencer (former CTO, left Mar 2026), Roger Thornton (Co-Founder & Board Member)

## Core Business
- **Primary industry**: AI Security & Governance / Data Security Software Products
- **Target customers**: Enterprise IT security leaders, large organizations deploying AI across workforces (B2B, Enterprise)
- **Mission**: To make AI safe for the enterprise — enabling innovation without sacrificing security or control.

## Products & Services
- **WitnessAI Platform**: A unified, AI-native platform providing visibility, control, and runtime security for all AI interactions. Key capabilities include:
    - **Observe**: Shadow AI discovery, real-time inventory of AI apps, agents, and MCP servers; classify interactions by type and intent.
    - **Control**: Intelligent prompt routing, role/department-based policies, granular audit trails, real-time data redaction for compliance (PCI DSS 4.0.1), and enforcement across employees and AI agents.
    - **Protect**: Runtime security against prompt injections, jailbreaks, and data exfiltration; bidirectional content guardrails; automated AI red-teaming; protection for customer-facing AI interactions.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed
- **Key Metric**: **Total Funding**: $85.5M (across 3 rounds)
    - Venture Round (Jan 2026): $58.0M (5 investors)
    - Series A (May 2024): $27.5M (led by Google Ventures, Ballistic Ventures)
    - Non-Equity Assistance (Mar 2025): AWS & Crowdstrike Cybersecurity Accelerator
- **Notable Investors/Partners**: Google Ventures, Ballistic Ventures, Sound Ventures, Forgepoint Capital, Fin Capital, Qualcomm Ventures, Samsung Ventures, AWS, CrowdStrike
- **Growth Signals**: 
    - Headcount grew **92.5% YoY** (76 employees as of mid-2026)
    - Operates in 5 countries (US, India, Egypt, UK, Japan)
    - LinkedIn followers: 7,454 (up 138.3% YoY)
    - Recent integrations with F5 BIG-IP, support for Microsoft Copilot governance
    - Appointed retired U.S. Army General Paul M. Nakasone to the Board of Directors (Dec 2024)

## Competitive Advantages
- **AI-native architecture**: Built from the ground up for the AI era, not retrofitted on legacy security stacks — designed to evolve across ML, GenAI, and agentic AI.
- **Single-tenant, data-sovereign design**: Meets strict enterprise compliance needs (PCI DSS, data sovereignty) with granular audit trails and real-time data masking.
- **Agent-ready**: Governs both human employees and AI agents, tracing every agent action to a human identity, enforcing control over MCP servers and tools.
- **Network-level visibility + lightweight API deployment**: Offers deep visibility without heavy agent installation.
- **Strong leadership pedigree**: CEO Rick Caccia (Palo Alto Networks, Google, Symantec, ArcSight, Exabeam); team includes veterans from Palo Alto Networks (6), Zscaler (2), SentinelOne, Microsoft.

## Strategic Focus
- **Scale enterprise adoption**: Expanding platform capabilities to cover the full spectrum of AI usage (employees, agents, customer-facing apps).
- **Deepen compliance & regulatory readiness**: Meeting global regulations (PCI DSS, GDPR, etc.) and enabling safe AI usage in regulated industries.
- **Agentic AI governance**: Leading the shift to secure AI agents and autonomous workflows, with runtime controls for agent actions.
- **Global expansion**: Building presence in EMEA and APAC (UK, Japan) to serve multinational enterprises.

## Why Work Here
- **Remote-first, office-ready**: Work from anywhere in the U.S. with a home office stipend; Bay Area office available with weekly lunches and stocked kitchen.
- **Flexible PTO**: Take the time you need.
- **Comprehensive benefits**: Medical, dental, vision (HSA/FSA options), life & disability insurance, 401(k) with pre-tax/Roth options.
- **Culture**: Described as a mix of top-tier security talent (Palo Alto Networks, Zscaler, Exabeam alumni) building something foundational. Emphasis on "making AI safe for the enterprise" — a mission-driven environment.
- **Growth stage**: 76 employees with 92.5% YoY growth — early enough for impact, established enough with $85.5M funding for stability.
- **Engineering focus**: Strong technical team (26% of staff in technical roles), building a platform that spans security, AI, and data governance.

## Sources
1. [witness.ai](https://witness.ai/)
2. [witness.ai/about-us](https://witness.ai/about-us/)
3. [witness.ai/careers](https://witness.ai/careers/)
4. [jobs.ashbyhq.com/witnessai](https://jobs.ashbyhq.com/witnessai)
5. [linkedin.com/company/witnessai](https://www.linkedin.com/company/witnessai)

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