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Witness AI via Ashby

Regional Sales Director

Location not stated $84.5k–100k/yr head
still open verified 1d ago posted 6d ago seen 1h ago
Apply at jobs.ashbyhq.com

This is the employer's own posting, not a copy on a job board.

What we know

Is it still open?

Confirmed still open

Last checked 1d ago — checked against the employer's own applicant tracking system, which is the company answering directly.

We re-read the employer's own applicant tracking system and the posting was still there. That is the company answering directly.

Check this listing's status as JSON

How old is it?

Posted 6d ago

The date the source published, not the day we noticed it (2026-09-25). Last seen at its source 1h ago.

We have tracked this listing since 25 Sep 2026 (5 days). The employer's own board has carried it every time we have read it, most recently 1 hour ago.

Is it remote?

Remote

That is the location the employer filed this posting under. Quoted as written — we do not re-word the source's own location.

Who may apply?

Not stated

The description states no restriction of its own. This is the source's own tag.

Pay

$84.5k–100k/yr

Read out of the job description by us, not from a structured field. Shown in the posting's own currency and period; we never convert.

Skills named in the ad

CRMCold OutreachHubSpotMentoringNegotiationSalesforce

Recognised terms only, from a fixed vocabulary — this is what CV matching compares against.

Carried by 1 source

The listing

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.)

Apply at jobs.ashbyhq.com