Vice President, Sales

About Assail, Inc. Assail builds autonomous offensive AI that helps organizations prove what attackers can actually exploit. Serving enterprises, federal agencies, the Department of War, and the defense industrial base, Assail offers Ares for autonomous application and API security testing, and Reaper for continuous exploit validation in private cloud, on-premises, and disconnected environments.

• Boston, Massachusetts | Full-time | In office
• Assail builds autonomous offensive AI that helps organizations identify and
• validate security exposures before attackers exploit them. Our Ares platform
• tests APIs, web applications, mobile applications, and AI systems, helping
• security teams understand where they are vulnerable and prioritize action.
• We’re looking for a Vice President of Sales to lead our enterprise sales
• organization and build the foundation for sustained revenue growth. Reporting
• directly to Alissa Knight, CEO and Chief AI Officer, you will shape our sales
• strategy, develop our team, and work directly with customers on strategic
• opportunities.
• This role combines leadership with active selling. You will help move complex
• deals forward while establishing the processes, coaching, and forecasting
• discipline that allow the organization to grow. Your perspective will help
• inform how we position, package, and bring our technology to market.
• acquisition and expansion.
• representatives, with clear expectations and regular feedback.
• Build a repeatable sales process from qualification and discovery through
• proof of value, negotiation, procurement, and close.
• Participate directly in strategic opportunities, building relationships with
• security leaders, technical evaluators, and executive buyers.
• Establish reliable forecasting, useful pipeline reviews, and accurate CRM
• reporting.
• Partner with Marketing to develop qualified pipeline and improve customer
• targeting and messaging.
• customer evaluation plans and measurable success criteria.
• Work with Customer Success to support effective handoffs, renewals, and
• expansion.
• Partner with the CEO on sales planning, territories, hiring, pricing, and
• compensation.
• Bring customer feedback into product and business decisions.

• Experience leading enterprise cybersecurity or complex technical software
• sales, with demonstrated results against revenue goals.
• Experience building or improving sales processes in an early-stage or growing
• company.
• A record of coaching and developing sales professionals.
• Experience guiding opportunities through technical evaluations, enterprise
• procurement, and contract negotiations.
• The ability to translate technical capabilities into clear business value.
• Practical experience with forecasting, pipeline management, and CRM systems.
• A collaborative approach, openness to feedback, and willingness to adapt as
• you learn.
• Experience in application security, API security, exposure management,
• penetration testing, or AI security is helpful. You do not need experience in
• every one of these areas. No specific degree is required; we value relevant
• experience and demonstrated impact.
• Success means achieving revenue goals while building a sales organization that
• can sustain its results. We will look at qualified pipeline, forecast accuracy,
• conversion rates, sales efficiency, and team development, alongside the quality
• of your collaboration with customers and colleagues.
• We expect you to be comfortable using and administering the following tools
• Outreach (sales engagement)
• Nooks (AI-powered dialer and prospecting)
• A four-day workweek.
• strategy.
• The opportunity to build and develop a sales organization at a formative
• stage.
• Ongoing learning through close work with engineering, security specialists,
• and enterprise customers.
• If this opportunity interests you and your experience aligns with the core
• responsibilities, we encourage you to apply even if your background does not
• match every detail. We welcome different career paths and perspectives, and we
• value what you have learned and how you can contribute.

• Four-day workweek