Vice President, Sales

Assail, Inc. • Boston, MA

14h • Onsite

About The Position

Assail is seeking a Vice President of Sales to lead its enterprise sales organization and build a foundation for sustained revenue growth. Reporting directly to the CEO and Chief AI Officer, this role will shape sales strategy, develop the team, and work with customers on strategic opportunities. It combines leadership with active selling: advancing complex deals while establishing the processes, coaching, and forecasting discipline needed to grow. The role will also inform how Assail positions, packages, and brings its autonomous offensive AI security platform to market.

Requirements

• 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.
• 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 while learning.

Nice To Haves

• Experience in application security, API security, exposure management, penetration testing, or AI security.

Responsibilities

• Own quarterly and annual recurring revenue targets across new customer acquisition and expansion.
• Recruit, coach, and develop account executives and sales development representatives, setting clear expectations and providing regular feedback.
• Build a repeatable sales process covering qualification, discovery, proof of value, negotiation, procurement, and close.
• Participate directly in strategic opportunities and build 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.
• Collaborate with Engineering and technical teams to define achievable customer evaluation plans and measurable success criteria.
• Work with Customer Success on 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.

Benefits

• Four-day workweek.
• Direct collaboration with the CEO and a meaningful voice in commercial strategy.
• Opportunity to build and develop a sales organization at a formative stage.
• Ongoing learning through close work with engineering, security specialists, and enterprise customers.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed