Vice President, Sales

Vice President of Sales Boston, Massachusetts | Full-time | In office

About Assail

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.

The opportunity

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.

What you’ll do

Own quarterly and annual recurring revenue targets across new customer acquisition and expansion.

Recruit, coach, and develop account executives and sales development 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.

Collaborate with Engineering and technical teams to define achievable 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.

What you’ll bring

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.

How we’ll measure success

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.

Tools you should know

We expect you to be comfortable using and administering the following tools:

• HubSpot (CRM)
• Outreach (sales engagement)
• Nooks (AI-powered dialer and prospecting)

What you can expect

A four-day workweek.

• Unlimited Paid Time Off

Direct collaboration with the CEO and a meaningful voice in commercial 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.

We welcome your application

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.

Assail is an equal opportunity employer. We are committed to a respectful, inclusive workplace and to providing reasonable accommodations during the hiring process.