Regional Sales Manager - Chicago

Must be located in the Chicago region

Accelerate Your Career in Cybersecurity

Join Pentera and take your career to the next level in cybersecurity. As a leader in Automated Security Validation, we help businesses around the world safely emulate real-world attacks to uncover their vulnerabilities—just like the world’s best red teams. At Pentera, you’ll be at the forefront of cybersecurity innovation, working on advanced tools that challenge organizations' defenses and push the limits of security testing.

With over 350 team members and 1,000 customers in more than 50 countries, Pentera is a growing company supported by top investors like Insight Partners, K1, and The Blackstone Group.

If you're looking to grow your skills, make a difference, and be part of an innovative team, Pentera is the place for you.

About the Role

We are looking for a highly motivated, self-driven, and experienced Regional Sales Manager specializing in enterprise sales, based in the Chicago territory. The ideal candidate is passionate about helping organizations defend against the world’s most advanced attackers and thrives in a high-velocity sales environment.

You’ll work closely with SDRs, ISRs, and channel partners to drive regional growth. You should bring a strong network of executive-level contacts, be adaptable to change, and have a proven ability to deliver results. We’re looking for someone who is customer-focused, driven, and ready to attack the market with energy and precision.

Roles and Responsibilities

• Identify, develop, and execute an enterprise account strategy to close new business opportunities and expand revenue across the assigned region.
• Scope, negotiate, and close agreements to meet or exceed booking and revenue quota targets.
• Access and build relationships with key decision-makers in enterprise accounts.
• Lead demos and complex pilots as a hands-on, customer-facing professional.
• Collaborate with end customers and channel partners to generate and close enterprise sales opportunities.
• Act as a strategic influencer with resellers and distributors to drive pipeline and deal flow.
• Take full ownership of sales forecasting, pipeline management, and reporting to regional leadership.

• Direct quota carrier with 3 years of experience in enterprise cybersecurity sales, with a track record of exceeding targets.
• Strong results orientation with expertise in forecasting, pipeline management, and discipline around sales metrics.
• Consultative sales skills with the ability to present Pentera’s technology and align it to both business and technical outcomes.
• Proven relationship in the region with decision makers like CIO, CTO, CFO, CISO
• Proven ability to build and manage relationships with senior executives.
• Experience working in and managing a CRM-based pipeline and forecast.
• Bachelor’s or Master’s Degree, or equivalent education and experience.
• Excellent communication, presentation, and negotiation skills.
• Self-starter with strong individual accountability and team collaboration mindset.
• Competitive, driven, and motivated by success in complex enterprise sales.
• Willingness to travel up to 50% as needed across the Eastern Canada region.
• Creative and adaptable in navigating enterprise sales challenges.
• A growth mindset and openness to feedback and learning.
• Experience in launching or scaling a new enterprise-level solution is a plus.

We are an equal opportunity employer and we are committed to building a diverse and talented workforce. We do not discriminate based on race, sex, religion, color, national origin, gender, gender identity, sexual orientation, age, marital status, veteran status, medical condition, disability, or any other class or characteristic protected by applicable law. We welcome candidates from all backgrounds to join us!