Top Tech Jobs & Startup Jobs in Chicago, IL

Leads enterprise sales across the Western United States, driving revenue growth, customer expansion, new business development, forecasting, and quota achievement. Manages, hires, trains, and motivates Account Executives; develops regional sales strategies, campaigns, channel partnerships, and upsell programs. Supports complex customer engagements, communicates technical and business value, provides market feedback, and influences product positioning. Requires cybersecurity vendor experience, executive-level relationship skills, and at least 50% travel.

Generates qualified sales opportunities through outbound phone, email, and social prospecting. The SDR engages target accounts, follows up on marketing leads, communicates Pentera’s cybersecurity value proposition, records activity in Salesforce, develops business relationships, and qualifies prospects for field sales. The role requires strong communication, organization, resilience, and collaboration with sales teams to optimize territory strategies. It offers a defined path toward closing sales roles.

Own the full enterprise sales cycle across the Pacific Northwest, including prospecting, discovery, demonstrations, proof-of-concepts, negotiation, and closing. Build a self-sourced pipeline, sell cybersecurity outcomes to CISOs and security leaders, use AI-assisted sales tools, maintain accurate forecasts, and provide customer insights to Product, Marketing, and sales leadership.

Manage and improve customer renewal processes for the Americas, overseeing high-volume renewals, negotiations with channel partners and end users, account priorities, forecasting, and renewal performance reporting. Collaborate with sales, customer success, finance, and product teams to drive retention and customer satisfaction. Analyze renewal trends, identify risks and opportunities, manage contracts, and engage C-level stakeholders while developing scalable renewal playbooks.

Own the full enterprise sales cycle, from prospecting and discovery through demonstrations, proof-of-concepts, negotiation, and close. Build and self-source pipeline, sell cybersecurity solutions to CISOs and security leaders, maintain accurate forecasts, and achieve quota on enterprise deals. Use Salesforce, Gong, Outreach or Apollo, Sales Navigator, and AI tools to support an efficient sales motion while providing feedback to product, marketing, and sales enablement teams.

Designs and deploys Pentera’s security validation platform in complex enterprise environments, leads penetration-testing and remediation deep dives, advises customers on threats and attack techniques, educates users, supports adoption and expansion, and relays customer feedback to Product, R&D, and Support teams.

Serve as a technical liaison between sales and customers, demonstrating Pentera's automated security validation, conducting demos, leading technical engagements, analyzing customer requirements, supporting on-site evaluations and post-sale adoption, collaborating with partners, and representing the company at events.

The company invites talented candidates to submit their CVs for future opportunities, even if no current openings match their qualifications.