Built by ex–nation-state operators and AI researchers, Cracken is building the world’s first Uncensored Vibe Hacking platform — safely amplifying security teams with autonomous offensive security capabilities and delivering proven, auditable resilience for modern enterprises.
We are growing fast and looking for a Sales Engineer to help shape the future of AI-driven cybersecurity.
ResponsibilitiesDemonstrate deep expertise in cybersecurity, AI Agents, offensive security methodologies, and modern enterprise security environments
Lead customer-facing engagements, including intro calls, technical deep dives, workshops, and product evaluations
Partner closely with the sales team to develop account strategies, support pipeline growth, and drive successful deal execution
Deliver compelling technical product demonstrations for prospects and customers, clearly articulating both technical and business value
Work alongside channel and strategic partners to expand customer success and technical enablement initiatives
Analyze customer requirements, answer technical questions, and align Cracken’s platform capabilities with real-world security challenges
Represent Cracken at conferences, trade shows, community events, and customer meetings as a trusted technical expert
Support successful proof-of-concepts, onboarding, deployments, and post-sale technical relationships
3+ years of experience in Pre-Sales, Sales Engineering, Technical Account Management, Solutions Engineering, or Professional Services — ideally within a cybersecurity or AI startup environment
Strong understanding of cybersecurity concepts, offensive security methodologies, and AI Agents
Familiarity with penetration testing workflows and attacker mindsets; hands-on experience is a strong advantage
Ability to communicate complex technical concepts clearly to both technical and business stakeholders
Experience supporting enterprise customers throughout the sales cycle
Certifications such as CEH, CISSP, OSCP, or similar are a plus
Comfortable working in fast-moving, high-ownership startup environments
Availability for occasional travel
BSc. in Engineering, Computer Science, Cybersecurity, or related field preferred
Real-world impact: our technology is shaped by offensive security expertise, real operational experience, and deep internal research
Mission-driven team: international team with strong Ukrainian roots, bringing together researchers, engineers, professors, and elite cyber operators
High ownership culture: exceptional people shape their own scope and trajectory inside the company
Frontier technology: operating at the intersection of AI, autonomous systems, and cybersecurity
Fast execution: small elite team, minimal bureaucracy, direct collaboration with founders
Ownership over a cutting-edge cybersecurity platform
Direct access to founders, researchers, and experienced offensive security professionals
High autonomy and real influence on product and go-to-market direction
Fully remote and flexible work environment
Competitive compensation package
Similar Jobs
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory


