MidMarket Sales Engineer (Chicago)

About the Role Abnormal AI is seeking an Mid-Market Sales Engineer to join our growing Sales Engineering team. As an Mid-Market Sales Engineer, you will serve as our customer’s primary technical contact, acting as a trusted technical advisor to security, email, and identity teams, crafting strategic, value-based business cases to win complex business opportunities and help organizations conquer their most intractable email and identity-driven security challenges. In partnership with Mid-Market Account Executives, you will be responsible for conducting in-person and remote product demonstrations, leading architecture-level technical discussions, articulating the technical and business value of Abnormal Security’s platform, and owning and driving successful outcomes for Enterprise-scale Proof of Value (POV) programs. The ideal candidate for this role will be located in the Chicago area and possess the following skill set: Ability to tie technology to measurable risk reduction and business outcomes at Enterprise scale Ability to influence senior security, IT, and executive stakeholders in both virtual and in-person settings High EQ; ability to read the room, engage stakeholders, demonstrate empathy, listen actively, and respond thoughtfully Ability to create value-driven presentations and tell compelling stories (PowerPoint, Google Slides) Strong discovery skills to uncover customer pain points, requirements, and strategic objectives Understand and construct presentations on new products and iterate rapidly. What You Will Do Serve as the technical authority and primary technical decision partner in enterprise sales cycles, from discovery through close, including full ownership of Proof of Value (POV) success criteria and outcomes Lead architecture-level conversations with security, email, and identity teams Run technical discovery that uncovers risk, not just requirements Conduct technical and competitive landscape research to effectively address customer questions and objections Confidently answer architecture-level and modern threat questions without deferring to Product or Engineering Articulate why legacy secure email gateways fail against social engineering and identity-based attacks Educate and implement AI Security solutions across email, identity, and other verticals in the security stack. Educate sales executives and partners on Abnormal Security’s products, platform, and security posture Obsessively drive customer satisfaction and successful business outcomes Must Have Sales Engineering experience OR relevant industry experience OR can demonstrate technical aptitude. Demonstrated ability to lead technical discovery and architecture discussions with security, infrastructure, identity and compliance teams Strong technical presentation and communication skills, both verbal and written Ability to see and present the “big picture,” uncover complex business challenges, and architect solutions to solve customer needs Ability to work independently in a fast-paced, high-impact sales environment Positive attitude, strong customer focus, and a high sense of ownership over customer results Solid technical understanding of SaaS security models including multi-tenant cloud environments Working knowledge of DNS, TCP/IP, TLS, and enterprise networking concepts as they relate to email and SaaS security Curiosity to understand not only that a product works, but how/why it works. Nice to Have Experience with enterprise email security platforms (Proofpoint, Mimecast, Cisco, Barracuda, etc.) Basic understanding of cyber security tools including: EDR, Firewall, SIEM, ITP, etc and how those tools work together. Technical background in messaging and internet security principles Hands-on experience with Microsoft Exchange Online / Microsoft 365 or Google Workspace Strong understanding of SMTP mail flow, MX records and mail routing Working knowledge of email authentication (SPF, DKIM, DMARC) and common failure modes Strong understanding of Clou…