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 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 sales executives and partners on Abnormal Security’s products, platform, and security posture - Obsessively drive customer satisfaction and successful business outcomes Must Have - 3+ years of Sales Engineering experience OR relevant industry experience - 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 Nice to Have - Experience with enterprise email security platforms (Proofpoint, Mimecast, Cisco, Barracuda, etc.) - 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 Cloud SaaS infrastructure including identity services such as Azure AD / Entra ID / Google Identity  - Ability to explain identity-driven and modern social engineering attacks and controls at an architectural level - Experience integrating SaaS platforms via OAuth and REST APIs  - Familiarity with SIEM platforms (Splu