Director, Enterprise Security Accounts — Midwest (Chicago)

Kai; Chicago (IL); Remote; USD 140,000 - 210,000; Full time

Job summary

Kai, the AI company rebuilding cybersecurity for the machine-speed era, is hiring a Director of Strategic Accounts for the Upper Midwest from Chicago. This hunter role builds pipeline from scratch, opens doors at Global 2000 and Fortune 500 accounts, and closes strategic deals that redefine the security landscape.

You’ll engage C-level security and IT leaders, run structured sales processes across multi-stakeholder cycles, and collaborate with product/engineering to bring customer insights into

Qualifications

• 8+ years of B2B enterprise software sales experience with a track record of closing 6- and 7-figure deals with Global 2000 or Fortune 500 accounts.
• Proven ability to hunt and build your own pipeline, open net-new logos, and not rely on inbound or existing relationships to hit your number.
• Startup or high-growth experience where the brand did not carry the deal and you earned every win.
• Background in cybersecurity or adjacent security categories with credibility with CISOs, security architects, and SOC leaders.
• Experience running consultative, multi-stakeholder sales cycles with C-level security and IT executives.
• Fluency in enterprise sales methodologies (MEDDICC, MEDDPICC, Force Management, Challenger, or equivalent).
• Based in Chicago with deep market knowledge and established Upper Midwest relationships.

Responsibilities

• Own the full sales cycle from prospecting to close across enterprise accounts in the Upper Midwest, focused on Chicago and surrounding markets.
• Build and manage your own pipeline as hunter, closer, and relationship owner.
• Engage CISOs, CIOs, security architects, and SOC leaders across security, IT, and compliance.
• Run a structured, outcome-driven sales process through complex enterprise deals.
• Collaborate with Solutions Engineering to deliver compelling demonstrations and POVs.
• Work with Product and Engineering to feed field intelligence back into the roadmap as the voice of the customer.

Skills

Enterprise software sales

Closing large deals

Pipeline development

Executive engagement

Multi-stakeholder selling

MEDDICC/CHALLENGER

Chicago Upper Midwest knowledge

Tools

MEDDICC

Job description

Kai, the AI company rebuilding cybersecurity for the machine-speed era, is hiring a Director of Strategic Accounts for the Upper Midwest from Chicago. This hunter role builds pipeline from scratch, opens doors at Global 2000 and Fortune 500 accounts, and closes strategic deals that redefine the security landscape.

You’ll engage C-level security and IT leaders, run structured sales processes across multi-stakeholder cycles, and collaborate with product/engineering to bring customer insights into