Director of Strategic Accounts, Upper Midwest (Chicago)

Kai is the AI company rebuilding cybersecurity for the machine-speed era. Founded by second time founders and trusted by Fortune 500 enterprises, Kai is building a future where security has no categories, no silos, and no human speed bottlenecks. The Kai Agentic AI Platform replaces fragmented, human-limited workflows with agentic AI systems that continuously contextualize, assess, reason, and execute security work at machine speed - making human defenders, superhuman.

Why Join Kai

• Well-funded: With $125M raised, we have the capital, runway, and resolve to rebuild cybersecurity from first principles.
• Proven: We've earned the trust of Fortune 500 and Global 1000 companies, and we're just getting started. Their confidence in Kai reflects what we've built: an AI-powered cybersecurity platform that performs at the scale and speed the enterprise demands.
• Experienced founders: Our founding team consists of second-time entrepreneurs, each with over 20 years of experience in the cybersecurity industry. Their proven expertise and vision drive our ambitious goals.
• World-class leadership team: Our Heads of AI, Engineering, and Product bring extensive experience from some of the world’s most influential companies, ensuring top-tier mentorship, direction, and vision.
• Frontier AI Applied Research Team: Our researchers operate at the leading edge of agentic AI systems, translating breakthrough capabilities into real-world cybersecurity applications.
• Generous compensation: We offer highly competitive salaries, equity options, and a supportive work environment. Your contributions will be valued and rewarded as we grow together.

LOCATION: Chicago, IL — remote, field-based.

THE ROLE

Kai is hiring a Director of Strategic Accounts to own the Upper Midwest territory out of Chicago. This is a hunter role — you are building pipeline from scratch, opening doors at the largest enterprises in the market, and closing deals that matter.

You will work directly with security leaders at Global 2000 and Fortune 500 accounts, navigating complex multi-stakeholder sales cycles and bringing a genuinely new category of AI-native security platform to market. This is not a role for someone who lets the brand do the work. Kai is early, ambitious, and winning — and the person who joins now will have direct influence on how the sales motion is built.

WHAT YOU'LL DO

• Own the full sales cycle from prospecting to close across enterprise accounts in the Upper Midwest territory, with a focus on Chicago and surrounding markets
• Build and manage your own pipeline — you are the hunter, the closer, and the relationship owner
• Engage C-level decision-makers across security, IT, compliance, and engineering — CISOs, CIOs, security architects, and their teams
• Run a structured, outcome-driven sales process through complex, multi-stakeholder enterprise deals
• Collaborate with Solutions Engineering to deliver compelling demonstrations and manage POVs that are measured against customer business outcomes
• Work closely with Product and Engineering to bring field intelligence back into the roadmap — you are the voice of the customer inside the company
• Provide real-time feedback on messaging, pricing, and competitive positioning as Kai's go-to-market motion continues to evolve

WHAT YOU'LL BRING

Required:

• 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 — you build your own pipeline, open net-new logos, and don't rely on inbound or existing relationships to hit your number
• Startup or high-growth company experience — you have sold in an environment where the brand didn't carry the deal, and you earned every win
• Background in cybersecurity or adjacent technical security categories — you can speak credibly to CISOs, security architects, and SOC leaders
• Deep experience running consultative, multi-stakeholder sales cycles with C-level security and IT executives
• Fluency in a formal enterprise sales methodology — MEDDICC, MEDDPICC, Force Management, Challenger, or equivalent
• Based in Chicago with deep market knowledge and established relationships in the Upper Midwest

Preferred:

• Experience selling into accounts undergoing security modernization or AI-driven transformation initiatives
• Familiarity with AI-native platforms or emerging security technology categories

#LI-Remote

Kai is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. 

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