Director of Strategic Accounts, Upper Midwest (Chicago)

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