Strategic Accounts Director — AI Cybersecurity (Remote Upper Midwest)

Kai; Chicago (IL); Híbrido; USD 180.000 - 260.000; Jornada completa

Ventajas ofrecidas por este puesto de trabajo

Generous compensation

Equity options

Supportive work environment

Descripción de la vacante

Kai in Chicago is seeking a Director of Strategic Accounts to own the Upper Midwest territory. This hunter role focuses on building pipeline from scratch, opening doors at large enterprises, and closing meaningful deals.

You will engage security leaders at Global 2000 and Fortune 500 accounts, navigating multi-stakeholder sales cycles and introducing an AI-native security platform to market. Kai is early, ambitious, and offers direct influence on the sales motion.

Formación

• 8+ years of B2B enterprise software sales experience.
• Proven ability to hunt — you build your own pipeline and open net-new logos to hit your number.
• Startup or high-growth company experience — you earned every win without relying on brand power.
• Background in cybersecurity or adjacent technical security categories.
• 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.

Responsabilidades

• 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.

Conocimientos

Enterprise software sales

Pipeline development

Startup experience

Cybersecurity knowledge

C-level selling

MEDDICC/Challenger

Chicago Upper Midwest knowledge

Descripción del empleo

Kai in Chicago is seeking a Director of Strategic Accounts to own the Upper Midwest territory. This hunter role focuses on building pipeline from scratch, opening doors at large enterprises, and closing meaningful deals.

You will engage security leaders at Global 2000 and Fortune 500 accounts, navigating multi-stakeholder sales cycles and introducing an AI-native security platform to market. Kai is early, ambitious, and offers direct influence on the sales motion.