Strategic Account Executive (Chicago)

As a Strategic Account Executive at Rox, you'll be responsible for bringing the world's best revenue teams into the age of AI. You'll lead highly consultative, value-driven sales cycles with C-level decision-makers at fast-growing startups and established enterprises.

Responsibilities

Own the full sales cycle: from qualification to negotiation to close; Develop deep understanding of each prospect's revenue workflows and pain points; Lead tailored product demos and build compelling value narratives; Collaborate with product and solutions teams to shape roadmap and integrations; Continuously refine messaging and materials based on what resonates in the field; Help shape the GTM engine at Rox, from process to tooling to playbooks; Represent Rox with clarity, energy, and urgency in every interaction

Requirements

4+ years of strategic sales experience closing large, complex enterprise deals; Sold to enterprise buyers in a value-based, consultative sales motion; Playbook Experience at Command of Message or Value Selling Organization; High learning velocity and intellectual curiosity: you dig deep and RTFM; Proven ability to operate in early-stage or high-ambiguity environments (teams <150 people); Builder mindset: you run your deals like products; Coachable, thoughtful, and obsessed with getting better every week

Benefits

Competitive pay with considerable equity upside; Medical, dental, and vision, including 100% company-paid plans for you and eligible dependents; Company-paid life & AD&D, plus short- and long-term disability; 401(k) with automatic enrollment; Unlimited PTO, plus paid sick leave, company holidays, and bereavement; Up to 20 weeks of paid parental leave at 100% pay (birth, adoption, or foster); Wellness stipend: $375/quarter; Learning stipend: up to $2,000/year; Internet & cell phone stipend: $25/month; Mental health support, virtual care, and care navigation; Fertility & family-building support, plus backup care membership; Pre-tax commuter benefits (transit & parking); SF HQ: daily catered breakfast & lunch, meal allowances, and rideshare support when commuting to the office