Strategic Account Executive (Chicago)

The Team

Nothing is possible without the world-class team, assembled to redefine how businesses operate.

Core Principles

TASTE: CRAFT BEAUTIFUL EXPERIENCES.

No matter how small, we strive to make sure every detail is right. We care deeply about every interaction, both in terms of whether it helps the seller get the job done, but also how the product makes them feel. We get a visceral feeling when something is off and stop at nothing to make sure we make it right. We never settle, continuously exploring ways to delight sellers.

OBSESSION: COMMIT UNREASONABLY.

In all aspects of our craft, we commit. We not only are immediately reactive to customers’ requests but are proactive about driving value even before they ask. We are also obsessive about always learning and honing our craft, improving ourselves and product every single day.

ACTION: GET IT DONE.

Talking is easy but the difference comes from the execution. We lean heavily towards making thoughtful yet fast decisions and delivering immediately. We play in a field where trust is paramount. We earn the trust and right to empower the best sellers by forging a history of over-delivering on the promise at record speed.

Your Role

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. Every deal will be different. No playbooks, no scripts: just first principles thinking, deep technical curiosity, and a relentless drive to understand the customer’s pain and map Rox’s capabilities to their workflows.

This role is ideal for someone who thrives in ambiguity, moves fast, and wants to help define how AI-native platforms are sold and adopted. You’ll work closely with product, solutions, and leadership to continuously evolve our go-to-market motion, all while building long-term relationships with some of the most forward-thinking GTM teams in the world.

If you’re a high-agency seller with a technical edge and a builder’s mindset, we’d love to talk.

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

Qualifications

• 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

To apply, please fill out the application form. We're looking forward to connecting with you!