Enterprise Account Executive (Chicago)

Rossum is transforming how businesses handle document processing and automation with our AI-powered platform. By eliminating manual data entry and streamlining workflows, we help enterprises across industries—from finance and logistics to healthcare and manufacturing—drive efficiency and scale operations.

The US market is Rossum’s fastest growing market and we’re looking for an Enterprise Account Executive based in Chicago or Charlotte to drive revenue growth by selling our solution to enterprise clients whilst working with the US team. 

What You’ll Do:

• Develop and execute a strategic sales plan to exceed revenue targets in the US market.

• Identify, prospect, and build relationships with decision-makers in finance, operations, and IT teams at enterprise organizations.

• Manage an enterprise sales motion from prospecting to close, working closely with C-level stakeholders and procurement teams.

• Leverage partnerships and alliances to drive sales, collaborating with technology and service partners to expand reach and accelerate deal cycles.

• Understand customer pain points across finance automation, supply chain, and other document-heavy processes, positioning Rossum as a game-changing solution.

• Work closely with marketing, product, and customer success teams to drive adoption

• Deliver product demos that showcase the efficiency and impact of our AI-driven platform.

• Negotiate pricing, contracts, and terms to achieve win-win outcomes.

• Keep up with trends in AI, automation, and intelligent document processing to drive meaningful conversations with prospects.

What You’ll Need:

• 3+ years of experience in SaaS enterprise sales, preferably in document automation, AI, or workflow transformation.

• Understanding of channel sales, alliances, and working with technology/service partners to influence deals.

• Ability to navigate long, complex sales cycles with multiple stakeholders.

• Experience using a structured sales methodology (e.g., MEDDPICC, Challenger, SPIN).

• Ability to build strong relationships, influence decision-makers, and articulate Rossum’s value proposition.

• Comfortable working in a high-performance culture with accountability for revenue targets.

What we offer:

• 20 days of vacation

• Health Benefits: Medical (Aetna), dental (Guardian) and vision (VSP)

• 401k: Employer matching 100% contribution of 100% of the employee deferral up to 6% of eligible compensation, made each pay period

• Flexible working hours

• Employee Stock Option Plan

📍 Location: We are hiring for this role in Chicago or Charlotte Metro Area. 

If you’re passionate about AI, automation, and driving enterprise growth, we’d love to hear from you! 🚀