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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! 🚀

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Average salary estimate

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$120000K

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What You Should Know About Enterprise Account Executive (Chicago), Rossum

Rossum is looking for a talented Enterprise Account Executive to join our dynamic team in Chicago or Charlotte! We’re on a mission to transform how businesses handle document processing and automation with our cutting-edge AI-powered platform. As an Enterprise Account Executive at Rossum, you will play a crucial role in driving revenue growth by selling our innovative solution to enterprise clients across various industries like finance, logistics, healthcare, and manufacturing. You will develop and execute strategic sales plans, identify and build lasting relationships with decision-makers, and manage all aspects of the enterprise sales cycle. Your ability to understand customer pain points and effectively showcase how Rossum can streamline their document-heavy processes will be key to your success. Additionally, you will collaborate with marketing, product, and customer success teams to maximize adoption of our platform, while also negotiating contracts to ensure successful outcomes for both parties. If you thrive in a high-performance culture and have a passion for AI and automation, we can’t wait to meet you!

Frequently Asked Questions (FAQs) for Enterprise Account Executive (Chicago) Role at Rossum
What are the primary responsibilities of the Enterprise Account Executive at Rossum?

The primary responsibilities of the Enterprise Account Executive at Rossum include developing and executing strategic sales plans to exceed revenue targets, identifying and building relationships with decision-makers in enterprise organizations, managing the sales process from prospecting to closing, delivering product demos, and collaborating with cross-functional teams to drive product adoption.

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What qualifications are needed to apply for the Enterprise Account Executive position at Rossum?

Candidates applying for the Enterprise Account Executive position at Rossum should have at least 3+ years of experience in SaaS enterprise sales, particularly in document automation or AI. A solid understanding of channel sales, complex sales cycles, and experience with structured sales methodologies is also important. Strong relationship-building skills and the ability to articulate Rossum’s value proposition are essential.

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How does Rossum support its Enterprise Account Executives in achieving their sales goals?

Rossum supports its Enterprise Account Executives by providing them with a strategic sales plan, necessary resources, and access to marketing, product, and customer success teams. This collaborative environment helps executives position Rossum's solutions effectively to meet customer needs and drive revenue growth.

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What industries does the Enterprise Account Executive at Rossum primarily target?

The Enterprise Account Executive at Rossum primarily targets a variety of industries including finance, logistics, healthcare, and manufacturing, all of which benefit from our AI-powered document processing and workflow automation solutions.

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What benefits does Rossum offer to its Enterprise Account Executives?

Rossum offers a comprehensive benefits package for its Enterprise Account Executives including 20 days of vacation, medical, dental, and vision health benefits, a 401(k) with employer matching, flexible working hours, and an Employee Stock Option Plan.

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Common Interview Questions for Enterprise Account Executive (Chicago)
Can you describe your experience with enterprise sales in the SaaS industry?

When answering this question, highlight your relevant experience, discussing specific roles, sales achievements, and the sales methodologies you've employed to close deals in the SaaS landscape.

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How do you approach relationship building with C-level stakeholders?

Share your strategies for establishing rapport and building trust with C-level executives. Discuss how you listen to their needs, address pain points, and align your solution with their business objectives.

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What sales methodologies have you successfully utilized in your previous roles?

Discuss the sales methodologies you've used, such as MEDDPICC or SPIN, and provide examples of how these frameworks have helped you structure sales processes and achieve your targets.

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How do you handle objections during the sales cycle?

Explain your approach to navigating objections, such as actively listening to concerns, providing informative responses, and reinforcing the unique value propositions of your offering to overcome resistance.

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Can you give an example of a successful sales deal you closed?

When providing examples, focus on the entire process from prospecting to closure, including the challenges faced, your specific actions, and the outcome of the deal.

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What strategies do you use to identify new enterprise leads?

Discuss your methods for researching and identifying potential leads, leveraging tools, networking, and utilizing market trends to find opportunities in the enterprise sector.

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How do you keep yourself updated on industry trends and developments?

Mention any reading, professional groups, or events you follow to stay informed about industry trends in AI, document processing, and sales best practices, showcasing your commitment to continuous learning.

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How do you prioritize and manage your sales pipeline?

Explain your approach to managing your pipeline by discussing your criteria for prioritization and the tools you use to track progress and ensure timely follow-ups.

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What role does teamwork play in your sales process?

Emphasize the importance of collaboration with marketing and product teams, detailing how teamwork enhances your ability to provide tailored solutions and meet customer needs effectively.

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Why do you want to work at Rossum as an Enterprise Account Executive?

Articulate your enthusiasm for Rossum's AI-powered solutions and how your values align with the company mission. Discuss your desire to contribute to its growth in the US market through your sales expertise.

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B2B communication is one of the most complicated processes in modern society, because businesses interact by exchanging myriads of document types in different forms by using many different channels. Our goals are: -to create effortless collabora...

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DATE POSTED
April 11, 2025

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