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Enterprise Account Executive (Chicago or Charlotte)

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.

📍 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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CEO of Rossum
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Tomas Gogar
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Average salary estimate

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$80000K
$120000K

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

Join Rossum as an Enterprise Account Executive, and become a key player in transforming the way businesses manage document processing and automation with our cutting-edge AI-powered platform! Based in Chicago or Charlotte, you will be at the forefront of our growth in the US market, where we are rapidly expanding our reach. Your mission will be to develop and execute an effective sales strategy aimed at exceeding revenue targets by connecting with decision-makers in finance, operations, and IT sectors across various enterprise organizations. You will manage the entire sales process from prospecting to closing deals while collaborating with C-level executives and procurement teams to understand their pain points and present Rossum as a game-changing solution for their needs. By leveraging our partnerships and alliances, you will drive sales while working side by side with our marketing, product, and customer success teams to enhance product adoption. We believe a successful Enterprise Account Executive possesses strong relationship-building skills, a solid understanding of SaaS sales, and the ability to navigate complex sales cycles. If you are driven by results and excited about the opportunities AI and automation bring to the enterprise space, then come help us scale operations and improve efficiency at Rossum!

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

As an Enterprise Account Executive at Rossum, your primary responsibilities will include developing and executing strategic sales plans to exceed revenue targets in the US market. You'll identify, prospect, and build relationships with key decision-makers in enterprise organizations. Managing the entire sales cycle from prospecting to close, you’ll engage closely with C-level stakeholders, negotiate contracts, and deliver compelling product demos to showcase Rossum's innovative AI solutions.

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What qualifications do I need to apply for the Enterprise Account Executive position at Rossum?

To become an Enterprise Account Executive at Rossum, you should have a minimum of 3 years of experience in SaaS enterprise sales, ideally in areas such as document automation, AI, or workflow transformation. A strong grasp of channel sales and structured sales methodologies, alongside excellent relationship-building skills and the ability to articulate Rossum’s value proposition, is vital for this role.

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How does Rossum’s AI-powered platform help enterprises in document processing?

Rossum’s AI-driven platform significantly streamlines document processing by eliminating manual data entry and automating workflows. This enhances efficiency across various industries, including finance, logistics, healthcare, and manufacturing, allowing companies to focus on strategic growth while our technology takes care of time-consuming document-heavy processes.

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What is the work environment like for an Enterprise Account Executive at Rossum?

The work environment for an Enterprise Account Executive at Rossum is dynamic and high-performance. The culture promotes accountability for achieving revenue targets and encourages collaboration among teams, including marketing, product, and customer success, to ensure client satisfaction and success in adopting our AI solutions.

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What makes Rossum different from other companies in the AI and automation space?

Rossum stands out in the AI and automation space by focusing specifically on intelligent document processing. Our platform’s capability to seamlessly integrate with other systems and adapt to various document workflows makes it a game-changer for enterprises looking to improve efficiency and reduce costs associated with manual data handling.

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Common Interview Questions for Enterprise Account Executive (Chicago or Charlotte)
How do you approach developing a strategic sales plan?

In approaching a strategic sales plan, I first analyze market trends and customer needs, then set clear and achievable revenue targets. I focus on identifying key decision-makers and tailor my outreach strategies to engage them effectively. Continuous monitoring and adaptation of the plan based on feedback and results are essential.

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Can you describe a time when you successfully closed a difficult deal?

Certainly! In a previous role, I faced a challenging deal with a lengthy procurement process. I cultivated strong relationships with multiple stakeholders through regular communication, addressed their concerns directly, and demonstrated how our solution aligned with their long-term goals, ultimately leading to a successful close.

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What techniques do you use to maintain relationships with clients?

I prioritize regular check-ins and provide value through insights and updates about our services. Building rapport over shared interests and offering personalized solutions helps foster lasting relationships, ensuring clients feel valued and supported long after the initial sale.

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How do you handle objections during the sales process?

I see objections as valuable opportunities to understand client concerns. I listen actively to their queries, empathize with their situation, and provide clear, factual explanations that demonstrate our product's strengths and how it can specifically address their pain points.

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What sales methodologies are you familiar with, and how do you apply them?

I am well-versed in methodologies like MEDDPICC and SPIN. I apply them by ensuring all stages of the sales cycle are executed methodically; for instance, using SPIN to ask situational questions that uncover client needs and developing a winning proposal based on their specific requirements.

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What tools and technologies do you utilize in your sales process?

I leverage CRM software to track leads, customer interactions, and sales metrics. Additionally, I utilize analytical tools to assess market data and tailor my outreach, alongside collaboration tools to ensure seamless communication with internal teams and stakeholders.

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How do you stay informed about trends in AI and automation?

I regularly read industry publications, attend webinars, and participate in professional networking groups focused on AI and automation. Staying connected with industry leaders and keeping up with emerging technologies allows me to have meaningful conversations with prospects about the latest advancements.

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Describe how you deliver product demos.

During product demos, I focus on understanding customer pain points and customizing the presentation to highlight specific features that address their needs. Engaging stakeholders through interactive sessions and encouraging questions keeps the demo dynamic and relevant.

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What motivates you as an enterprise sales professional?

I am motivated by the challenge of closing complex deals and the satisfaction of knowing I am helping organizations improve their processes and efficiencies. The ever-evolving technology landscape in AI and automation also fuels my passion for continual learning and growth in this field.

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How do you ensure you meet or exceed your revenue targets?

I set specific, measurable goals and continually analyze my progress throughout the sales cycle. By cultivating top-of-funnel activities, nurturing leads effectively, and consistently seeking referrals, I ensure a robust pipeline that enables me to meet and often exceed my revenue targets.

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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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Full-time, hybrid
DATE POSTED
March 28, 2025

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