Enterprise Account Executive

Enterprise Account Executive – Midwest

Next-Generation Software Infrastructure

Location : Chicago, Illinois (Fully Remote – Must Be Chicago-Based)

Up to $320k OTE (50/50 Split) + Equity

Summary

Join a rapidly scaling software company tackling some of the most complex challenges facing modern enterprise technology teams.

The business works with technically sophisticated organisations and is entering a significant phase of growth, investing heavily in its commercial operations across the US and internationally.

As an Enterprise Account Executive, you'll take ownership of a strategically important Midwest territory, developing relationships with senior technical leaders and C-level executives across large enterprise organisations.

You'll lead complex, high-value sales cycles from initial engagement through to close, with dedicated business development and technical support behind you.

This is an opportunity for a commercially ambitious, technically curious seller to take genuine ownership of their territory and play a meaningful role in shaping a growing US business.

What you'& achieve

• Own the full enterprise sales cycle, with a focus on new-logo acquisition
• Develop and execute strategic account plans across the Midwest
• Build relationships with senior technical decision-makers and C-level executives
• Lead complex discovery conversations, identifying technical challenges and commercial priorities
• Navigate multi-stakeholder enterprise opportunities and lengthy sales cycles
• Build and manage a strong, self-generated pipeline
• Translate sophisticated technology into measurable business outcomes
• Collaborate closely with Sales Engineering, Business Development and leadership
• Contribute to territory strategy and wider GTM initiatives
• Deliver consistent revenue performance through disciplined deal execution

Who you are

• 3+ years of enterprise B2B SaaS or technology sales experience
• Demonstrable track record of exceeding quota and winning new enterprise customers
• Experience selling sophisticated technology into complex enterprise environments
• Confident engaging both technical practitioners and executive decision-makers
• Strong discovery, qualification and consultative selling capabilities
• Proven ability to independently generate pipeline and develop strategic accounts
• Commercially driven, intellectually curious and comfortable with ambiguity
• Background in infrastructure, cloud, data, developer platforms or other technical software is advantageous
• Must be based in Chicago, with the ability to travel across the Midwest

Why Consider it

• Join a rapidly scaling software business at an exciting stage of international expansion
• Take ownership of a strategically important Midwest enterprise territory
• Up to $320k OTE (50/50 split), equity and accelerators
• Work on complex, high-value enterprise opportunities with sophisticated customers
• Dedicated Business Development and Sales Engineering support
• Fully remote, with approximately 25-40% customer travel
• Comprehensive benefits including employer-paid healthcare, 401(k) matching and unlimited PTO for exempt employees
• Genuine autonomy, direct leadership exposure and the opportunity to influence US growth

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