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 Follow Scout Global for more roles like this...