Enterprise Account Executive, Upper Mid-Market

What you'll do

Own new business sales across an assigned book (200–300 accounts), with a meaningful share of pipeline self-sourced through your own outbound motion, in partnership with your BDR

Run full-cycle Enterprise deals — multi-thread across the buying committee, quarterback internal resources (Product, SE, CS, Support, Executives), and orchestrate the deal from first outbound to close

Get prospects to quantify their own pain — build simple, back-of-napkin ROI models in real time and anchor the close on financial outcomes, not features

Negotiate and close annual contracts ranging $50K–$1M

Own post-sale activation planning — document ramp milestones and consumption targets before the deal closes, and set the CS team up to execute against them

Use AI tools operationally to run your business — account research, pipeline management, and prospecting, not just experimentation

Develop internal champions and sell the deal internally when you need resources or approvals

Travel to meet prospects and customers at events, meals, or their facilities

What you bring

• Proven track record closing new Enterprise accounts with complex organizational structures, including multi-year quota attainment you can speak to specifically
• A real, self-sourced outbound motion — not entirely dependent on inbound or BDR-sourced pipeline
• Experience selling to EVPs/CXOs and end-users within the same cycle, and communicating in an executive register
• Demonstrated ability to quantify business value and build ROI cases with prospects
• Experience owning post-sale handoff and ramp/activation planning, ideally in a consumptive or volume-based pricing model
• Resourcefulness — you find the answer rather than waiting for SE/CS/BDR bandwidth that isn't guaranteed
• Operational, hands-on use of AI tools to scale your own output
• Excellent written and verbal communication skills, with the ability to simplify complex topics
• Experience selling B2B solutions, preferably to HR buyers
• An A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes