Enterprise Account Executive

Enterprise Account Executive

Gumloop is seeing massive enterprise adoption. We’re looking for a seasoned Enterprise Account Executive (AE) to help lead this growth and build the systems to help us grow even faster.

What You’Ll Do

• Own the entire sales process from prospecting to close for Fortune 1000 companies with deal sizes in the six to seven figure range.
• Navigate complex sales cycles, including procurement, legal, security, and multiple stakeholder groups across functions and levels.
• Capture customer feedback and partner with product to shape Gumloop’s roadmap.
• Outbound to target accounts to build and maintain a healthy pipeline of strategic opportunities.
• Qualify opportunities rigorously, ensuring the right prospects enter the funnel.
• Experiment with tactics to drive urgency, remove friction, and accelerate deals.
• Run high-converting pilots/POCs that demonstrate business value and expand into enterprise-wide rollouts.
• Forecast consistently and accurately, providing visibility to leadership.
• Evangelize Gumloop, acting as both a brand ambassador and trusted advisor.
• Be a consultative partner, bringing automation best practices and strategic insights to every conversation.
• Help build the sales machine — including playbooks, processes, materials, and templates.

What We’Re Looking For

• Proven experience selling enterprise SaaS products at a high-growth startup, ideally in workflow automation, integration, or adjacent categories.
• Track record of success navigating 6–7 figure enterprise deals with a dozen or more stakeholders, complex procurement, and long sales cycles.
• Builder’s mindset — comfortable creating process where none exists, iterating quickly, and influencing strategy.
• High EQ and strong consultative skills, capable of building deep relationships at both executive and practitioner levels.
• Relentless drive and ownership — willing to roll up your sleeves and do whatever it takes to win key accounts.

Why Gumloop

• Join a fast-growing startup at an inflection point, with the opportunity to shape both the sales org and the company trajectory.
• Work directly with the founders, influencing go-to-market strategy.
• Competitive compensation with salary + commission + meaningful equity.
• The chance to be a the first sales leader and define how enterprise sales at Gumloop is done.

(This role could either be at our SF or Vancouver Canada office but the work is in-person)