Founding Enterprise AE

Gumloop is seeing massive enterprise adoption. Companies like Shopify, Instacart, Doordash and Ramp are rolling out Gumloop company-wide. Currently all this growth has been through pure word of mouth.

We're building faster than anyone in the space and want to bring on a seasoned account executive to navigate our largest enterprise deals. This is a greenfield opportunity to go after hundreds of product qualified enterprise leads.

Read about what we believe here and see what a day in the life looks like here.

• 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.

• Outbound to target accounts to build and maintain a healthy pipeline of strategic opportunities.

• Partner with SDRs to develop account strategies, execute outreach, and qualify 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.

• Capture customer feedback and partner with product to shape Gumloop’s roadmap.

• Proven experience closing large enterprise SaaS deals at a high-growth startup

• Strong background in workflow automation, integration, or adjacent software categories

• Demonstrated success running complex multi-stakeholder sales processes with long cycles

• Strategic, consultative selling style with high emotional intelligence

• Builder mindset: thrives with autonomy, creates process where none exists, and improves fast

• Comfortable managing SDR support and mentoring early-career reps

• Resourceful, metrics-driven, and relentless about driving outcomes

• Help build the foundation for Gumloop’s enterprise sales function

• Direct access to founders and influence on GTM strategy

• Compensation structured for top performers with strong upside

• In-office roles in Vancouver or San Francisco

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