Enterprise Account Executive

Weekday AI • San Francisco, CA

9d

About The Position

The Enterprise Account Executive will drive business growth by managing the complete sales cycle across strategic and enterprise accounts. The role includes partnering with Sales Development Representatives on prospecting, leading discovery conversations, navigating complex buying processes, negotiating contracts, closing deals, and identifying account expansion opportunities.

The successful candidate will bring a strong background in B2B SaaS sales, build relationships with senior executives, and translate complex customer challenges into measurable business outcomes. The role collaborates with senior revenue leaders, founders, Product, and Marketing to refine sales strategies, incorporate customer feedback, and build a scalable enterprise go-to-market strategy.

This is a high-ownership opportunity for a sales professional who thrives in a fast-paced, early-stage environment and can create opportunities while processes and playbooks are still evolving.

Requirements

• 6–10 years of experience in B2B SaaS sales, with a proven track record of success in enterprise sales.
• Demonstrated experience selling to senior executives and managing complex, multi-stakeholder sales cycles.
• Strong discovery skills, including the ability to identify underlying business challenges, customer priorities, and purchasing urgency.
• Ability to build compelling business cases and connect product capabilities to measurable business results.
• Excellent follow-up, pipeline management, and CRM management skills.
• Strong communication and presentation skills, including the ability to simplify complex concepts and communicate a compelling customer value proposition.
• Highly coachable, receptive to feedback, and able to adapt sales strategies quickly.
• Experience working in early-stage companies or ambiguous, rapidly evolving business environments.
• Ownership-driven mindset, with the ability to generate opportunities and build effective sales processes without relying on a fully established playbook.

Nice To Haves

• Experience selling to revenue, sales, or go-to-market leadership teams.
• Exposure to AI-focused organizations or AI-powered B2B SaaS solutions.
• Experience navigating enterprise procurement, security, and legal review processes.
• Experience developing enterprise sales methodologies, messaging frameworks, and scalable go-to-market strategies.

Responsibilities

• Manage enterprise sales opportunities from account planning and prospecting through discovery, security reviews, negotiations, deal closure, and account growth.
• Lead discovery conversations with CROs, Vice Presidents of Sales, RevOps leaders, and other senior stakeholders to understand business challenges and priorities.
• Uncover customer pain points, establish urgency, understand buying criteria, map decision-making processes, and define measurable business impact.
• Build consensus across business, technical, security, legal, procurement, and executive teams to advance complex deals.
• Maintain structured follow-ups, establish mutual action plans, coordinate next steps, and ensure accurate CRM documentation.
• Contribute to the development and refinement of enterprise sales processes, messaging, demonstrations, and business cases.
• Share customer insights with founders, Product, and Marketing to improve product positioning, sales effectiveness, and go-to-market execution.
• Build trusted relationships with decision-makers and communicate product value in terms of strategic priorities and measurable business outcomes.
• Identify new opportunities, experiment with sales approaches, and continuously improve processes in a dynamic environment.

Benefits

• Comprehensive medical, dental, and vision insurance coverage.
• 401(k) retirement savings plan.
• Unlimited paid time off (PTO).
• Daily in-office lunch and a fully stocked kitchen.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed