Enterprise Account Executive

Weekday; San Francisco (CA); On-site; USD 120,000 - 180,000; Full time

Benefits offered by this job

Medical insurance

401(k) plan

Unlimited PTO

In-office lunch

Job summary

Weekday is seeking an experienced Enterprise Account Executive in San Francisco to lead the full sales cycle for strategic B2B SaaS opportunities. You will partner with SDRs, manage discovery conversations with senior executives, navigate complex buying processes, negotiate contracts, close deals, and identify expansion opportunities.

The ideal candidate has a strong background in B2B SaaS sales, excels at building relationships with senior executives, and can translate customer challenges into

Qualifications

• 6–10 years of experience in B2B SaaS sales at enterprise level.
• Proven track record selling to senior executives and managing multi‑stakeholder cycles.
• Strong discovery skills to identify business challenges and urgency.
• Ability to build compelling business cases linking product capabilities to measurable results.
• Excellent follow‑up, pipeline management, and CRM discipline.
• Strong communication and presentation skills with ability to simplify complex concepts.

Responsibilities

• Own the Full Sales Cycle: manage enterprise opportunities from prospecting through discovery, negotiations, closure and growth.
• Lead Discovery Conversations with CROs and senior stakeholders to understand business priorities and pain points.
• Identify Business Opportunities by mapping decision processes and defining measurable impact.
• Manage Complex Deals with cross‑functional teams (security, legal, procurement, exec) to drive progress.
• Drive Deal Momentum with structured follow‑ups and clear mutual action plans.
• Develop Sales Playbooks and refine enterprise messaging, demos, and business cases.
• Collaborate Cross‑functionally with founders, Product and Marketing to improve GTM and product positioning.
• Build Executive Relationships by communicating ROI in strategic terms.
• Operate with Ownership by identifying opportunities and evolving sales processes in a dynamic environment.

Skills

Enterprise sales

B2B SaaS

Stakeholder management

Contract negotiations

CRM proficiency

Discovery & qualification

Job description

This role is for one of Weekday's clients

Min Experience: 6+ years
Location: San Francisco
JobType: full-time

We are looking for an experienced Enterprise Account Executive to drive business growth by managing the complete sales cycle across strategic and enterprise accounts. This role involves partnering with Sales Development Representatives (SDRs) on prospecting, leading discovery conversations, navigating complex buying processes, negotiating contracts, closing deals, and identifying opportunities for account expansion.

The ideal candidate has a strong background in B2B SaaS sales, excels at building relationships with senior executives, and can translate complex customer challenges into measurable business outcomes. You will collaborate closely with senior revenue leaders, founders, Product, and Marketing teams to refine sales strategies, incorporate customer feedback, and build a scalable enterprise go-to-market (GTM) strategy.

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

Key Responsibilities

• Own the Full Sales Cycle: Manage enterprise sales opportunities from account planning and prospecting through discovery, security reviews, negotiations, deal closure, and account growth.
• Lead Discovery Conversations: Engage with CROs, Vice Presidents of Sales, Revenue Operations (RevOps) leaders, and other senior stakeholders to understand their business challenges and priorities.
• Identify Business Opportunities: Uncover customer pain points, establish urgency, understand buying criteria, map decision‑making processes, and define measurable business impact.
• Manage Complex Deals: Build consensus across business, technical, security, legal, procurement, and executive teams to facilitate successful deal progression.
• Drive Deal Momentum: Maintain structured follow‑ups, establish clear mutual action plans, coordinate next steps, and ensure accurate CRM documentation.
• Develop Sales Playbooks: Contribute to the development and refinement of enterprise sales processes, messaging, demonstrations, and business cases.
• Collaborate Cross‑functionally: Share customer insights with founders, Product, and Marketing teams to improve product positioning, sales effectiveness, and go‑to‑market execution.
• Build Executive Relationships: Establish trust with decision‑makers and communicate product value in terms of strategic priorities and measurable business outcomes.
• Operate with Ownership: Identify new opportunities, experiment with sales approaches, and continuously improve processes in a dynamic environment.

Required Qualifications

• 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, with the ability to identify underlying business challenges, customer priorities, and purchasing urgency.
• Proven 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, with the ability to simplify complex concepts and communicate a compelling customer value proposition.
• Highly coachable, receptive to feedback, and capable of adapting sales strategies quickly.
• Experience working in early‑stage companies or ambiguous, rapidly evolving business environments.
• An ownership‑driven mindset, with the ability to generate opportunities and build effective sales processes without relying on a fully established playbook.

Good‑to‑Have Qualifications

• 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 GTM strategies.

Benefits and Perks

• 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.