Account Executive

Weekday; San Francisco (CA); On-site; USD 120,000 - 210,000; Full time

Benefits offered by this job

Medical insurance

401(k)

Unlimited PTO

Office lunch

Job summary

Weekday is seeking an experienced Enterprise Account Executive to drive growth by managing the full sales cycle across strategic accounts. You will partner with SDRs on prospecting, lead discovery conversations, negotiate contracts, close deals, and identify opportunities for account expansion.

The ideal candidate excels in B2B SaaS, builds relationships with senior executives, and translates complex challenges into measurable business outcomes.

Qualifications

• 6–10 years of experience in B2B SaaS sales.
• Experience selling to senior executives and managing complex, multi-stakeholder sales cycles.
• Strong discovery skills to identify underlying business challenges and priorities.
• Proven ability to build compelling business cases and connect product capabilities to outcomes.
• Excellent follow-up, pipeline management, and CRM management skills.
• Strong communication and presentation skills, able to simplify complex concepts.
• Highly coachable and adaptable in early-stage environments.
• Ownership mindset to generate opportunities without a fully established playbook.

Responsibilities

• Own the full sales cycle from account planning through discovery, negotiations, closing, and growth.
• Lead discovery conversations with CROs, VP Sales, RevOps, and other senior stakeholders.
• Identify business opportunities, establish urgency, and map decision-making processes.
• Manage complex deals by aligning business, technical, security, legal, procurement, and executive teams.
• Drive deal momentum with follow-ups and mutual action plans in CRM.
• Develop enterprise sales playbooks and refine messaging, demos, and ROI cases.
• Collaborate with founders, Product, and Marketing to improve GTM execution and positioning.

Skills

Enterprise sales

B2B SaaS sales

Executive engagement

Discovery skills

Negotiation

CRM management

Stakeholder management

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.