Account Executive

Weekday AI · San Francisco, CA

Base: Not disclosed
OTE: Not disclosed
Quota attainment: Not disclosed
Posted: 11d ago

Why it matters: OTE tells you what you could earn. Attainment tells you how realistic it is.

Ask: “What percentage of fully ramped reps hit quota last year?”

Still open · checked 2h agoon Weekday AI's careers page

Apply on Weekday AI →

The job

What you'd do: Sell software to very big companies in San Francisco, working with senior executives from first call to signed deal. You'll share the search for new customers with sales development reps.
Who you'd sell to: CROs, VPs of Sales and RevOps leaders at big companiesIn their words: “Engage with CROs, Vice Presidents of Sales, Revenue Operations (RevOps) leaders, and other senior stakeholders”
Where deals come from: A mix. Some leads come to you, some you find yourself.

The Braun Read

Ask hard questions

Too much is left unsaid. Make them answer before you invest.

Pay: No pay listed at all.
Transparency: Says nothing about quota, attainment, deal size, territory or sales cycle.
Time on market: Open 11 days.
Company hiring: 10 sales roles open, hiring at a steady pace.

Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

1.
What percentage of fully ramped reps hit quota last year?
OTE is what you could earn. This is how likely you are to earn it.
2.
What percentage of reps on the team have been here more than 18 months?
Tenure shows whether people stay long enough to get paid.
3.
Has the comp plan changed in the last 12 to 18 months? What changed?
A plan that changes every year means the goalposts keep moving.
4.
Who sits with reps and reviews calls each week?
Coaching is often what's behind a good or bad attainment number.
5.
What are the base and the OTE for this role?
No point investing hours before you know the number.
6.
Why is this role open? Did someone leave, or is it new?
New headcount is growth. A replacement means someone left. Ask why.

› When the offer comes

Save these for later. They land better once they've said yes to you.

1.
Can I see the full comp plan in writing, including clawbacks and accelerators?
What's in writing is what gets paid. Read it before you sign.
2.
Can I see the actual comp distribution for the team last year, not just the OTE?
The spread shows what most reps really take home. OTE is just the target.
3.
I'd be walking away from earned commission to join. Is there room for a sign-on bonus to help cover that?
Leaving money behind is a fair reason to ask. The worst answer is no.

Josh's top five questions for any sales interview →

Going for your first AE role? Get the free interview kit → 24 questions, what good and bad answers sound like, and an offer comparison sheet.

Got an offer from Weekday AI? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh

Full posting

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. Requirements 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.

Apply →