Account Executive

About the role

The Account Executive role at Coworker is responsible for driving AI adoption for organizations under 1,000 employees. This includes converting self-serve signups into strategic, multi-seat contracts, hunting and generating pipeline, prospecting and qualifying, and delivering tailored ROI-focused demos.

Responsibilities

• Manage 30–40 opportunities monthly, from qualification through close (1–2 month cycles).
• PLG Conversion: Convert self-serve signups into strategic, multi-seat contracts.
• Hunt & Generate Pipeline: Proactively identify and engage target accounts; generate 50%+ of your own pipeline through strategic outbound hunting.
• Prospect & Qualify: Partner with the Growth team; supplement inbound with daily outbound activities.
• Discovery & Demo: Map pain points to platform capabilities; deliver tailored ROI-focused demos.
• Deal Strategy: Navigate multi-stakeholder deals using MEDDIC/BANT; overcome objections on budget, security, integration.
• AI Advisory: Advise organizations implementing AI across teams using tools like Claude, ChatGPT, and other platforms — optimizing existing AI investments alongside Coworker.

Requirements

• Experience: 2–4 years in SaaS closing roles (SDR/BDR promotion preferred); consistent 75%+ quota attainment; familiarity with mid-market sales cycles (30–60 days).
• Sales Skills: Strong prospecting instincts, negotiation skills, and ability to articulate technical value propositions clearly to both technical and non-technical buyers.
• AI Fluency: Hands-on experience with AI tools beyond basic chat (Claude, ChatGPT, Cursor, etc.) — ability to advise customers on implementing AI efficiently across their organization alongside other tools.
• Mindset: Hustle, ownership, hunger to learn, coachable attitude, and resilience in ambiguous, fast-changing environments.
• Competitive Drive: Extremely competitive and self-motivated with a track record of overachievement.

Preferred Qualifications

• 1+ years selling to mid-market or enterprise SaaS
• Familiarity with AI and Enterprise AI landscape
• Experience with PLG motion or product-led sales
• Existing relationships in the SMB/Mid-Market B2B SaaS ecosystem

Compensation & Benefits

• OTE: $210,000–$240,000 (50/50 base/variable split)
• Base Salary: $105,000–$120,000
• Variable Commission: $105,000–$120,000+ (uncapped accelerators for overperformance)
• Equity: Extremely generous equity in early-stage company
• Ramp: Structured ramp program with guaranteed draw
• Benefits: Health/dental/vision insurance, 401(k), unlimited PTO

Career Development

• Mentorship: Paired with senior AEs for deal reviews and skill-building
• Promotion Path: Clear trajectory to Enterprise AE or Team Lead within 18–24 months
• Training: Workshops on MEDDIC, AI tooling and analysis, and startup autonomy

About Coworker

Coworker.ai is an equal opportunity employer. We believe everyone should feel great about being their authentic selves at Coworker — this is the only way to do our best work. We encourage you to apply even if you feel over- or under-qualified. We want to find the best people to help us build the future of work, no matter who they are.