Position: Senior Account Executive

Location: San Francisco, CA / Atlanta, GA (Hybrid/Remote Flexibility)

Type: Full-Time

Experience: 5–7 Years in SaaS/AI Sales

Why Coworker?

Coworker is redefining how organizations work with AI. Our platform delivers the same chat, cowork, and code capabilities that enterprises need — at 80% lower cost with identical output quality. We do this by ensuring through our technology that every task has the right context and model to be completed most effectively. We're a fast-scaling startup with a powerful PLG engine and rapidly growing enterprise pipeline.

The Role

Own strategic AI adoption for Mid-Market and Enterprise organizations — from first meeting to multi-year expansion. We're seeking an experienced Senior Account Executive to own the full sales cycle for Mid-Market and Enterprise accounts. You'll navigate complex, multi-stakeholder deals, align our solution with executive-level strategic goals, and drive both new customer acquisition and expansion. This role requires a blend of hunter mentality, consultative selling, and cross-functional collaboration with the Growth team, Product, Engineering, and Customer Success.

What You'll Do

Hunt & Generate Pipeline: Proactively identify and engage target accounts; generate 50%+ of your own pipeline through strategic outbound hunting.

Revenue Generation: Identify, qualify, and close new business targeting VP/C-level decision-makers. Manage 25–30 opportunities with deal sizes of $50k–$300k+ ARR (1–3 month cycles).

Enterprise Strategy: Develop multi-threaded relationships using MEDDPICC or Challenger; lead discovery, demos, and ROI-focused business reviews.

Technical Selling: Navigate complex technical evaluations; articulate architecture, security, and integration value to technical buyers (CTOs, CISOs, VP Engineering).

AI Advisory: Advise organizations on implementing AI efficiently across their enterprise using tools like Claude, ChatGPT, Cursor, and other platforms — optimizing existing AI investments alongside Coworker.

Account Expansion: Identify and execute upsell/cross-sell opportunities; build multi-year expansion roadmaps.

Forecasting: Maintain 90%+ forecast accuracy; deliver weekly pipeline reviews; iterate playbooks to optimize conversion.

Requirements

Experience: 5–7 years full-cycle SaaS sales; verifiable $1M+ annual quota attainment; 2+ years in Enterprise/Mid-Market ($50k+ ACV).

Sales Acumen: Mastery of value-based selling, negotiation, and contract structuring; articulate technical solutions to non-technical buyers.

Technical Fluency: Comfort selling to technical buyers; ability to discuss architecture, security, APIs, and integration patterns.

AI Fluency: Hands-on experience with AI tools beyond basic chat (Claude, ChatGPT, Cursor, etc.) — deep understanding of enterprise AI landscape; ability to position Coworker within a broader AI strategy.

Adaptability: Thrives in ambiguity; balances short-term wins with long-term account management.

Ownership & Drive: Highly-tuned owner's mentality; extremely competitive and self-motivated.

Preferred Qualifications

Experience at a Series A/B/C SaaS startup

Familiarity with Enterprise AI landscape and competitive positioning

Existing relationships with Mid-Market and Enterprise B2B SaaS accounts

Experience selling platform/multi-product solutions

Compensation & Benefits

OTE: $250,000–$280,000 (50/50 base/variable split)

Base Salary: $125,000–$140,000

Variable Commission: $125,000–$140,000+ (uncapped accelerators)

Equity: Extremely generous early-stage equity

Benefits: Health/dental/vision, 401(k), unlimited PTO

Career Development

Leadership Path: Clear trajectory to Sales Leadership or Strategic Accounts Director

Executive Exposure: Regular interaction with founders and executive team on GTM strategy

Training: Advanced MEDDPICC, executive negotiation, 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 — this is the only way to do our best work. Apply even if you feel over- or under-qualified. We want the best people to build the future of work.