Senior Account Executive

About 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.

Responsibilities

• 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.
• 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.
• Drop us a line!
• We encourage you to drop us a line even if you feel over- or under-qualified. We want to find the best people to help us build Coworker no matter who they are. We have a lot of different areas of responsibility and we are always happy to brainstorm with you about what would be the best fit.

Benefits

Additional Information

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.

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