Senior Account Executive

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.

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. 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 do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We believe that great employees come from diverse backgrounds.