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.

- 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.

- 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.

- Existing relationships with Mid-Market and Enterprise B2B SaaS accounts

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

- 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

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.