Senior Account Executive

Coworker.ai•San Francisco, CA

9d•$250,000 - $280,000•Hybrid

About The Position

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. 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.

Requirements

5–7 years full-cycle SaaS sales; verifiable $1M+ annual quota attainment; 2+ years in Enterprise/Mid-Market ($50k+ ACV).
Mastery of value-based selling, negotiation, and contract structuring; articulate technical solutions to non-technical buyers.
Comfort selling to technical buyers; ability to discuss architecture, security, APIs, and integration patterns.
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.
Thrives in ambiguity; balances short-term wins with long-term account management.
Highly-tuned owner's mentality; extremely competitive and self-motivated.

Nice To Haves

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

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.