Senior Account Executive
About the role
The Senior Account Executive will own strategic AI adoption for Mid-Market and Enterprise organizations, from first meeting to multi-year expansion. They will generate 50%+ of their own pipeline through strategic outbound hunting, 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), develop multi-threaded relationships using MEDDPICC or Challenger, lead discovery, demos, and ROI-focused business reviews, navigate complex technical evaluations, articulate architecture, security, and integration value to technical buyers, advise organizations on implementing AI efficiently across their enterprise, identify and execute upsell/cross-sell opportunities, build multi-year expansion roadmaps, maintain 90%+ forecast accuracy, deliver weekly pipeline reviews, and iterate playbooks to optimize conversion.
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.
- 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.
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
Skills
- Mastery of value-based selling, negotiation, and contract structuring
- Ability to discuss architecture, security, APIs, and integration patterns
- Hands-on experience with AI tools beyond basic chat
- Deep understanding of enterprise AI landscape
- Comfort selling to technical buyers
- Thrive in ambiguity
- Balances short-term wins with long-term account management
- Highly-tuned owner's mentality
- Extremely competitive and self-motivated
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
Pay
$250,000–$280,000 (50/50 base/variable split)
Schedule
Hybrid/Remote Flexibility