Account Executive (Enterprise Growth Track)

InRule • Chicago, IL

41d • $95,000 - $95,000 • Hybrid

About The Position

We are seeking a high-potential Account Executive based in Chicago who is ready to step into enterprise-level selling. This is a quota-carrying role focused on driving net-new enterprise bookings and developing the skills required to manage complex, multi-stakeholder sales cycles. The role is designed for a strong mid-market seller progressing into enterprise complexity, with structured support, methodology discipline, and executive exposure.

Requirements

• 3–5 years of B2B SaaS sales experience with consistent quota attainment.
• Experience closing mid-market or emerging enterprise software deals.
• Demonstrated progression toward managing increasingly complex sales cycles.
• Exposure to formal sales methodologies such as MEDDIC, Challenger, or Winning by Design.
• Ability to communicate both technical value (architecture, integration, scalability) and executive-level business impact (ROI, efficiency, risk mitigation).
• Strong coachability, intellectual curiosity, and executive presence.
• Desire to develop into a full enterprise-level seller.

Responsibilities

• Own and execute territory strategy to drive net-new enterprise bookings.
• Generate pipeline through disciplined outbound prospecting and account-based selling.
• Lead complex, multi-threaded sales cycles involving business and technical stakeholders.
• Apply a structured sales methodology (e.g., MEDDIC, Winning by Design, or equivalent) to qualify opportunities, identify economic buyers, and build quantified business cases.
• Develop strong champion relationships and advance opportunities through procurement and legal review.
• Establish executive alignment and position solutions against quantified business outcomes.
• Partner closely with Sales Engineering, Marketing, Product, and Customer Success to orchestrate coordinated deal strategies.
• Maintain rigorous CRM hygiene, pipeline discipline, and forecasting accuracy.
• Participate in structured deal reviews and coaching to accelerate enterprise capability development.

Benefits

• $95K Base / $95K Variable
• Chicago, IL (Hybrid – office and home). Flexible work environment.
• The opportunity to build and shape a premium support function with measurable customer impact.
• A collaborative culture with close partnership across Support, Engineering, Product, and Customer Success.
• Professional growth within a scaling SaaS organization.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 11-50 employees