Account Executive; Enterprise Track

InRule Technology®, Inc. is a PE-backed SaaS company with hundreds of customers in more than 40 countries. Our integrated Decision Intelligence Platform (DIP) combines decisioning, process automation, and machine learning to help IT and business leaders make better decisions faster, operationalize AI, and improve complex processes.

We are trusted by some of the world’s largest banks, insurance companies, healthcare organizations, and governments for mission-critical applications. By making automation accessible, InRule increases productivity, drives revenue, and delivers exceptional business outcomes.

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.

• 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.

• 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.

• Pipeline coverage and conversion rates.
• Forecast accuracy.
• Sales methodology adherence.

• $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.

The pay range for this role is:

95,000 - 95,000 USD per year (InRule Chicago)