Account Executive, Enterprise (Chicago)

Ladders; United States; Remote; USD 130,000 - 208,000; Full time

Benefits offered by this job

Growth opportunities

Wellness resources

Team-building events

Flexible time off

Recognition as a top workplace

Job summary

Ladders is recruiting an Account Executive, Enterprise to drive Chicago territory growth from a remote US-based location. You will build strategic account plans, engage C-level stakeholders, and steer complex deals from prospecting to contract signing.

The role balances outbound prospecting, account strategy, and deal execution while contributing to broader revenue objectives; a strong track record in enterprise software sales is required.

Qualifications

• 5+ years of enterprise sales in technology sectors.
• Proven track record engaging C-level executives.
• Expertise in strategic account planning and long sales cycles.
• Ability to navigate multi-stakeholder decision processes.
• Strong prospecting and territorial management skills.

Responsibilities

• Own and manage a robust sales pipeline for the Chicago territory.
• Develop and execute strategic account plans for enterprise customers.
• Build relationships with C-level executives to advance opportunities.
• Lead complex sales cycles from initial contact to contract.
• Acquire new business within the assigned territory.

Skills

Enterprise sales

C-level engagement

Strategic account planning

Complex multi-stakeholder sales

Pipeline management

Job description

For our client, we are seeking a Account Executive, Enterprise (Chicago) to join the team of a leader in the Information Technology space.

This role will focus on driving enterprise growth across the Chicago territory through strategic account development, new business acquisition, and disciplined pipeline management. The ideal candidate will partner closely with senior decision-makers to advance complex sales cycles and convert opportunities into long-term customer relationships. Success in this position will depend on strong territory execution, executive engagement, and the ability to navigate multi-stakeholder buying processes in a competitive technology market.

The role is well suited for a sales professional who can balance prospecting, account strategy, and deal execution while contributing to broader revenue objectives.

Location: Remote - US based candidates only, no visa sponsorship available

Compensation: $130,000 - $208,000 annually

Responsibilities

• Own and manage a robust sales pipeline for the Chicago territory
• Develop and execute strategic account plans for key enterprise customers
• Build and deepen relationships with C-level executives
• Lead complex sales cycles from initial contact through contract signing
• Acquire new business within the assigned territory by identifying and prospecting target accounts

Qualifications

• 5+ years of enterprise sales experience in technology sectors
• Proven track record of engaging C-level executives
• Strong understanding of comprehensive account strategy development
• Expertise in managing complex, multi-stakeholder sales processes
• Exceptional prospecting and territory management skills

Benefits

• Innovative and critical thinking environment
• Support for personal and professional growth
• Recognition as a top workplace in technology and workplace satisfaction
• Flexible time off and wellness resources
• Company-sponsored team-building events

Our client is an equal opportunity employer. We encourage you to apply even if you don't meet every qualification-your background could be exactly what this team needs.