Regional Sales Director (Chicago)

Ladders; United States; Remote; USD 113,000 - 143,000; Full time

Benefits offered by this job

Health insurance

Dental insurance

Vision insurance

Retirement plan

PTO

HSA

FSA

Life insurance

Disability insurance

Tuition reimbursement

Job summary

Ladders and our client are seeking a Regional Sales Director for the Chicago area with a remote work option. The role centers on driving territory growth, building a robust pipeline, and expanding broker and partner relationships to deliver consistent revenue.

Your responsibilities include guiding opportunities through the full sales cycle, delivering compelling presentations, and maintaining Salesforce activity to monitor territory performance.

Qualifications

• 3+ years of sales experience in B2B, SaaS, benefits, healthcare, or financial services.
• Proven track record of meeting or exceeding sales goals.
• Experience developing relationships with brokers, consultants, and partners.
• Strong presentation, negotiation, and communication skills.
• Ability to manage a geographic territory and travel schedule independently.
• Proficiency in Salesforce or similar CRM platforms.
• Strong organizational skills to prioritize multiple opportunities.

Responsibilities

• Own and execute a sales strategy for the assigned territory to achieve revenue goals.
• Develop and maintain a pipeline of qualified opportunities through networking and referrals.
• Identify and pursue high-value growth opportunities within the territory.
• Establish and maintain strong relationships with brokers, consultants, and key stakeholders.
• Schedule and conduct meetings to generate opportunities and advance sales cycles.
• Lead presentations and effectively communicate the value proposition to prospects.
• Maintain accurate Salesforce activity and manage territory performance.

Skills

Sales experience

Presentation skills

Negotiation

Communication

Organizational skills

Travel ability

CRM proficiency

Tools

Salesforce

Job description

For our client, we are seeking a Regional Sales Director (Chicago) to join the team of a leader in the Finance & Insurance space.

This remote opportunity is focused on driving territory growth through strategic outside sales execution. The role will build a strong pipeline, expand key relationships with brokers, consultants, and partners, and advance opportunities through every stage of the sales cycle. Success in this position will come from disciplined territory management, compelling presentations, and consistent revenue delivery across the assigned market.

Location: Remote

Compensation: $112,700 – $143,000 annually

Responsibilities

• Own and execute a sales strategy for the assigned territory to achieve revenue goals
• Develop and maintain a pipeline of qualified opportunities through networking and referrals
• Identify and pursue high-value growth opportunities within the territory
• Establish and maintain strong relationships with brokers, consultants, and key stakeholders
• Schedule and conduct meetings to generate opportunities and advance sales cycles
• Lead presentations and effectively communicate the value proposition to prospects
• Maintain accurate Salesforce activity and manage territory performance

Qualifications

• 3+ years of sales experience in B2B, SaaS, benefits, healthcare, or financial services
• Proven track record of meeting or exceeding sales goals
• Experience developing relationships with brokers, consultants, and partners
• Strong presentation, negotiation, and communication skills
• Ability to manage a geographic territory and travel schedule independently
• Proficiency in Salesforce or similar CRM platforms
• Strong organizational skills to prioritize multiple opportunities

Benefits

• Health, dental, and vision insurance
• Retirement savings plan
• Paid time off and health savings account
• Flexible spending accounts
• Life and disability insurance
• Tuition reimbursement

Our client is an equal opportunity employer.