Director of Sales

Pursuit; Chicago (IL); On-site; USD 120,000 - 190,000; Full time

Benefits offered by this job

Car allowance

Fuel expenses covered

Health benefits

401(k) with match

Paid vacation

Laptop and expense card

Job summary

Pursuit is seeking a Regional Director of Sales to drive revenue growth across the Upper Midwest. The role emphasizes consultative selling, strategic account expansion, and leadership within a private equity-backed fleet solutions provider.

You will manage complex sales cycles, engage with senior executives, and travel extensively to meet clients, delivering value-driven solutions and closing strategic deals.

Qualifications

• 5+ years of proven B2B sales experience.
• Experience managing complex sales cycles and selling solutions.
• Experience in engaging with senior-level executives and multiple decision-makers.

Responsibilities

• Develop and execute strategic sales plans to drive revenue growth across the Upper Midwest territory.
• Prospect and develop new business opportunities while growing existing accounts.
• Manage complex, consultative sales cycles with multiple stakeholders including C-suite.
• Build relationships with municipal organizations, commercial fleet operators, and other B2B customers.
• Identify customer challenges and present value-based solutions.
• Manage territory activity, pipeline development, forecasting, and CRM reporting.
• Collaborate with leadership to identify growth opportunities and travel to meet clients.

Skills

B2B sales

Complex sales cycles

Executive engagement

Market development

Independent工作

Education

Bachelor's degree preferred

Job description

Pursuit is partnered with a rapidly growing, private equity-backed leader in commercial fleet solutions that is looking to add a Regional Director of Sales to its team! With over 20 years of success, consistent year-over-year growth, and an aggressive expansion strategy, this is an exciting opportunity to join a well-established organization with significant growth potential.

Our client is looking for a highly motivated, entrepreneurial sales professional who thrives in a consultative, relationship-driven sales environment. This individual will be responsible for developing new business, expanding existing accounts, and driving revenue growth throughout the Upper Midwest territory.

Responsibilities

• Develop and execute strategic sales plans to drive revenue growth across the assigned territory.
• Prospect and develop new business opportunities while growing existing customer relationships.
• Manage complex, consultative sales cycles involving multiple stakeholders and C-suite decision-makers.
• Build strong relationships with municipal organizations, commercial fleet operators, and other B2B customers.
• Identify customer challenges and present customized, value-based solutions.
• Manage territory activity, pipeline development, forecasting, and CRM reporting.
• Collaborate with internal leadership to identify opportunities for continued market expansion.
• Travel throughout the territory to meet with customers and prospects.

Qualifications

• 5+ years of proven B2B sales experience with a strong track record of success.
• Experience managing complex sales cycles and selling solutions rather than transactional products.
• Proven ability to prospect, develop new markets, and grow existing accounts.
• Strong communication, presentation, and relationship-building skills.
• Self-motivated, entrepreneurial mindset with the ability to work independently.
• Experience selling to senior-level executives and multiple decision-makers.
• Experience in fleet management, rental/leasing, transportation, refuse/recycling, or municipal sales is a plus.
• Bachelor's degree preferred.
• Must be comfortable with 50%+ overnight travel.
• Strong Six-Figure Base Salary + Performance Bonuses ($180K+ OTE)
• Additional bonus potential for exceeding performance targets
• $800/month car allowance + company-paid fuel expenses
• Excellent health benefits with employee coverage paid by the company
• 401(k) with up to 4% company match
• Paid vacation
• Company-provided laptop, iPhone, and expense card
• Strong leadership team with opportunities for long-term career growth