Director of Strategic Financing & Cash Optimization

AHEAD; Chicago (IL); On-site; USD 180,000 - 260,000; Full time

Benefits offered by this job

Medical, Dental, and Vision Insurance

401(k)

Paid company holidays

Paid time off

Parental and caregiver leave

Job summary

AHEAD is seeking a Director, Financial Solutions to lead strategic financing initiatives within our Financial Solutions Group. This role partners with sales leadership, clients, and internal finance teams to structure solutions that improve cash outcomes and enable complex transactions.

The ideal candidate combines deep financial-selling experience with commercial judgment, analytical rigor, and the ability to communicate effectively with internal and external stakeholders across the business.

Qualifications

• 10+ years of experience in financial selling.
• Bachelor's degree in Accounting, Finance, Business, or related field.
• MBA preferred.
• Experience with Salesforce and MS Office suite.

Responsibilities

• Attend quarterly business review (QBR) meetings with sales leadership.
• Lead financial selling for product opportunities, including TCO analysis.
• Respond to financing requests with strategic solutions.
• Provide tax and freight billing instructions for financed opportunities.
• Resolve terms mismatches using internal criteria.
• Manage unfunded report to minimize DSO for financed receivables.
• Model and present Dell TLA opportunities to positions AHEAD with clients.
• Build trusted relationships with sales teams and partners as a financing SME.

Skills

Financial selling

Analytical thinking

Communication skills

Collaboration across departments

Commercial mindset

Presentation skills

Problem solving

Education

Bachelor's degree in Accounting, Finance, Business, or related field

MBA

Tools

Salesforce

Microsoft Excel

Microsoft PowerPoint

Job description

AHEAD is seeking a Director, Financial Solutions to lead strategic financing initiatives within our Financial Solutions Group. This role partners with sales leadership, clients, and internal finance teams to structure solutions that improve cash outcomes and enable complex transactions.

The ideal candidate combines deep financial-selling experience with commercial judgment, analytical rigor, and the ability to communicate effectively with internal and external stakeholders across the business.