As the largest life insurance premium finance company in the country, Wintrust Life Finance provides customized financing solutions to qualified borrowers seeking to finance their life insurance premiums. Our financing solutions have supported numerous planning structures, including traditional wealth transfer, key-man insurance, buy-sell arrangements, split dollar arrangements, term alternatives, charitable giving, income replacement strategies, and more. Wintrust Life Finance is a subsidiary of Wintrust, a financial services company with more than $66 billion in assets.

Why join us?

• An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 10 years) and Employee Recommended award by the Globe & Mail (past 6 years)

• Competitive pay and discretionary or incentive bonus eligible

• Comprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a few

• Promote from within culture

Why join this team?

• This position has the opportunity to interface with and have a positive impact on multiple areas of Wintrust's business
• We hold ourselves accountable to high standards, share wins, operate ethically, and have fun

 Position Summary:

This role is the operational engine behind the Chief Growth Officer/Head of Sales and regional VPs — a hybrid internal wholesaler, sales support strategist, and marketing operator who strengthens advisor relationships, drives pipeline momentum, and elevates the unit’s brand presence.

The candidate is a core member of the WLF client facing team. This individual partners directly with the Head of Sales and supports RVPs by managing advisor engagement, coordinating/supporting pipeline activity, producing marketing collateral, and ensuring the sales organization runs with precision.

This role blends relationship management, pipeline orchestration, content creation, and sales enablement — ideal for someone who thrives in a fast moving, advisor facing environment and understands the nuances of life insurance, premium finance, HNW/UHNW client services.

Essential Responsibilities:

Sales Enablement

• Serve as the primary internal point of contact for our Head of Sales, RVPs, their advisors/clients, and other centers of influence.
• Support regional VPs with meeting prep, follow‑ups, on-site conference/tradeshow support, and proposal coordination with ‘new business.’
• Manage inbound advisor inquiries and triage requests to underwrite, operations, or regional leadership.
• Maintain visibility into pipeline stages, benchmarks/goals, and business calendar milestones.
• Liaise with relevant business units and product partners where appropriate.

Internal Wholesaling

• Conduct proactive outreach to advisor partners to drive meeting activity and uncover new opportunities.
• Schedule and prepare meetings, webinars, and training sessions for regional VPs.
• Deliver product overviews, premium finance fundamentals, and lending solution positioning to newer, less seasoned advisors.
• Track advisor engagement metrics and identify high‑potential relationships.

Marketing & Content Development

• In collaboration with WTFC marketing account manager, create polished marketing materials: pitch decks, one‑pagers, case studies, and advisor‑facing collateral.
• Partner with the Head of Sales to refine messaging, brand tone, and strategic communication.
• Manage digital content updates (website, advisor portal, email campaigns) in concert with WTFC marketing
• Support event planning, conference prep, and roadshows in concert with WTFC events/marketing

Pipeline & CRM Management

• Maintain CRM accuracy across leads, opportunities, and advisor interactions.
• Generate weekly pipeline reports for the Head of Sales and regional VPs.
• Monitor production trends, advisor activity, and territory performance.

Qualifications:

• 3–7 years of experience in financial services, ideally in premium finance, insurance distribution, private client lending, or RIA/wealth management channels.
• Strong understanding of advisor ecosystems, and sales cycles
• Exceptional communication skills — polished, concise, and executive ready.
• Proficiency with CRM systems, pipeline reporting, and sales analytics.
• Ability to produce clean, modern marketing materials and presentations.

Benefits

Medical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet Insurance 

Compensation

The estimated salary range for this role is $85,000 - $110,000, along with eligibility to earn an annual bonus. Actual salaries may vary based on several factors, such as a candidate’s qualifications, skills and experience.

From our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life.  To build a company that reflects the communities we serve, we believe that fostering a unique and inclusive workplace where everyone feels valued and empowered to succeed will support our ongoing success.  Wintrust Financial Corporation, including community banking and financial services subsidiaries, is an Equal Opportunity Employer.  All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, disability, veteran status, genetic information, and other legally protected categories.