Sales Associate Executive

Company: Wintrust Financial
Location: Waukesha
Posted on: October 30, 2025

Job Description:

Wintrust provides community and commercial banking, specialty finance and wealth management services through its 16 bank charters and nine non-bank businesses. Wintrust delivers the sophisticated solutions of a large bank while staying true to the relationship-focused, personalized service of our community banking roots. We serve clients in all 50 states with more than 200 branch banking locations in Illinois, southwestern Florida, northwestern Indiana, west Michigan and southern Wisconsin and commercial banking offices in Chicago, Denver, Milwaukee, Grand Rapids, Mich., and in key branch banking locations throughout Illinois. Our people are the heart of our business and we are proud to rank consistently as a top place to work. Wintrust is a $66 billion financial institution based in Rosemont, Illinois, and listed on the NASDAQ Global Select Market under the symbol “WTFC.” TRICOM Inc. of Milwaukee is a top provider of staffing administrative and financial services for privately held staffing companies. We are seeking an enthusiastic professional to join our collaborative team as a Sales Account Executive. In this role, you’ll have opportunities for growth and the ability to make a great impact on the organization. Why join us? An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 8 years) and Employee Recommended award by the Globe & Mail (past 6 years) Competitive hourly rate including additional commission pay Comprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement, to name a few Family-friendly work hours Promote from within culture What you’ll do: Position Overview: The Sales Associate is responsible for driving new client revenue through innovative lead generation, strategic outreach and a consultative sales approach. This individual will identify and engage prospective clients, uncover business needs, and bring in internal resources to guide advanced conversations and close new business. They will also play a key role in developing a robust sales funnel through creative strategy and targeted prospecting efforts. Sourcing new opportunities (Cold/Warm outreach): includes cold calls, emails, internet and social media research, trade show attendance, database mining, and outreach through industry partners to identify quality prospects Uncovering Prospect Needs/ Discovery calls: Engage in consultative and educational sales conversations to understand prospect pain points, business challenges and service gaps Strategy and Funnel Development: Collaborate with leadership to create targeted campaigns, identify high-opportunity prospects and brainstorm new approaches to pipeline growth Closing & Proposal Development: Advance qualified prospect opportunities by coordinating proposals and presentations in conjunction with internal leadership to increase win rates CRM/ Pipeline Management: Ensure timely and accurate tracking of all activity and opportunity stages within the CRM system Underwriting/ File Coordination: Support the processing of underwriting documentation for qualified prospects. Ensure detailed, organized information is provided to the underwriting team to present a clear picture of the opportunity. Deliver as much relevant data up front as possible to support a thorough and informed decision-making process for TRICOM. Qualifications: 5-7 years Inside/outside sales experience Associate’s degree or equivalent Strong written and verbal communication skills Advanced Computer skills 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 annual salary range for this role is $70,000-$80,000, 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. LI-Onsite 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.

Keywords: Wintrust Financial, Waukesha , Sales Associate Executive, Sales , Waukesha, Wisconsin