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Business Development Lead Generator

Wintrust · Menomonee Falls, WI · $42,000–$55,000 a year · Full time

Posted Jul 23, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you had to reach people who didn't want to hear from you. How did you keep going?

What they are checking: Whether they can handle repeated rejection in an entry-level outreach role without losing energy.

Tell me about a goal you set for yourself and how you tracked progress toward it.

What they are checking: Whether they are self-directed with activity numbers in a role where daily effort is the main lever.

Where do you see this role taking you in a couple of years?

What they are checking: Whether they want to grow into sales or account work, which the posting frames as the path forward.

What would you do

TRICOM serves staffing agencies with payroll funding and back-office services. How would you figure out which agencies to call first?

What they are checking: Whether they can think about targeting and research instead of dialing through a list at random.

Give me the first thirty seconds of a cold call to a staffing agency owner.

What they are checking: Whether they can open with a relevant reason to talk rather than a generic pitch.

A prospect says they're happy with their current funding partner. What do you say?

What they are checking: Whether they can respect the answer, ask a useful question and leave the door open without being pushy.

About the work

What do you think a staffing agency owner worries about most when it comes to payroll and cash flow?

What they are checking: Whether they grasp the gap between paying temps weekly and collecting from clients later, which is what TRICOM solves.

How do you keep track of leads and follow-ups so nothing falls through the cracks?

What they are checking: Whether they would actually use a CRM consistently, since lead generation lives or dies on follow-up.

What makes a lead qualified enough to hand to a sales rep?

What they are checking: Whether they understand that passing weak leads wastes the sales team's time and hurts their own credibility.

How would you use LinkedIn, email and phone together to reach a hard-to-get decision maker?

What they are checking: Whether they know how to run a multi-touch outreach sequence rather than relying on one channel.

Practice this interview out loud.

Offer builds a real interview for this exact role at Wintrust from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

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The full job description

As published by Wintrust.

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. is a top provider of staffing administrative and financial services for employment agencies. We are seeking an enthusiastic professional to join our collaborative team as a Business Development/Lead Generator. In this entry-level 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: The Business Development Lead Generator 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. • Using a consultative approach, cold call and prospect new clients to generate interest and set appointments for account managers • Effectively utilize social media and other internet resources to attract and identify prospects for contact. • Build and manage prospect database, keeping accurate record and notes of contact information and prospect activity. • Follow-up with Sales staff on status of calls and sales funnel. Qualifications: • 1-2 years of experience in a sales position • Experience utilizing social media (Twitter, Instagram, Facebook, etc.) to prospect new clients and enhance sales • Detailed oriented to a document prospect calls in CRM database • Strong written and verbal communication skills • No travel required 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 $42,000-$55,000, 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.

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