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Wintrust

Community banking, wealth management, lending

Executive Assistant

Full-Time
$27 - $39.50/hr+ Annual bonus
Mid
Rosemont, IL, USA
In Person

About the job

Requirements
  • Three to five years of relevant experience.
  • Experience recognizing the necessity of adhering to pre-established timetables without compromising quality.
  • Ability to anticipate leadership needs by proactively managing complex calendars.
  • Ability to manage seamless logistics for meetings and presentations, including booking venues and preparing materials.
  • High proficiency in Microsoft Office Suite.
  • A background in the financial or insurance industry is a plus.
  • High personal integrity to build and maintain trust across senior leadership, internal teams, and external partners.
Responsibilities
  • Manage the daily schedule and travel of the Chief Executive Officer, President, and Chief Operating Officer.
  • Schedule and organize travel itineraries and arrangements, including airline, hotel, and car services, and assist with expense reports.
  • Set up and coordinate meetings, work with vendors on external venues, and coordinate catering and meals.
  • Track monthly executive meetings, send reminders to team members, and create agenda decks by collecting and consolidating updates from executives.
  • Track and schedule special events, provide meeting resources, and create name tags for executives and team members.
  • Track meetings, set agendas, gather information, assimilate decks, and design announcement slides for company meetings.
  • Support projects for the Managing Sales Directors.
  • Provide administrative support, including filing, copying, and typing correspondence, presentations, and spreadsheets.
  • Manage business-related arrangements, including personal travel, car services, flight reservations, and restaurant reservations.
  • Generate and share reports.
  • Coordinate visits for outside guests or candidates.
  • Complete other assigned tasks.
Desired Qualifications
  • Background in the financial or insurance industry.

About the company

Wintrust provides a suite of financial services including community banking, wealth management, commercial banking, and mortgage lending across more than 175 locations. The company operates by collecting deposits and providing loans to individuals and businesses, generating revenue through interest income and service fees. Unlike many large national banks, Wintrust maintains a local community banking model that focuses on personal relationships within specific geographic regions like the Chicago metropolitan area. Its goal is to serve as a one-stop financial resource for individuals, small-to-mid-sized businesses, and institutional clients.

Company Size

1,001-5,000

Company Stage

IPO

Headquarters

Rosemont, Illinois

Founded

1995

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Simplify's Take

What believers are saying

  • Q2 2026 net income reached $233.7 million, extending the company’s record streak.
  • Deposits rose $2.2 billion and loans rose $1.6 billion in Q2 2026 without higher deposit costs.
  • Management targets mid- to high-single-digit loan and deposit growth, with another branch buildout in 2026.

What critics are saying

  • Net interest margin fell to 3.50% in Q2 2026 as loan yields dropped.
  • Noninterest-bearing deposits declined $316 million in Q2 2026 while CDs and money markets grew.
  • A Chicago commercial-real-estate downturn or deposit war can crush returns and freeze expansion by 2027.

What makes Wintrust unique

  • Wintrust reached third in Chicago deposit market share by 2025.
  • Management delivered six straight record net-income quarters through Q2 2026 using organic growth only.
  • Its franchise mixes community banking, premium finance, wealth management, and mortgage lending across Midwest markets.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

Disability Insurance

401(k) Retirement Plan

401(k) Company Match

Parental Leave

Employee Assistance Program (EAP)

Flexible Spending Account (FSA)

Employee Stock Purchase Plan

Transportation and Commuting Benefits

Pet Insurance

Growth & Insights and Company News

Headcount

6 month growth

↑ 16%

1 year growth

↑ 16%

2 year growth

↑ 16%
Yahoo Finance
Aug 13th, 2026
Wintrust Financial reports record Q2 net income with $739.5M revenue, up 9.9% year-on-year

Wintrust Financial reported second-quarter revenues of $739.5 million, up 9.9% year on year, meeting analysts' expectations. However, the company slightly missed net interest income estimates whilst narrowly beating earnings per share forecasts. The Chicago-area regional bank, which operates community banks and provides specialty finance services including insurance premium financing and wealth management, achieved its sixth consecutive quarter of record net income. Chief executive Timothy Crane highlighted "strong diversified loan growth funded by robust organic deposit growth" as evidence of the company's business model strength. Despite the record results, Wintrust's shares fell 2.7% following the announcement, trading at $159.22. The stock was amongst 93 regional banks tracked, which collectively reported mixed second-quarter results with revenues meeting consensus estimates.

Yahoo Finance
Jul 21st, 2026
Wintrust Financial posts Q2 revenue of $739M, beats EPS estimates by 4.7%

Wintrust Financial met Wall Street's revenue expectations in Q2 2026, reporting sales of $738.6 million, up 9.8% year on year. The regional banking company's non-GAAP profit of $3.30 per share beat analysts' consensus estimates by 4.7%. The quarter marked Wintrust Financial's sixth consecutive quarter of record net income. Net interest income reached $597.4 million, showing 9.3% year-on-year growth, though it slightly missed analyst estimates of $603.9 million. Chief Executive Officer Timothy S. Crane highlighted strong diversified loan growth funded by robust organic deposit growth. Founded in 1991 as a community-focused alternative to big banks in the Chicago area, Wintrust Financial has achieved an 11% compounded annual revenue growth rate over the past five years.

Yahoo Finance
Apr 27th, 2026
Wintrust Financial beats Q1 estimates with $715.8M revenue on organic loan growth

Wintrust Financial reported first-quarter results featuring robust loan and deposit growth, stable net interest margin and disciplined expense management. Revenue reached $715.8 million, beating analyst estimates of $707.2 million, whilst adjusted earnings per share of $3.22 exceeded expectations of $2.96. CEO Timothy Crane emphasised that "all of our growth is organic", highlighting momentum from existing business lines. Credit quality metrics remained stable, with low levels of nonperforming assets and charge-offs. The company's exposure to commercial real estate and speciality finance remains well diversified and monitored. During the earnings call, analysts questioned loan growth timing, premium finance outlook, deposit sustainability and wealth management revenue. Management indicated confident expectations for continued customer acquisition and stable competitive dynamics in core markets, though wealth management revenue should normalise in coming quarters.

Yahoo Finance
Apr 21st, 2026
Wintrust Financial beats Q1 estimates with $715.8M revenue, expects strong loan growth in Q2

Wintrust Financial reported Q1 revenue of $715.8 million, beating analyst estimates of $707.2 million with 11.4% year-on-year growth. Non-GAAP earnings per share of $3.22 exceeded consensus by 8.7%. The regional bank's results were driven by organic loan and deposit growth, with deposits up $1.2 billion and loans up $1 billion on an annualised basis. Net interest margin remained stable at 3.56%, whilst wealth management and operating lease income boosted noninterest revenue. Credit quality metrics stayed strong, with nonperforming assets and charge-offs at low levels. CEO Timothy Crane stated the company expects "solid net interest income growth in the coming quarters", projecting particularly strong loan growth in Q2 from property and casualty premium finance. Management plans to maintain net interest margin near 3.5% whilst investing in digital capabilities.

Yahoo Finance
Apr 19th, 2026
Wintrust Financial to report Q1 earnings Monday, revenue expected up 10% year-on-year

Wintrust Financial will report first-quarter earnings on Monday after market close. The regional banking company beat revenue expectations last quarter, reporting $715.6 million, up 11% year on year. Analysts expect revenue to grow 10% year on year this quarter, improving from 6% growth in the same period last year. However, analysts have largely reconfirmed their estimates over the past 30 days, and Wintrust has missed Wall Street's revenue estimates multiple times over the last two years. Peers BancFirst and KeyCorp recently reported revenue growth of 7.8% and 10.2% respectively, both beating estimates. Regional bank stocks have risen 12% on average over the past month, whilst Wintrust is up 11.7%. Analysts have set an average price target of $168.25, compared to the current share price of $148.09.