W

Wintrust

Community banking and wealth management provider

Vice President Business Strategy

Full-TimeUpdated on 10/20/2026
$98k - $132k+ Annual Bonus
Expert
Bachelor's, MBA
Rosemont, IL, USA
In Person
Business & StrategyCorporate Strategy

About the job

Requirements
  • 10-15 years of experience in the financial industry.
  • Experience owning a strategic initiative from concept to completion.
  • A bachelor's degree is required.
Responsibilities
  • Manage WLF's process efficiency and strategy administration team.
  • Collect and analyze premium finance data related to the strategic plan and generate insights to initiate strategic development activities.
  • Complete regularly scheduled market research in support of the strategic plan.
  • Collaborate with departments to evaluate operations and identify growth and development opportunities.
  • Monitor and evaluate the performance of the company's strategies, initiatives, and objectives, and report findings to executive leaders.
  • Help drive decision-making resulting in medium- and long-term process improvements.
  • Present business findings and projections proactively, and make recommendations to the department EVP and other leaders as appropriate.
  • Support the EVP in developing and communicating WLF's strategic initiatives, including presentations, financial reports, and models in written and verbal formats.
  • Lead effective, efficient meetings with clients, prospects, and WLF's Strategic Initiative Owners to drive strategic plan efforts.
  • Work with the department EVP and project managers to ensure internal resources are collaborative and projects and work streams are on time and aligned with expectations.
  • Partner with WLF's Strategic Initiative Owners, Wintrust's ePMO, and Wintrust Oversight teams to drive strategic-level project approval and implementation.
  • Drive internal understanding of key customer personas and engage with clients and prospects to better understand workflows; synthesize learnings for internal stakeholders to facilitate loan growth.
  • Partner with Sales, Sales Leadership, and Client Success teams to define, enhance, track, and drive product adoption.
  • Build product-level KPIs through the lens of the Strategic Plan to define, monitor, and manage success.
  • Support optimization modeling and process planning with team-level management, outside sales, and internal stakeholders; evaluate premium tiers, calculate quote conversion ratios, average down payments, installments, and price to provide actionable recommendations for growth opportunities.
  • Identify opportunities and gaps, and scale efficiencies and new ways of working across multiple projects and environments.
  • Influence and facilitate long-term relationships with other departments and vendors.
  • Source data to make compelling, tangible recommendations for a future state for the organization.
  • Leverage relationships and organizational values to prioritize outcomes effectively.
  • Employ practical methods and action steps to move the organization toward the strategic vision.
  • Identify obstacles to transformation and challenge conventional thinking.
Desired Qualifications
  • Premium finance experience is preferred.
  • An MBA is preferred.

About the company

Wintrust Financial coordinates a network of community and commercial banks that provide banking, wealth management, insurance premium financing, mortgage origination, and related financial services across 175+ locations in Chicagoland, NW Indiana, southern Wisconsin, and Florida. Customers access products through checking and savings accounts, loans and lines of credit, and cash management, with wealth management offering advisory services and planning, premium financing enabling payment of insurance premiums over time, and mortgage origination helping clients secure home loans. The company differentiates itself by offering a broad, locally focused set of services across a wide regional footprint, tailored to community needs through its multiple divisions. Its goal is to deliver accessible, comprehensive financial solutions to individuals and businesses while expanding its network of community banks and services.

Company Size

1,001-5,000

Company Stage

IPO

Headquarters

Rosemont, Illinois

Founded

1995

Get referred to Wintrust

See people who can refer or advise you

Simplify Jobs

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.

Help us improve and share your feedback! Did you find this helpful?

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

Company News

Yahoo Finance
Oct 20th, 2026
Wintrust, Alphabet and Amazon screen as undervalued, trading up to 45% below fair value

Simply Wall St has flagged three stocks that screen as undervalued on future cash flows, trading up to 45% below fair value: Wintrust Financial, Alphabet, and Amazon.com. The screener surfaces 474 more companies with similar cash flow and valuation gaps. Wintrust Financial, a Chicago-based regional bank, is valued at about $9.6 billion. Its Community Banking arm brings in about $2.1 billion in revenue, Specialty Finance about $538 million, and Wealth Management about $214 million. Alphabet is valued at about $4,145.1 billion. Google Services generates about $367.1 billion in revenue and Google Cloud about $77.6 billion. Amazon.com is valued at about $2.7 trillion. North America brings in about $453.7 billion, International about $173.6 billion, and AWS about $148.4 billion.

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.