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Portfolio Manager II, Community Development

Wintrust Open
Chicago Full-time Manager Investment & Corporate Development

At a glance

Manager-level Investment & Corporate Development role at Wintrust. Chicago · full-time · $85,000–$110,000 base.

SalaryStated by Wintrust
$85,000 – $110,000
Base salary for this role, in USD per year, as published in the posting.
This role, from WintrustOur estimate for the market: $94,375–$156,575Median $123,750
Below the market median of $123,750 for mid-level investment & corporate development roles in Chicago.
Worked out from 44 postings that stated pay, median $123,750. Last updated Nov 12, 2026.
RoleInvestment & Corporate Development
SeniorityManager
LocationChicago
EmploymentFull-time
Base pay$85,000–$110,000
PostedNov 4, 2026
Role brief

financeroles summary, based on the employer's posting.

What you'll do

  • Assess community development investments, including LIHTC funds, NMTC deals, CDFI lending and SBIC funds
  • Examine sponsors, fund managers and underlying assets to judge financial strength, credit exposure and investment risks
  • Build approval packages that explain deal structure, sponsor credentials, financial results, CRA effects and your recommendation
  • Track existing investments through annual reviews, risk ratings, covenant checks and asset performance monitoring
  • Review partnership, fund and closing documents with internal and external partners for alignment with approvals

What you bring

  • At least three years in commercial real estate credit, investment underwriting, tax credit finance or another listed field
  • Working familiarity with LIHTC, NMTC, CDFIs or affordable housing finance
  • A bachelor's degree, preferably in business, finance, accounting or economics

Who this fits

This role suits you if you can handle detailed credit analysis, financial writing and several transactions alongside ongoing portfolio work. You'll work with deal teams, clients, counsel and senior leaders. The role is based in Chicago.

From the employer

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.”


Why join us?

  • An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 12 years) and Employee Recommended award by the Globe & Mail (past 6 years)
  • Competitive pay and annual discretionary bonus eligible
  • Comprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company matches and tuition reimbursement to name a few
  • Family-friendly work hours
  • Promote from within culture

Portfolio Manager II – Community Development

The Portfolio Manager II, Community Development will support the ongoing portfolio management of the Bank's community development investment platform, including Low-Income Housing Tax Credit (LIHTC) investments, New Markets Tax Credit (NMTC) investments, Community Development Financial Institution (CDFI) and equity-equivalent (EQ2s) investments, Small Business Investment Company (SBIC) funds, and other CRA-eligible investments.

This position offers the opportunity to play a central role in advancing the Bank's community development strategy while supporting investments that create affordable housing, drive economic development, and deliver meaningful community impact.

What You'll Do

  • Underwrite and analyze community development investment opportunities, including LIHTC multi-investor funds, direct NMTC investments, CDFI loan pools, EQ2 investments, SBIC funds, and other mission-driven investments.
  • Perform detailed financial, credit, and risk analysis of fund managers, syndicators, developers, sponsors, and underlying assets to assess investment viability and identify key risks.
  • Independently prepare comprehensive investment opportunity and credit approval packages that clearly articulate transaction structure, sponsor qualifications, financial performance, investment risks, CRA impact, and recommendation rationale.
  • Independently analyze credit and financial information of property and individuals to determine the degree of risk associated with the extension of credit.
  • Complete annual reviews, portfolio monitoring reports, risk rating assessments, and covenant compliance analyses for existing investments.
  • Oversee documentation and ongoing monitoring of asset and client performance.
  • Work with external and internal business partners on the review of partnership agreements, operating agreements, subscription documents, fund documents, legal opinions, and other transaction-related closing documentation
  • Review credit approval memorandums and attorney-prepared closing documents for new and renewed investments to ensure compliance and adherence to the approval guidelines.
  • Interact with lending and investment staff, deal teams and clients in a welcoming and professional manner.

Qualifications

  • Bachelor's degree (Business, Finance, Accounting, or Economics preferred).
  • Strong understanding of general credit and risk principles, and banking policies/procedures; formal bank credit training preferred.
  • Minimum 3 years of experience in commercial real estate credit, investment underwriting, tax credit finance, or community development finance.
  • Working knowledge of Low-Income Housing Tax Credits (LIHTC), New Markets Tax Credits (NMTC), CDFIs, or affordable housing finance.
  • Strong analytical and business writing skills
  • Strong organizational skills with the ability to manage multiple transactions and portfolio responsibilities simultaneously.
  • Good interpersonal skills with internal partners, counsel, clients and senior management.
  • Accounting and finance knowledge, as well as knowledge of real estate fundamentals and concepts.

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.

Opportunity

Investment & Corporate Development work from LinkedIn, X, Reddit and Upwork, in one list.

Each morning you get everything that fits, strongest first.

Investment & Corporate Development$80k+

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By the team behind financeroles.

Find me work
Opportunity

Investment & Corporate Development work from LinkedIn, X, Reddit and Upwork, in one list.

Each morning you get everything that fits, strongest first.

Find me work

By the team behind financeroles.