Alexander Eskra, Finance Expert in Milwaukee, WI, United States
Alexander Eskra

Finance Expert in Milwaukee, WI, United States

Member since July 3, 2020
Alexander is a licensed CPA with a decade of experience in financial services, including sales, mutual fund accounting and administration, regulatory compliance, and investment banking. His expertise includes financial analysis, valuation, and creating effective presentations. With a technical and creative skill set and a Booth MBA, Alexander helps businesses plan for growth and solve difficult problems through deep analysis and a thorough understanding of their challenges and opportunities.
Alexander is now available for hire


  • University of Chicago, Booth School of Business

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Case studies


  • Investment Banking Associate

    2019 - PRESENT
    CIBC Cleary Gull
    • Executed sell- and buy-side mergers and acquisitions for middle-market firms in the healthcare, manufacturing, business services, and software sectors.
    • Valued firms using discounted cash flow, leveraged buyout, and public company and comparable transaction analysis; analyzed client data and executed forecasts to demonstrate value propositions to potential buyers.
    • Drafted client presentations including confidential information memorandums, teasers, and management presentations.
    • Led business development activities such as creating marketing materials pitches to prospective clients.
    • Managed teams of attorneys, accountants, and lenders in the completion of interim milestones required to complete transactions.
    Focus areas: Mergers & Acquisitions (M&A)
  • Assistant Director

    2015 - 2019
    Northwestern Mutual
    • Assessed Northwestern's mutual funds, pension fund, and general account for investment risks in private equity, real estate, and public security portfolios, representing over $230 billion in assets.
    • Evaluated geopolitical, legislative, and reputational risk while serving as the foreign sanctions officer and made recommendations on investment decisions to the chief investment officer and chief risk officer.
    • Advised executive leadership and the board about regulatory risks and guided enterprise-level decisions, including a UK entity dissolution.
    • Authored and implemented new policies and procedures governing private securities investments within the EU.
    • Analyzed sub-adviser strategies and risks; guided selection, onboarding, and ongoing review for 17 external managers, representing over $27 billion in assets.
    Focus areas: Regulatory Compliance
  • Senior Specialist

    2011 - 2015
    Northwestern Mutual
    • Orchestrated Northwestern's most complex sub-adviser transition, integrating four fixed income sub-advisers in one day, completing the yearlong reorganization of the investment department, and reducing regulatory risk.
    • Led a project to comply with the Dodd-Frank Act, incorporating centrally cleared swaps within the accounting system and ensuring the accuracy of thousands of transactions per year.
    • Enhanced the monthly expense payment process for mutual funds, including automation of management and sub-advisory fee calculations, which remedied past calculation errors amounting to over $300,000.
    • Devised a process to automatically validate pricing and portfolio valuations, conserving over 150 person-hours per year.
    Focus areas: Accounting, Mutual Funds


  • MBA in Finance, Analytic Finance, Economics, and Strategic Management
    2016 - 2019
    University of Chicago, Booth School of Business - Chicago, IL, USA
  • Bachelor of Arts degree in Accounting
    2007 - 2011
    Cardinal Stritch University - Milwaukee, WI, USA


  • Certified Public Accountant
    SEPTEMBER 2012 - DECEMBER 2021
    Wisconsin Accounting Examining Board

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