Senior VC Associate @ Chaifetz Group in Chicago, IL

Chaifetz Group, LLC (“CG”) is a leading Chicago-based venture capital and private equity firm which partners with carefully selected entrepreneurs, business owners and management teams to build and grow game-changing businesses.

Anchored by the significant and permanent capital base of Dr. Richard Chaifetz, CG employs a flexible and long-term approach across a variety of investment strategies. For more information, visit 

Position Overview

The Senior Associate position with CG is a unique opportunity for candidates seeking a long-term and exciting career in venture capital and private equity. As a Senior Associate you will be highly visible, dealing with CG principals, portfolio companies and entrepreneurs on a daily basis. You will also develop a well-rounded and practical investment skill set by evaluating, executing and managing early- and later-stage venture capital and growth equity investments, as well as by being exposed to a direct and indirect private equity, real estate and public market transactions.

Primary day-to-day activities include:

  • Deal Due Diligence and Execution: Screening investment opportunities; meeting with entrepreneurs and management teams; conducting market research, financial and other due diligence; and preparing investment memoranda;
  • Sourcing New Investment Opportunities: Researching prospective investment targets; contacting entrepreneurs and business owners; maintaining relationships with qualified leads; and assessing the dynamics surrounding each potential opportunity;
  • Portfolio Company Support: Assisting existing CG portfolio companies with strategic operational initiatives and attending board and other key meetings; and
  • Community Development: Representing CG in a highly engaging and professional manner throughout the entrepreneurial and investing community, including networking and marketing functions.

The Senior Associate is expected to grow within the organization and will have the opportunity for meaningful long-term advancement.


The selected candidate will be expected to handle a high level of responsibility from the outset and must be motivated, hardworking, and comfortable in an unstructured setting that values initiative, creativity, maturity and poise.

Candidates should have outstanding interpersonal and analytical capabilities, and have the ability to dig deep into details, understand different business models and industries and assess the big picture.

At a minimum, candidates should have the following qualifications: 

  • 3+ years of professional experience;
  • Venture capital and/or private equity experience preferred; investment banking, strategy or consulting experience a plus;
  • Bachelor’s degree in business, finance, accounting, economics or other business related field;
  • MBA from top business school preferred;
  • Strong experience with Excel, including cash flow modeling and other investment valuation techniques;
  • Excellent communication skills. The successful candidate must be able to make frequent, concise, meaningful presentations about investment opportunities and cultivate important relationships and build contact networks;
  • Highly organized with an attention to detail;
  • Analytical acumen and excellent fact-driven judgement;
  • Advanced understanding of key finance and accounting concepts; and
  • Outstanding professional presentation with excellent verbal and written communication skills.

If interested, please apply here.

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