Vice President, Sightway Capital

New York, New York, United States

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Sightway Capital is a Two Sigma company focused on private equity investments. We have developed expertise in building business platforms in asset-intensive businesses across several industries including financial services, natural resources, and transportation. We endeavor to combine differentiated investment strategies, world class management teams with deep expertise in these sectors, and the integration of Two Sigma data science, technology, analytics, and corporate platform benefits into our portfolio. As part of this strategy, Sightway employs a flexible and creative approach with respect to investment type, structure, duration, and investment entry and exit strategies. The Sightway team typically plays an active role in each investment, working closely with the management team and other key constituents to develop value creation opportunities such as add-on acquisitions and efficient capital markets execution. We have a growing team of 40+ professionals with significant institutional private investment experience that have made investments totaling in excess of $2Bn.

Two Sigma Investments is an alternative asset management firm which manages capital on behalf of third party investors and manages approximately $58 billion across world markets. Two Sigma Investments was founded in 2001 employs over 1600 professionals with offices in New York, Houston, London and Hong Kong.


Sightway Capital seeks to recruit a Vice President to join its investment team to pursue private markets investment activities in its targeted sectors across financial services and real assets. 

In this role, the Vice President will work with the team in all aspects of the investment process, including deal sourcing, evaluation, structuring, negotiation and financing, as well as monitoring new and existing portfolio investments.  The Vice President will organize and manage many aspects of an investment process, including managing internal and external stakeholders’ expectations and deliverables, getting everyone to work toward a common objective and, after deal execution, handling on-going portfolio management.  The Vice President will also help to manage and coach associate team members to enable them to grow and take on greater responsibilities with less oversight over time.


  • 5+ years of principal investing experience, ideally at a control-oriented private equity firm
  • A demonstrated track record of private equity investments in the Financial Services or Real Assets sector
  • A demonstrated track record of successfully underwriting and overseeing the execution of complex, structured investments
  • Personality, mindset, and investment approach that fits well with an entrepreneurial, growing firm
  • Ability to deeply and thoroughly analyze and dissect a business; i.e. understanding the components and drivers of success beyond financial statements
  • Presence and self-confidence to interface with the key constituents of the firm including management teams of companies, deal sources, co-investors, and service providers among others
  • A pattern of excellence, both personally and professionally, demonstrated by the individual’s education, career track record, intellect, and professional reputation
  • Excellent verbal and written communication and presentation skills, as well as the ability to interact effectively with management teams
  • Extraordinarily strong quantitative analytical skills
  • Self-awareness, maturity, and irreproachable integrity


An undergraduate degree is required; an advanced degree such as an MBA or a JD can be a plus.