Vice President

Sinclair Broadcast Group•Cockeysville, MD

2h•$200,000 - $270,000•Onsite

About The Position

Sinclair Ventures is seeking an experienced Vice President to join its investment team. Sinclair Ventures manages approximately $1.0 billion of non-media investments across private equity, venture capital, and real estate and applies a disciplined buy-and-build approach to the lower and middle market. The Vice President will focus primarily on direct private equity investments in founder- and owner-operated businesses and corporate carve-outs, with responsibility spanning opportunity screening, underwriting, transaction execution, and post-close oversight. Sinclair invests permanent capital through a patient and highly selective strategy emphasizing attractive entry valuations, downside protection, disciplined structuring, and the willingness to walk away when price or terms do not provide an appropriate margin of safety. The role will also support monitoring of the venture capital and real estate holdings.

Requirements

Approximately 7-12 years of relevant experience, including significant direct private equity transaction experience; prior investment banking or transaction advisory experience may be considered as part of that background.
Demonstrated leadership of material portions of a transaction process — not solely analytical support.
A supportable attributed investment track record on transactions where you played a meaningful role, including the ability to discuss both successful and underperforming investments.
Expert-level Excel financial modeling, alongside strong valuation, accounting, written communication, and presentation skills.
Disciplined judgment regarding valuation, capital structure, and downside protection, with the ability to distinguish an attractive company from an attractive investment.
High integrity, ownership, accountability, and discretion.
Bachelor’s degree required

Nice To Haves

M.B.A. preferred but not required

Responsibilities

Screen a broad pipeline of marketed opportunities, with an emphasis on founder-owned businesses, corporate carve-outs, and selective consolidation opportunities in fragmented industries; cultivate the banker, advisor, lender, and executive relationships that support broad market coverage.
Develop evidence-based investment theses, evaluate normalized earnings and sustainable free cash flow, and establish disciplined valuation parameters and maximum purchase prices before significant diligence spending.
Identify advantaged entry points created by transaction dynamics, seller objectives, or process disruption; preserve constructive relationships when Sinclair is not the highest bidder and maintain readiness to re-engage if circumstances change.
Own the financial model, including valuation, capital structure, and base, upside, and downside cases; clearly identify the assumptions that drive returns and capital risk.
Evaluate leverage, seller rollover, management equity, governance rights, and other structural protections; manage diligence workstreams and coordinate third-party advisors, financing sources, and internal stakeholders.
Prepare and present investment committee materials; support negotiation of letters of intent, purchase agreements, and financing arrangements.
Maintain strict discipline on broken-deal costs, defer significant external spending until price and structure justify the investment, and help Sinclair move decisively when a process creates a preferential opportunity.
Partner with portfolio company management teams on focused strategic priorities, operating plans, performance metrics, and capital allocation; participate in board meetings and governance processes.
Monitor results against the underwriting case, flag emerging risks early, and recommend corrective action.
Support add-on acquisitions, targeted operating improvements, management recruitment, follow-on investments, financing alternatives, and exit or long-term hold decisions consistent with the original underwriting case.
Support oversight of the venture capital and real estate holdings alongside external managers and operating partners.
Mentor Associates, Analysts, and MBA interns.
Strengthen screening, underwriting, investment committee, and portfolio-monitoring processes, using data, analytics, and AI-enabled tools to improve efficiency.
Serve as a trusted investment partner to the Managing Director and other senior leaders.