Managing Director

Sinclair Broadcast Group•Cockeysville, MD

20h•$500,000 - $700,000•Onsite

About The Position

Sinclair Ventures is seeking an experienced private equity investor to lead its direct private equity activities and oversee its existing portfolio of non-media investments. The firm invests permanent capital in founder- and family-owned businesses and corporate carve-outs across the lower and middle market, with an emphasis on disciplined underwriting, attractive entry valuations, downside protection, and selective buy-and-build opportunities. The Managing Director will shape investment strategy, lead transactions from evaluation through closing, serve on portfolio company boards, and develop the investment team. Sinclair’s permanent-capital structure allows the firm to remain patient, walk away when price or structure is unattractive, and hold exceptional businesses for the long term. This position is based on-site at Sinclair’s Hunt Valley, Maryland headquarters.

Requirements

At least 12 years of direct private equity investing experience, including substantial responsibility for leading transactions, serving on portfolio company boards, and developing investment professionals.
A substantial attributed investment track record across the lower and middle market, demonstrating disciplined capital deployment, sound judgment through varied market cycles, and attractive risk-adjusted returns.
Demonstrated buy-and-build platform leadership in fragmented industries.
Strong judgment regarding valuation, downside risk, leverage, seller rollover, governance, management incentives, and capital structure.
Demonstrated willingness to decline or exit transactions when pricing or structural terms do not provide an appropriate margin of safety.
Meaningful portfolio company board experience, including acting decisively when performance falls below plan.
Exceptional integrity, communication skills, discretion, and an ownership mentality.
Bachelor’s degree required.

Nice To Haves

Experience within a committed-capital fund is strongly preferred.
M.B.A. or another relevant advanced degree preferred but not required.

Responsibilities

Set and refine Sinclair Ventures’ direct private equity strategy, investment criteria, sector priorities, and portfolio construction guidelines.
Develop selective consolidation theses in fragmented industries where a disciplined buy-and-build program can create platforms of scale.
Source and screen opportunities through broad relationships with investment bankers, advisors, lenders, and executives, as well as through marketed processes. Maintain constructive relationships when Sinclair is not the highest bidder, preserve the ability to re-engage if transaction circumstances change, and establish maximum purchase prices and required returns before significant diligence spending.
Lead structuring, negotiation, and execution end to end, including underwriting cases, purchase price, leverage, seller rollover, management equity, governance rights, and downside protections; direct all diligence workstreams and external advisors.
Present investment recommendations to Sinclair’s Investment Committee with clear, well-supported conviction, including explicit downside cases, key risks, and the conditions required to proceed.
Maintain the discipline to recommend walking away when valuation, structure, or risk-adjusted returns do not meet Sinclair Ventures’ standards.
Serve on portfolio company boards and establish clear governance, reporting, and accountability expectations.
Monitor performance against the underwriting case, identify deviations early, and drive corrective action, including leadership and succession decisions when necessary.
Lead add-on acquisition programs and partner with management teams on strategy, focused operating priorities, and capital allocation consistent with the original underwriting case.
Lead follow-on investment, recapitalization, financing, and exit decisions within defined ownership plans, and make the case for permanent ownership of exceptional platforms with the same rigor applied to the original underwriting.
Serve as a senior advisor to Sinclair’s CEO, Executive Vice Chairman, and Investment Committee.
Hire, mentor, and develop the next generation of Sinclair Ventures deal leaders, setting a culture of intellectual honesty, accountability, collaboration, and disciplined decision-making.
Strengthen screening, underwriting, diligence, investment committee, and portfolio-monitoring processes to an institutional standard.
Collaborate with Sinclair’s venture capital, asset management, and real estate teams on shared portfolio, governance, and capital-allocation matters.