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.

The Investor We Are Looking For

This search is defined by demonstrated capability, judgment, and leadership rather than pedigree alone.

· Institutional investing discipline. You operate in a rigorous private equity environment with a formal investment committee, disciplined underwriting standards, and clear performance accountability. Experience within a committed-capital fund is strongly preferred.

· A substantial attributed investment track record in the lower and middle market, including founder- and family-owned businesses and corporate carve-outs, with clear attribution as a deal captain across the investment lifecycle.

· Demonstrated attractive risk-adjusted returns, supportable deal by deal in diligence, including a candid assessment of losses and lessons learned.

· Buy-and-build expertise in fragmented industries, including underwriting platforms, pricing add-ons with discipline, and integrating businesses without destroying what made them attractive.

· High strategic IQ with in-the-weeds command of detail. You can frame an industry thesis and, in the same meeting, interrogate a quality-of-earnings adjustment or working-capital peg line by line.

· Quick, decisive judgment. You kill deals early when they fail established parameters, commit quickly when a broken process or shifting seller dynamic creates an advantaged entry, and control broken-deal costs through timely decisions.

· True leadership and talent development, with a record of hiring, mentoring, and promoting investment professionals who have progressed into deal leadership roles.

· Senior market relationships. Established relationships with investment bankers, lenders, advisors, executives, and operating professionals, with the credibility to maintain broad market coverage, access high-quality marketed opportunities, and mobilize the right financing and operating resources when needed. The role requires trusted relationships and disciplined coverage, not a mandate to build a proprietary sourcing organization.

· Credibility with capital providers and co-investors, including the ability to attract financing and, where strategically appropriate, third-party capital alongside Sinclair’s balance sheet.

Key Responsibilities

Investment Leadership

· 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.

Portfolio Governance

· 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.

Leadership and Firm Building

· 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.

Qualifications

· 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; M.B.A. or another relevant advanced degree preferred but not required.

Compensation and Benefits

The base salary range for this role is $500,000 to $700,000. The position is also eligible for a performance-based annual bonus and participation in a long-term investment incentive program tied to the performance of qualifying investments. Final compensation will reflect the candidate’s track record, leadership capability, and alignment with Sinclair Ventures’ strategy. Full time positions are eligible for benefits that include participation in a retirement plan, life and disability insurance, health, dental and vision plans, flexible spending accounts, 15 paid vacation days, 2 paid personal days, 9 paid holidays, 40 hours of paid sick leave, parental leave, and employee stock purchase plan.

Sinclair is proud to be an equal opportunity employer and a drug free workplace. Employment practices will not be influenced or affected by virtue of an applicant's or employee's race, color, religion, sex (including pregnancy, gender identity, and sexual orientation), national origin, age, disability, genetic information, military or veteran status or any other characteristic protected by law.

About Sinclair:
Sinclair, Inc. (Nasdaq: SBGI) is a diversified media company and a leading provider of local news and sports. The Company owns, operates and/or provides services to 177 television stations in 79 markets affiliated with all major broadcast networks; owns Tennis Channel, the premium destination for tennis enthusiasts; and multicast networks CHARGE, Comet, ROAR and The Nest. Sinclair’s AMP Media produces a growing portfolio of digital content and original podcasts. Additional information about Sinclair can be found at www.sbgi.net.

About the Team:
The life-blood of our organization is our people. We have a compelling story, a goal-oriented culture, and we take really good care of people. How good? Here is a glimpse: great benefits, open-door policy, upward mobility and a strong desire to see you succeed. Ready to be part of a winning team? Let’s talk.

Please note that this position is not eligible for visa sponsorship, including employer sponsorship for an H-1B visa, OPT-STEM employment, etc.

Sinclair Broadcast Group

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