Job Description

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.

The Candidate We Are Looking For

This role requires drive, analytical rigor, and disciplined investment judgment:

• Persistent and accountable. You pursue the facts, resolve critical questions, and move workstreams forward without sacrificing judgment or process discipline.

• Conviction grounded in evidence. You advocate clearly for opportunities supported by the analysis, challenge your own assumptions, and change your view when the facts no longer support the thesis.

• A strong investment track record. You can explain your attributed role across transactions, including the original thesis, key decisions, outcomes, and lessons from investments that did not perform as expected.

• Expert financial modeling. You build and own LBO, operating, valuation, and downside models that are accurate, transparent, and designed to allow the Investment Committee to stress key assumptions.

• Rapid industry learning. You can quickly develop a credible understanding of industry structure, unit economics, competitive dynamics, and the key participants without relying solely on third-party reports.

• Driven by investment judgment. You are energized by evaluating opportunities, developing conviction through evidence, and maintaining the discipline to walk away when valuation, structure, or downside protection is inadequate.

• Relationship-oriented and direct. You build trust with founders, bankers, lenders, management teams, advisors, and colleagues while communicating candidly and maintaining intellectual honesty.

• Strong market relationships. You bring established relationships with bankers, advisors, lenders, and executives and can expand Sinclair's market coverage as the firm evaluates new industries and opportunities.

Key Responsibilities

Sourcing and Evaluation

• 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.

Transaction Execution

• 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.

Portfolio Oversight

• 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.

Team and Firm Development

• 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.

Qualifications

• 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; M.B.A. preferred but not required.

Compensation and Benefits

The base salary range for this position is $200,000 to $270,000, based on experience, plus eligibility for a discretionary performance-based annual bonus and long-term incentives. Final compensation for this
role will be determined by various factors such as a candidate’s relevant work experience, skills, certifications, and geographic location. 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.