Vice President – Startup Fundraising Advisory

Vice President – Startup Fundraising Advisory

Location: Remote

Hours: Monday–Friday, 9:00 AM–6:00 PM U.S. Central Time

Start Date: Immediate

Division: Investment Banking

Job Description

Post Oak Group is seeking a senior investment banking and fundraising professional to serve as a Vice President – Startup Fundraising Advisory. This is a senior, client-facing role focused on advising startup founders and CEOs throughout the capital-raising process.

The ideal candidate has 7+ years of experience across investment banking, venture capital, private equity, corporate finance, transaction advisory, or startup fundraising, with direct experience advising companies on institutional capital raises, ideally from Seed through Series C.

The VP will independently lead fundraising strategy and advisory meetings, help founders strengthen their investment narrative and positioning, and provide senior-level guidance on valuation, capital structure, dilution, transaction timing, investor targeting, and fundraising strategy.

This role requires strong financial judgment and the ability to evaluate companies from an investor's perspective. The VP should be comfortable identifying weaknesses in business models, KPIs, forecasts, financial narratives, valuation expectations, and investment theses, while constructively challenging founders when changes are needed.

The position also involves preparing founders for investor meetings and diligence, reviewing financial models and transaction materials, and managing multiple startup engagements simultaneously across different industries and business models.

This is not a junior execution role. The successful candidate must demonstrate executive presence, sound judgment, and the ability to independently advise sophisticated founders, CEOs, investors, and senior executives.

Responsibilities

• Serve as a senior client-facing advisor to startup founders and CEOs throughout the fundraising process.
• Independently lead fundraising strategy, advisory, and preparation meetings.
• Advise clients on fundraising strategy, valuation, capital structure, dilution, transaction timing, and investor targeting.
• Help founders refine pitch decks, investor presentations, financial narratives, and overall fundraising positioning.
• Evaluate companies from an investor perspective and identify weaknesses in the business model, financial story, growth assumptions, KPIs, valuation, and investment thesis.
• Constructively challenge founders when expectations, positioning, valuation, or fundraising strategy require improvement.
• Prepare founders for investor meetings, including anticipated diligence questions, objections, financial discussions, and presentation coaching.
• Review financial models, forecasts, valuation analyses, cap tables, and transaction materials and provide senior-level guidance.
• Work across a high volume of startup clients simultaneously and quickly understand different industries, business models, financing needs, and transaction dynamics.
• Coordinate with internal analysts and deal teams while maintaining ownership of the senior client relationship and strategic advice.
• Communicate complex financial and transaction concepts clearly to founders, executives, and investors.
• Maintain a high standard of responsiveness, professionalism, organization, and follow-through across multiple engagements.

Requirements

• 7+ years of professional experience in investment banking, venture capital, private equity, corporate finance, transaction advisory, startup fundraising, or a closely related field.
• Direct experience advising startups on capital raises, ideally from Seed through Series C.
• Strong understanding of the venture capital fundraising process, institutional investor expectations, and transaction execution.
• Demonstrated experience personally leading founder, CEO, investor, board, transaction, or capital-raising meetings.
• Strong executive presence and the ability to communicate confidently with sophisticated founders, CEOs, investors, and senior executives.
• Exceptional spoken and written English, with the ability to communicate naturally and persuasively with U.S.-based clients.
• Strong financial analysis, forecasting, valuation, and financial modeling skills.
• Advanced Microsoft Excel skills.
• Strong understanding of valuation methodologies, capital structures, cap tables, dilution, and transaction economics.
• Ability to review and provide senior-level guidance on financial models, forecasts, pitch decks, investor materials, and transaction documents.
• Strong analytical judgment and the ability to evaluate investment opportunities from an institutional investor perspective.
• Highly organized and capable of managing multiple clients, meetings, deliverables, and deadlines simultaneously.
• Strong attention to detail and consistent follow-through.
• Comfortable working independently and taking ownership of client relationships in a fast-paced, remote environment.
• Experience working with internal analysts and deal teams while maintaining responsibility for strategic client advice.
• Experience at an investment bank, VC/PE fund, Big Four transaction advisory practice, startup advisory firm, or venture-backed company strongly preferred.
• Must be available to work Monday through Friday from 9:00 AM–6:00 PM U.S. Central Time.
• Must be available to start immediately.

Why The Post Oak Group

The Post Oak Group delivers institutional-quality investment banking advisory with boutique-level service and direct senior involvement. We advise companies and business owners on complex financial transactions.