Director, Corporate Finance, Finance & Banking

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

Start Date: Immediate

Division: Investment Banking

Post Oak Group is seeking an experienced investment banking and fundraising professional to serve as Director – Pitch Coaching & Fundraising Strategy. This is a senior, client-facing role focused on helping founders, CEOs, and management teams improve how they present their companies to investors and position their fundraising opportunities.

The ideal candidate has 5+ years of experience across investment banking, venture capital, private equity, transaction advisory, corporate finance, startup fundraising, investor relations, or a closely related field, with significant experience preparing executives for investor presentations and capital-raising conversations.

The Director will lead pitch coaching sessions, fundraising strategy meetings, and management preparation calls. The role is highly focused on improving the quality, clarity, credibility, and effectiveness of investor presentations.

This person should be able to quickly assess a company’s investment story, identify weaknesses in the pitch, anticipate investor objections, and coach management teams on how to communicate their business model, financial performance, growth opportunity, competitive positioning, valuation, and capital needs more effectively.

The Director will also help clients refine their fundraising strategy, including investor targeting, positioning, transaction timing, messaging, and meeting preparation.

This role requires strong executive presence, commercial judgment, and the ability to provide direct, constructive feedback to founders and senior executives. The successful candidate must be comfortable challenging management teams when their messaging, assumptions, presentation style, or fundraising strategy requires improvement.

This is not a junior execution role. The Director will be expected to independently lead senior-level advisory and coaching sessions while working closely with Post Oak Group’s deal teams.

• Lead pitch coaching sessions with founders, CEOs, and senior management teams.
• Prepare clients for investor meetings, management presentations, diligence calls, and follow-up discussions.
• Evaluate pitch decks and management presentations from an institutional investor perspective.
• Identify weaknesses in messaging, presentation structure, investment thesis, financial narrative, valuation expectations, and overall positioning.
• Coach executives on how to communicate their business model, market opportunity, competitive advantage, growth strategy, financial performance, and use of proceeds.
• Help management teams anticipate and respond effectively to difficult investor questions and objections.
• Advise clients on fundraising strategy, investor positioning, transaction timing, and investor targeting.
• Provide direct and constructive feedback on executive communication, presentation style, clarity, credibility, and delivery.
• Help clients strengthen their overall investment narrative and ensure consistency across pitch decks, financial models, CIMs, teasers, and investor discussions.
• Review financial forecasts, KPIs, valuation assumptions, transaction structures, and other supporting materials relevant to the pitch.
• Work closely with internal deal teams to understand each transaction and align pitch strategy with the broader fundraising process.
• Conduct role-play sessions and simulated investor meetings to prepare clients for live investor interactions.
• Identify common investor concerns and help management teams develop clear, credible responses.
• Manage multiple client engagements and coaching sessions simultaneously across different industries and business models.
• Maintain high standards…