Director

Location: Remote

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 robust 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.

Responsibilities

- 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 of professionalism, responsiveness, preparation, and follow-through.

Requirements

- 5+ years of professional experience in investment banking, venture capital, private equity, transaction advisory, corporate finance, startup fundraising, investor relations,



or a closely related field.
- Significant experience working directly with founders, CEOs, management teams, investors, or senior executives.
- Demonstrated experience leading investor presentations, pitch preparation, fundraising strategy meetings, or executive coaching sessions.
- Strong understanding of institutional investor expectations and how investors evaluate companies and transactions.
- Ability to quickly identify weaknesses in investment narratives, business models, financial assumptions, positioning, and presentation materials.
- Strong executive presence and the ability to provide candid, constructive feedback to senior executives.
- Exceptional spoken and written English, with the ability to communicate naturally and persuasively with U.S.-based clients.
- Strong understanding of fundraising strategy, valuation, capital structure, dilution, investor targeting, and transaction dynamics.
- Ability to review pitch decks, financial models, forecasts, CIMs, teasers, and investor materials from a strategic perspective.
- Solid analytical and commercial judgment.
- Excellent presentation, communication, and coaching skills.
- Ability to manage multiple clients, meetings, and deadlines simultaneously.
- Highly organized with strong attention to detail and consistent follow-through.
- Comfortable working independently and taking ownership of senior-level client interactions in a fast-paced remote environment.
- Experience at an investment bank, VC/PE fund, Big Four transaction advisory practice, startup advisory firm, or venture-backed company strongly preferred.
- Experience coaching executives or preparing management teams for investor presentations 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 and help management teams communicate their opportunities effectively to sophisticated investors.

📌 Director (Canada)
🏢 Post Oak Group
📍 Canada