Investment Banking Assistant (Remote)

Windsor Drake is a boutique investment bank focused on sell-side M&A for founder-led businesses, primarily in software, fintech, payments, and tech-enabled services. We run lean, move fast, and operate at a high professional standard.

We are hiring an Investment Banking Assistant to support live deal execution and outbound buyer outreach. This is not a generic VA role. This is an analyst-style position for someone with a real finance background who understands how M&A processes actually work.

Core Responsibilities

Buyer Research & Mapping

Research and identify strategic and financial buyers for active sell-side mandates

Build clean, well-reasoned buyer lists based on industry fit, size, geography, and acquisition history

Use LinkedIn, company websites, press releases, and deal databases to validate relevance

Think critically about why a buyer makes sense, not just whether they exist

Cold Email Outreach (Buy-Side)

Send outbound emails to potential buyers on behalf of Windsor Drake

Personalize outreach based on buyer profile and transaction rationale

Manage follow-ups and keep outreach organized and systematic

Track responses and engagement levels

Inbound Management & Qualification

Monitor inbound interest from buyers

Qualify buyers based on seriousness, mandate fit, and decision-maker level

Organize buyer responses and escalate high-quality interest to the Managing Director

Keep the process clean, professional, and responsive

Deal Support

Assist with managing the buyer funnel throughout the process

Track outreach status, responses, and next steps

Support NDA tracking, follow-ups, and basic process logistics

Maintain internal deal trackers and notes

Requirements (Non-Negotiable)

Finance, accounting, economics, or business background

Strong understanding of M&A, private equity, or corporate finance fundamentals

Excellent written English, professional and concise

Comfortable with cold outbound email and follow-up

Highly organized and detail-oriented

Able to work independently with clear instructions and high expectations

Preferred Experience

Prior experience in investment banking, private equity, corporate development, or transaction advisory

Experience building buyer lists or doing deal research

Familiarity with CRM tools, spreadsheets, and basic deal tracking

Comfortable communicating with senior executives at acquiring companies

What This Role Is Not

Not a data-entry role

Not a generic VA position

Not social media, marketing, or customer support

Not a training-from-zero role

You are expected to already understand the basics of how deals work and how buyers think.

Compensation & Growth

Competitive pay for a finance-skilled role

Long-term opportunity for strong performers

Direct exposure to live M&A transactions

Clear path to increased responsibility over time

How to Apply

Please include:

A brief summary of your finance and deal-related experience

Examples of buyer research or outbound work you’ve done (if applicable)

Your availability and time zone

We are looking for someone sharp, reliable, and commercially minded. Precision and judgment matter. Execution matters more.