Managing Director

Remote — United States & Canada

Estimated annual earnings: US$450,000–$500,000+

Independent, success-fee-based opportunity

Windsor Drake is an independent investment bank advising founder-led companies on sell-side M&A transactions.

We are selectively adding M&A professionals to our North American advisory platform.

Completed Deal Experience Is the Primary Qualification

The single most important qualification for this role is meaningful involvement in completed M&A transactions.

We are open to candidates from investment banking, business brokerage, corporate development, private equity, accounting, law and independent advisory backgrounds. Sector pedigree and former-firm brand matter less than demonstrated transaction experience.

Applicants should provide a list of representative completed transactions or tombstones showing:

• Client or company
• Buyer or counterparty
• Transaction type
• Approximate transaction value, where public
• Closing year
• Your exact role and responsibilities
• A public announcement or other verification, where available

We are particularly interested in understanding what you personally did on each transaction—not simply which deal team you were associated with.

The Opportunity

Senior Advisors and Managing Directors will:

• Lead or co-lead sell-side M&A engagements from mandate through closing
• Work directly with founders and business owners
• Advise on valuation, positioning, buyer strategy and transaction structure
• Participate in selected new-business pitches
• Oversee buyer engagement, IOIs, LOIs, diligence and negotiations
• Work with Windsor Drake’s research, buyer-coverage and execution infrastructure
• Contribute their previous transaction experience to new client engagements
• Originate engagements where appropriate, although an existing book of business is not required

What Windsor Drake Provides

• Access to firm-originated founder and owner opportunities
• Dedicated buyer research and outbound infrastructure
• Analyst support for buyer mapping, market research and process execution
• Institutional-quality transaction positioning and materials
• Technology-sector research and market intelligence
• Meaningful participation in transaction economics
• A focused platform without the bureaucracy of a larger investment bank

Candidate Profile

The strongest candidates will have:

• Direct involvement in multiple completed M&A transactions
• The ability to explain their precise role on each transaction
• Experience advising or working with privately held businesses
• Working knowledge of valuation, buyer strategy, LOIs, diligence and closing
• The credibility and judgment to advise founders through consequential decisions
• The ability to take ownership of an engagement
• No employer restriction or conflict preventing outside advisory work

Experience in fintech, payments, software, cybersecurity, healthcare, business services, industrials or other lower-middle-market sectors is welcome. We care more about completed transactions and personal contribution than a particular sector or former employer.

Former Managing Directors, Directors, Vice Presidents, Associates, business brokers, corporate-development executives and experienced independent advisors are encouraged to apply.

Compensation

This is a fully performance-based independent contractor opportunity with no base salary or guaranteed compensation.

• Up to 25% of collected success fees on firm-originated mandates led through closing
• Up to 40% of collected success fees on advisor-originated mandates led through closing
• Additional participation for qualified introductions and specialist involvement

An active professional closing one to three transactions annually could earn approximately US$150,000–$500,000+, depending on transaction size, responsibilities and fees collected. Actual compensation is entirely dependent on completed transactions; no minimum earnings are guaranteed.

How to Apply

Please submit:

1. Your résumé or LinkedIn profile
2. A list of your completed M&A transactions or representative tombstones
3. Your exact role on each transaction
4. Public transaction announcements or verification where available
5. A short note describing the type of transactions you are best equipped to lead

Applications without transaction details may not be considered.

• All discussions will be handled confidentially. Appointments are subject to transaction verification, references, conflicts review and applicable regulatory requirements.