Home / Careers
Windsor Drake advises exceptional founders through defining transactions. Every deal is high stakes. Every mandate, high impact. Behind them is a lean team of sharp, driven professionals who operate with precision, discretion, and long-term vision. If you hold yourself to the highest standards, we want to hear from you.
Windsor Drake operates a small, senior-weighted team across offices in Toronto and New York. The firm advises on sell-side M&A transactions for companies with $1M–$10M in EBITDA across fintech, cybersecurity, B2B SaaS, and AI software.
The team is structured to give junior professionals direct exposure to live transactions from the outset. There are no layers of middle management between you and the deal. Analysts and associates work alongside the senior professionals leading each engagement—on buyer outreach, financial analysis, transaction materials, and process management.
This means the learning curve is steep. It also means the experience you gain in the first year is comparable to what many large-firm analysts encounter over two to three.
Windsor Drake is an equal opportunity employer. We value diverse perspectives and foster a merit-based, inclusive environment. All qualified candidates will be considered without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.
A boutique platform with a selective team. No layers, no bureaucracy. You work on founder-led M&A transactions from day one with direct exposure to senior dealmakers and live mandates.
Mentorship from senior dealmakers. Exposure to real transactions across the full deal lifecycle. Clear paths to advancement. We invest in your trajectory because your growth drives ours.
Modern flexibility paired with old-school values. Trust, integrity, and doing the right thing. Our clients expect excellence, and so do we. Performance is rewarded. Results are what matter.
We do not hire based on pedigree alone. What matters is how you work: the precision of your analysis, your ability to manage complexity under time pressure, and whether you hold yourself accountable to the quality of the output without being asked.
A boutique advisory firm does not have the structure to absorb passengers. Every person on the team carries real responsibility from the start. The professionals who thrive here are the ones who prefer that.
Positions are listed when available. If no openings match your background, we encourage you to submit your credentials for future consideration. All applications are reviewed by senior professionals.
TORONTO / NEW YORK
Investment Banking Analyst
Support live sell-side M&A engagements through financial analysis, transaction document preparation, buyer research, and process coordination. Candidates should have strong financial modeling skills, excellent written communication, and comfort working across multiple concurrent mandates. Prior experience in investment banking, private equity, corporate finance, or management consulting is preferred.
TORONTO / NEW YORK
Associate / Vice President, Deal Execution
Lead day-to-day execution on sell-side mandates including buyer outreach, competitive process management, negotiation support, and due diligence coordination. Requires 2–6 years of relevant transaction experience in M&A advisory, private equity, or corporate development. Sector depth in fintech, cybersecurity, or B2B SaaS is valued.
Precision over volume. We take a limited number of engagements and execute each at a high standard. The same expectation applies to internal work product. Financial models, transaction materials, and client communications are expected to be accurate, clear, and complete before they leave your desk.
Direct responsibility. There is no separate team for research, no separate team for outreach, and no separate team for document review. You are part of the deal team. The scope of what you touch is broad, and the feedback loop between your work and the transaction outcome is short.
Confidentiality as a baseline. Every engagement involves sensitive information about private companies and their owners. The standard for information handling is absolute. This applies to internal conversations, external communications, and every document you produce.
Merit-driven advancement. Advancement at Windsor Drake is based on the quality of your work and your contribution to client outcomes. The firm is small enough that strong performers are visible immediately and compensated accordingly.
The quality of the team determines the quality of the process. The quality of the process determines the outcome for the client. Everything follows from who we hire.
Windsor Drake is a sell-side M&A advisory firm focused on founder-led companies with $1M–$10M in EBITDA across fintech, cybersecurity, B2B SaaS, and AI software. The firm runs structured competitive sale processes—identifying and engaging the full universe of relevant acquirers, managing competitive tension, and executing through close.
Working in sell-side M&A advisory at the lower middle market level offers a fundamentally different experience from large-bank investment banking. Transactions are smaller but the scope of individual responsibility is larger. Analysts and associates at a boutique firm like Windsor Drake participate in every phase of a transaction: from the initial client engagement and exit readiness assessment, through CIM preparation and buyer outreach, to negotiation and close. The experience is hands-on and transaction-complete in a way that large-bank roles—where junior staff are often confined to modeling or pitch support—are not.
In addition to transaction execution, team members contribute to Windsor Drake’s quarterly sector research program, which publishes valuation and M&A reports across the firm’s coverage verticals. This research involves public company benchmarking, comparable transaction analysis, and market intelligence that directly informs how the firm positions client engagements.
For professionals interested in technology-focused M&A—particularly in fintech, cybersecurity, or B2B SaaS—the firm offers a depth of sector exposure and transaction involvement that is difficult to replicate at larger institutions.
Submit your resume and a brief note explaining your interest in sell-side M&A advisory at Windsor Drake to [email protected]. All applications are reviewed by senior professionals. If there is no current opening aligned with your background, your credentials are retained for future consideration.
We prefer candidates with prior experience in investment banking, private equity, corporate finance, or management consulting. Strong financial modeling skills, proficiency in Excel, and demonstrated written communication ability are expected. Candidates with relevant internship experience or exceptional academic credentials in finance, economics, or a quantitative discipline are also considered.
We consider internship candidates on a selective basis. Interns are assigned to live engagements and work alongside the deal team on transaction materials, buyer research, and financial analysis. Internship inquiries should be directed to [email protected].
Windsor Drake operates from offices in Toronto and New York. The nature of the work—live transaction execution with direct client interaction—requires regular in-office presence. Some roles offer flexibility for hybrid arrangements depending on the position and seniority.
The firm’s primary coverage verticals are fintech, cybersecurity, B2B SaaS, and AI software. Team members develop sector depth through direct transaction experience and contribution to the firm’s quarterly research program.
Compensation includes a base salary and performance-based incentives tied to individual contribution and firm outcomes. Specific details are discussed during the interview process. The firm’s fee structure is success-weighted, which means strong individual performance directly influences team economics.
The process typically includes an initial screen, a technical and case-based interview, and a final conversation with senior leadership. We evaluate financial and analytical competence, communication quality, and cultural fit. The process is efficient—we respect candidates’ time and aim to provide clear, timely decisions.
Windsor Drake is an equal opportunity employer. All qualified candidates are considered without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. We evaluate candidates on the quality of their work, their analytical rigor, and their commitment to the standards the firm requires.
We’re always interested in hearing from exceptional professionals. Reach out through our contact page to start the conversation.
All inquiries are strictly confidential.
Sell-side M&A advisory for founders.
©2026 Windsor Drake