Careers

Everything follows from who we hire.

Windsor Drake is a small, senior-weighted firm. The quality of the team determines the quality of the process, and the process determines the client’s outcome. So we hire rarely, hold an exacting standard, and hand the people we choose real responsibility from the first week.

Toronto · New York · Senior-led · No layers
The Standard

We hire on how you work, not your pedigree.

A boutique does not have the structure to absorb passengers. Everyone carries real responsibility from the start — and the people who do their best work here prefer it that way. We look for five things.

01
Analytical discipline
Financial modeling, comparable analysis, and document preparation demand consistent accuracy. There is no review committee to catch errors. You own the output.
02
Written communication
Transaction materials, buyer correspondence, and research must be clear, precise, and free of filler. Writing is a core competency here, not a secondary skill.
03
Self-direction
You will run multiple workstreams across concurrent engagements. The expectation is that you identify what needs doing, prioritize, and execute without waiting to be told.
04
Discretion
Every engagement involves confidential information about private companies and their owners. Judgment about what to share, when, and with whom is non-negotiable.
05
Intellectual curiosity
Our sectors move quickly. Staying current on market dynamics, buyer behavior, and valuation is part of the work, not optional enrichment.
The Work
No layers 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. There is no middle management between you and the mandate.

The learning curve is steep by design. The experience you gain in the first year is comparable to what many large-firm analysts see over two or three, because the scope of what you touch is broad and the distance between your work and the outcome is short.

Team members also contribute to the firm’s quarterly research program: public-company benchmarking, comparable transactions, and market intelligence that informs how every engagement is positioned.

The quality of the team is the firm.
The quality of the team determines the quality of the process. The process determines the outcome for the client. Everything follows from who we hire.
Operating Standards

The standard does not move.

Precision over volume
We take a limited number of engagements and execute each at a high standard. The same applies to internal work: models, materials, and communications are accurate, clear, and complete before they leave your desk.
Direct responsibility
No separate team for research, outreach, or review. You are the deal team. The scope is broad and the feedback loop between your work and the outcome is short.
Confidentiality as a baseline
Every engagement involves sensitive information about private companies and their owners. The standard for handling it is absolute — internally and externally, in every document you produce.
Merit-driven advancement
Advancement follows 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.
Open Positions

Where we are hiring.

Positions are listed when available. Every application is read by a senior professional. If nothing fits today, strong credentials are kept on file for future consideration.

Toronto / New York
Investment Banking Analyst
Support live sell-side M&A engagements through financial analysis, transaction document preparation, buyer research, and process coordination.
Strong financial modeling, excellent written communication, and comfort across multiple concurrent mandates. Prior experience in investment banking, private equity, corporate finance, or management consulting is preferred.
Apply
Toronto / New York
Associate / Vice President, Deal Execution
Lead day-to-day execution on sell-side mandates: buyer outreach, competitive process management, negotiation support, and due diligence coordination.
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.
Apply

No opening that matches your background? Submit your credentials anyway. The firm keeps strong candidates on file, and every submission is reviewed by a senior professional.

The Process

How we hire.

01
Screen
An initial review of your background and a short conversation about your interest in sell-side M&A and the firm.
02
Technical & case
A technical and case-based interview that tests financial and analytical competence and the clarity of your thinking under time pressure.
03
Final
A conversation with senior leadership on judgment, communication, and fit. We move efficiently and give clear, timely decisions.
Common Questions

Careers FAQ

What experience do you look for in analysts?
We prefer prior experience in investment banking, private equity, corporate finance, or management consulting, with strong financial modeling, Excel proficiency, and demonstrated writing ability. Candidates with relevant internships or strong academic credentials in finance, economics, or a quantitative discipline are also considered.
Does Windsor Drake hire interns?
On a selective basis. Interns are assigned to live engagements and work alongside the deal team on transaction materials, buyer research, and financial analysis.
Are roles in-office or remote?
Windsor Drake works from offices in Toronto and New York. Live transaction execution with direct client contact requires regular in-office presence; some roles offer hybrid flexibility depending on seniority.
What sectors will I work in?
The firm's coverage verticals are fintech, cybersecurity, B2B SaaS, and AI software. Team members build sector depth through direct transaction experience and the firm's quarterly research program.
How does compensation work?
A base salary plus performance-based incentives tied to individual contribution and firm outcomes. The firm's fee structure is success-weighted, so strong performance directly influences team economics. Specifics are discussed during the process.
What does the interview process involve?
An initial screen, a technical and case-based interview, and a final conversation with senior leadership. We assess analytical competence, communication quality, and fit, and give clear, timely decisions.
Apply

If you hold yourself to this standard, we should talk.

Send your resume and a brief note on your interest in sell-side M&A at Windsor Drake. Every application is read by a senior professional, and strong credentials are kept on file even when no role is open.

Submit Your Credentials

Windsor Drake is an equal-opportunity employer. Selection is made on merit — the quality of your work and judgment — without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.