Analyst / Associate

Job Responsibility: About Sycamore Advisory Currently operating as a solo GP with a caffeine addiction. I’m building a boutique M&A advisory firm focused on middle-market transactions in North America. I’ve advised private equity firms, strategic acquirers, sponsors, founders, and family-owned businesses on both buy-side and sell-side mandates. I’m currently working towards the firm’s first closed deal, about to enter diligence. If you’re looking for an incredibly structured environment, this role isn’t for you. I’m building from the ground up and I’m geeked about putting together a fully ramped team. The Role I’m hiring two Analysts or Associates (depending on experience) to support M&A origination and execution across both buy-side and sell-side mandates. You’ll work directly me (the MD) and interact with a motley crew of investors, acquirers, and business owners. You’ll get exposure to the full deal cycle - from research, outreach, diligence, close, and closing dinners. Given my finite capacity, you won’t be an excel monkey and will play an active role on live deals. I’m looking for entrepreneurial, intellectually curious, and ambitious youths to build with. Key Responsibilities

• Conduct research on industries, companies, and potential acquirers/investors.
• Build outreach materials, teasers, CIMs, and tailored buyer/investor lists.
• Support origination efforts by identifying new opportunities, qualifying prospects, and executing personalized outreach campaigns.
• Track and manage CRM workflows across active mandates and origination pipelines.
• Participate in client and acquirer calls, take notes, and manage follow-ups.
• Assist with financial benchmarking, trading/transaction comps, and light financial modeling.
• Support data room organization, diligence tracking, and process execution.
• Draft internal memos, timelines, and deal status updates.
• Contribute to pitch decks, proposals, and thought pieces to support new client engagements.
• Nurture relationships with business owners, investors, and intermediaries.

Who I’m Looking For

• 0–3 years of experience in M&A origination, advisory, investment banking, private equity, corporate development, consulting, or B2B sales.
• Intellectually curious.
• Peerless writing and analytical skills.
• Organized and detail-oriented, perhaps to a fault.
• Problem-solving mindset.
• Proficiency in Excel and PowerPoint.
• Familiarity with financial modeling (comps, DCF, precedents).
• CRM experience (HubSpot, Salesforce, etc.) is an asset.

Compensation

• Base Salary: $80,000 CAD - $100,000 CAD (commensurate with experience).
• Performance Bonus
• Deal-based Commission (10% of net success fees on deals originated).
• End-of-Year Performance-based bonus.
• 4 weeks vacation plus Sycamore will be closed for the winter break from mid-December to early January.
• Health & dental benefits.
• Education stipend.
• $50/month cell phone reimbursement.
• Toronto-based hybrid work environment (2–3 days in-office/week).

How to Apply Email your resume and a cover letter to: View email address on ca.edajobs.com. Extra points for witty and/or ironic subject lines. Puns and wordplay are encouraged. Disclaimer: Sycamore Advisory welcomes applications from qualified candidates. Please note that all applications must be candidate-initiated. We do not actively solicit or approach employees of other firms. If you are currently employed elsewhere and wish to apply, you must do so voluntarily and through this posting.