M&A Advisor

Succession AI; Toronto; On-site; CAD 80,000 - 120,000; Full time

Benefits offered by this job

Equity

Job summary

Succession AI, based in Toronto, is seeking an M&A Advisor to lead deals end-to-end, leveraging AI to accelerate value in North American SMB transactions. You will own origination, diligence, negotiations, and close from Day 1 in a fast-growing, founder-led environment.

You bring 3–7 years of M&A experience (Big 4 or mid-market), a CPA is a strong asset, and you will train AI tools, shape processes, and manage buyer relationships with autonomy amid a lean team.

Qualifications

• 3–7 years of M&A experience at a Big 4 deal advisory practice, mid-market or boutique M&A firm, or in an equivalent sell-side or corporate development role on small and mid-market transactions.
• A CPA designation is a strong asset.
• You've done the reps (CIMs, models, LOIs), so you're ready to work in ways that didn't exist five years ago, with AI handling the busywork while you focus on what moves the deal.
• You’ll own the full lifecycle: origination, diligence, negotiation, and close.

Responsibilities

• Own the Full Deal Cycle: Drive transactions from engagement to close.
• Convert Warm Leads into Engagements: Build trust fast and convert conversations into signed sell-side mandates.
• Leverage AI as Your Force Multiplier: Use AI for valuations, CIM creation, buyer sourcing, deal analytics, and diligence prep.
• Shape the Product and Train the AI: Help design processes and train internal AI products with your deal expertise.
• Manage Buyer Relationships: Build and maintain a network of buyers across North America.

Skills

M&A experience

Deal origination

Negotiation

Relationship-building

Leadership

AI affinity

Education

CPA designation

Tools

Financial modeling tools

Job description

Every year, hundreds of thousands of small business owners in North America decide it's time to sell. And most of them will fail to sell it.

M&A has not fundamentally changed in decades. Traditional investment banks are built for bigger deals and oversized teams. Business brokers will take the call, but most don't have the horsepower to run a process that maximizes value. The result: business owners underserved at the biggest financial moment of their lives.

About Succession AI

Succession AI is the AI-native M&A advisory firm built for small and medium-sized businesses with $1M-$30M in revenue. We're not selling software; we're building what a modern investment bank looks like when it's designed from the ground up around AI and the needs of business owners. Our AI automates the mechanical work that used to eat 70% of an advisor's week, enabling our advisors close deals 3x faster than the industry norm.

Why Join Us

• Rapid Momentum. Join one of Canada’s fastest-growing AI-native M&A advisory firms, with institutional partnerships, proprietary valuation tools, and an expanding buyer network that creates opportunities from Day One.
• Untapped career growth potential. Help define what modern M&A looks like by combining world-class advisory with AI. Gain responsibility, autonomy, and leadership opportunities that would take years to earn at a traditional M&A firm.
• In-person culture. Based in Toronto, you will work in-person with our founding team from Day 1.
• World-class Investors & Impact. Backed by over $1M from top venture investors across the U.S. and Canada, including Comma Capital, Hustle Fund, and StandUp Ventures.
• Founding Ownership. As a small, lean team, every hire carries outsized impact. You’ll own transactions end-to-end while helping build the advisory function, playbook, and team from the ground up.

About The Role

You'll be Succession AI's key M&A Advisor hire, reporting directly to the CEO and working shoulder-to-shoulder with the founding team. At a traditional bank, you might wait a decade to own a sector or make a name for yourself. Here, that clock starts on day one: you'll run deals end-to-end, refine your M&A playbook with our AI agents, and grow into a leadership role as the team scales.

Who You Are

• Battle-Tested, Excited About AI. 3-7 years of M&A experience at a Big 4 deal advisory practice, mid-market or boutique M&A firm, or in an equivalent sell-side or corporate development role on small and mid-market transactions. A CPA designation is a strong asset. You've done the reps (CIMs, models, LOIs, closings), so you're ready to work in ways that didn't exist five years ago, with AI handling the busywork while you focus on what moves the deal.
• Closer, Not Coordinator. You didn’t get into M&A to live inside a spreadsheet. You’ve run live deals and are ready to own the full lifecycle: origination, diligence, negotiation, and close. You’re fluent in the financial fundamentals, and your edge is getting deals over the line.
• Relationship-Builder, Results-Driven. For most owners, selling a business is the single biggest, most emotional financial decision they will ever make. You can sit with that. You can hold a hard conversation about valuation or timing without flinching, and read a room well enough to know when to push and when to just listen.
• Hands-On, Hungry to Build. We're small and we move fast. When something’s messy, you organize it and push it to resolution without waiting for backup.

What You'll Do

• Own the Full Deal Cycle. Drive transactions from engagement to close. You'll manage timelines, anticipate bottlenecks, and guide founders through the emotional weight of selling their life's work, with real autonomy to run and close deals from the start.
• Convert Warm Leads into Engagements. Our owner-facing product and partnership network generate a steady stream of business owners exploring their options. You'll engage these leads, build trust fast, and convert conversations into signed sell-side mandates.
• Leverage AI as Your Force Multiplier. The platform hands you a running start on valuations, CIM creation, buyer sourcing, deal analytics, and diligence prep for every deal you lead. You bring the judgment, empathy, and negotiation instincts that win deals.
• Shape the Product and Train the AI. You're not just a user of our tools; you're helping build them. When a process doesn't exist yet, you’ll design it firsthand, and then work with engineering to automate it. Your deal expertise directly trains our internal AI products. Every deal you run makes the platform sharper and smarter for the next one.
• Manage Buyer Relationships. Build and maintain a network of qualified buyers: private equity firms, search funds, strategic acquirers, and individual buyers across North America. Run competitive sale processes that get sellers the best outcome.

Compensation

• Base Compensation CA$80K – $120K
• Offers Equity
• Uncapped commission
• Top performers earn $400K-$600K+ total comp