Account Executive

3 weeks ago

montréal, Canada Optionality Full time

I’m Simon Leroux, the founder of Optionality.AI. I’ve built and sold companies before, and I know that the best companies are built by the best people. That’s why I’m personally hiring for this role.


We are changing the way M&A and financing professionals work by building the first true AI co-pilot for dealmaking—and we’re already proving it in the market. If you’re a top performer in B2B SaaS sales, passionate about M&A, AI, and fast-moving startups, and want to be part of something truly game-changing, let’s talk.


About Optionality.AI

I founded Optionality.AI because I’ve seen firsthand how inefficient and fragmented the M&A and financing advisory industry is. We are building a Generative AI co-pilot that gives advisors an unfair advantage by making deal execution faster, smarter, and more efficient.


Our platform does what no other tool can:

  • Instantly generate business assessments and valuations
  • Create client pitchbooks and deal documents in one click
  • Build exit and value creation roadmaps
  • Map the market and generate lists of acquirers and targets
  • Streamline strategic deal documentation like teasers, CIMs, and IC memos


We launched our MVP in October and already have paying clients in the lower mid-market M&A space ($15K-$50K ACVs). We’re closing six-figure deals with private equity firms, Big 4 accounting firms, and banks. Backed by Inovia Capital, part of Google and Cohere’s AI startup programs, we are moving fast and changing the way deals get done.


Now, I’m looking for the right person to join me in taking Optionality to market. This is a rare opportunity to build something big at the intersection of AI, fintech, and M&A.


The Role

This is not a typical sales job. I need someone who can own the entire sales cycle, refine our go-to-market playbook, and help build the foundation of our sales team.


Your job is to get Optionality in front of the right people—M&A advisors, private equity professionals, and commercial bankers—and show them how AI can transform their deal pipeline and execution.


You’ll be:

  • Running a full-cycle sales process: inbound and outbound prospecting, qualifying leads, demoing, and closing deals
  • Mastering and delivering high-impact demos that make prospects realize they can’t afford to keep doing things the old way
  • Managing a strong pipeline of opportunities, from quick wins in the lower mid-market to complex enterprise deals with PE firms and banks
  • Representing Optionality at key industry events like ACG DealMax and M&A conferences
  • Building a repeatable, scalable sales process—once we have product-market fit locked in, we’ll expand the team around you


This is an opportunity to work directly with me, and our awesome team, and play a defining role in shaping how AI is applied to the M&A industry.


Who You Are

I want to work with someone who is as obsessed with M&A, AI, and data as I am. Someone who gets excited about building from the ground up, thrives in fast-moving startups, and is ready to prove they are in the top 10% of sales professionals.


You should have:

  • 3-5 years of experience in B2B SaaS sales, ideally in fintech, AI, or another high-ticket, complex sales environment
  • A track record of closing deals and consistently hitting or exceeding quota
  • A deep interest in M&A, private equity, and investment banking—you understand how these professionals think and what drives them
  • A strong ability to run an efficient sales process—you know how to qualify prospects, move deals forward, and close with urgency
  • Exceptional demo skills—you can sell a vision and make people excited about adopting new technology
  • A bias for action—you don’t wait for perfect conditions, you make things happen
  • Experience with sales tools like Hubspot, Dripify, or LinkedIn Sales Navigator


This role is not for someone who needs a lot of hand-holding. You’ll be given the freedom and support to figure out what works, and when we get traction, you’ll help build out the team.


Why Optionality.AI?
  • You’ll be the first sales hire—a foundational role in a company that’s poised for breakout growth
  • You’ll work directly with me, the founder—I’ve built and exited companies before, and I invest in top talent
  • You’ll sell a product that’s actually changing the industry—we’re not just another SaaS tool; we’re redefining how deals are done
  • You’ll have a clear path to leadership—once we dial in the sales motion, we’ll scale the team, and you’ll be at the center of it
  • You’ll be rewarded like a top performer—competitive base, best-in-class uncapped commissions, and the potential for equity


If This Sounds Like You, Let’s Talk

I’ll be personally involved in hiring for this role because I want to work with the best. If you’re a top performer in sales, passionate about M&A and AI, and want to build something truly industry-defining, let’s have a conversation.


Apply now or reach out directly.



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