We are expanding.
Diamond Willow Advisory is not your typical financial services firm. We help ambitious, mid-market businesses access the capital they need to grow, transform, or survive. Our specialty is complex corporate debt transactions, and we bring clarity, urgency, and execution horsepower to situations where others fall short.
We are hiring senior business originators in Vancouver, Calgary, Edmonton, and Toronto who can do more than just win deals, you’ll also cultivate and lead a community of trusted, like-minded professionals committed to helping mid market businesses succeed. This is a senior, high-intensity origination role for someone who doesn’t need handholding, takes pride in their work ethic, and wants ownership of a region they will be known for building and expanding.
The Role
You will be the face of Diamond Willow in your market, working directly with mid-sized business owners to seasoned management teams, lenders, accountants, lawyers, and other trusted advisors. You’ll originate deals, present to groups, screen opportunities, and structure financing solutions.
Beyond origination, you’ll build a professional ecosystem, hosting conversations, forging alliances, and bringing together people who share our vision of empowering ambitious business leaders. Your influence will extend beyond individual transactions to shaping a network that drives opportunity for years to come. Execution support comes from our team in Calgary, so you can focus on what matters most: building trust, finding opportunities, nurturing community, and delivering value. We value entrepreneurial drive, and for the right person, this role is a steppingstone to partnership.
This role is for someone who is:
• Relentlessly ambitious and ready to test their entrepreneurial spirit
• Confident, not arrogant
• Financially fluent and strategically minded
• Uncompromising in ethics with a client-centric mindset
Must-Haves
• A track record of grinding through complex situations and coming out ahead
• Experience in finance, lending, accounting, family office, sales, restructuring, or insolvency
• Immune to rejection and too stubborn to quit
• Proven sales instinct with a drive to originate new business
• Strong presentation and relationship-building skills
• The desire to build a long-lasting community of high functioning professionals
Nice-to-Haves
• Background in private equity/private credit, capital markets, corporate finance, family office
management, mergers and acquisitions, special situations, or restructuring
• Designation such as CFA, CPA, CIRP, LIT, or CBV
• A well established local network
What We Offer
• The kind of opportunity that turns careers into legacies – but only for those who can match our pace,
intensity, and client-first obsession
• Competitive base salary with uncapped commission upside
• A lead role in launching and owning a key market
• Full support from a seasoned deal execution team in Calgary
• The chance to create a lasting professional community that advances mid-market business growth
• A high-integrity firm that puts long-term reputation above short-term fees
Who we are.
Our Purpose
We exist to enable the ambitions of those who have chosen to be more and serve as a rallying point for a community of like-minded professionals who support them.
Our Mission
To help ambitious business leaders meet their potential by enabling access to the capital and expertise they need to achieve their goals.
Our Vision
To establish a standard of execution by which others in our industry will be measured.
Our Values
• Ambition – Because without it, we simply don’t exist
• Empathy – Because our work has a significant impact on people’s lives
• Creativity – Because it’s what sets up apart and deepens our moat
• Effort – Because we choose not to rely on intelligence alone
• Steadfastness – Because the shortcuts are easy but that’s not where we’re going
Our Promise
We will never sacrifice an ounce of reputation no matter how tempting the prize.
Our People
We are a small team with backgrounds in investment banking, equity research, private equity, and accounting. What unites us is our intensity, loyalty, long-term thinking, and relentless focus on building community and serving clients. We put the brand and our reputation ahead of personal gain, every time. If you’re looking for comfort, this isn’t it. But if you want to build something lasting – let’s talk.
We believe the best teams are built on diverse experiences and perspectives. If you're aligned with our values and mission, we want to hear from you – even if your background doesn’t match every line of this posting.
