Director of People Operations
Dealmaker
| Company | Dealmaker |
| Category | Operations & Admin |
| Location | Toronto |
| Remote | Hybrid |
| Employment | Not stated |
| Level | Director |
| Salary | USD 165k |
| Posted | 31 Jul 2026 |
| Last verified | 9 Aug 2026 |
| Source | Employer ATS (ashby) |
Description
DealMaker is a fast-growing fintech company revolutionizing the capital markets ecosystem with a mission to make online capital raising mainstream. We empower founders, CEOs, and operators to raise capital digitally, both from their own communities and through strategically marketed campaigns. No other platform provides an end-to-end solution like ours—and our track record speaks for itself, with over $2B raised across 1,000+ campaigns. We power the largest online capital raises for customers like EnergyX ($88M), Green Bay Packers ($65M), Miso Robotics ($72M+), Monogram Orthopaedics (Nasdaq:MGRM) and many others, with 3 IPOs in the past year alone. We are quickly expanding our horizons and are seeking talented team members to join us on our journey to transform the global capital market.
ABOUT DEALMAKER, FROM THE PEOPLE PERSPECTIVE
We are approximately 200 people across Toronto, Los Angeles, New York, and Medellín, operating at the intersection of technology, performance marketing, capital markets, and customer experience.
Our co-founders built their careers as capital markets lawyers, and that discipline still shapes how we operate. We encourage decisions to have a clear reason behind them, leaders to know their business, and people to take real ownership of outcomes.
We move quickly, speak directly, and care more about solving the problem than protecting the process. We are building a lean, AI-enabled company where strong people are trusted with meaningful responsibility and expected to use judgment.
The People team plays an important role in making that possible. Our job is not to add layers or slow the company down. It is to build the systems, leadership capability, and operating clarity that help great people do their best work.
ABOUT THE ROLE
This is a senior, hands-on leadership role for someone who wants to build the operating backbone of a modern People function.
You will lead the systems and practices that allow DealMaker to scale responsibly across Canada, the United States, and Colombia. That includes employment compliance, employee relations, compensation, performance programs, People data, and the day-to-day operating standards of the team.
You will also be a trusted advisor to our executives and leaders. You will be expected to bring judgment, challenge unclear thinking, and help leaders make sound decisions before issues become problems.
This is not a role for someone who wants to operate only at the strategy level. You will set direction, build the system, and stay close enough to the work to know whether it is actually working.
THE OPPORTUNITY
DealMaker has already built many of the foundations of a strong People function. The opportunity now is to make those foundations more consistent, scalable, and connected to how the business operates.
You will have the mandate to improve core People systems, raise the quality of leadership decisions, and build a function that is trusted because it is practical, responsive, and commercially grounded.
You will work closely with the VP, People and executive team, lead a capable operating team, and have meaningful influence over how DealMaker grows.
WHAT YOU’LL OWN
- Build and lead DealMaker’s People Operations model across Canada, the United States, and Colombia, creating clear standards without unnecessary bureaucracy
- Use AI thoughtfully to evolve People programs, workflows, and practices across the team, improving speed, quality, and employee experience without automating away sound judgment.
- Own DealMaker’s employment compliance operating system, partnering with legal counsel, local experts, payroll providers, and EOR partners where needed
- Lead complex and legal-adjacent employee relations matters, balancing sound business judgment, employee care, consistency, and risk
- Own the company’s compensation philosophy and operating practices so pay decisions are consistent, competitive, and supported by clear reasoning
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