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. 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. 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. We encourage decisions to have a clear reason behind them, leaders to know their business, and people to take real ownership of outcomes.

We are building a lean, AI-enabled company where strong people are trusted with meaningful responsibility and expected to use judgment. It is to build the systems, leadership capability, and operating clarity that help great people do their best work. This is a senior, hands-on leadership role for someone who wants to build the operating backbone of a modern People function.

That includes employment compliance, employee relations, compensation, performance programs, People data, and the day-to-day operating standards of the team. You will be expected to bring judgment, challenge unclear thinking, and help leaders make sound decisions before issues become problems. You will set direction, build the system, and stay close enough to the work to know whether it is actually working.

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. 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 Lead performance, compensation, and promotion cycles, ensuring outcomes reflect real contribution and are applied with discipline across the organization Own the quality and integrity of People data, reporting, and decision support so leaders can act on accurate information Partner directly with members of the executive team, helping them navigate performance, leadership, team, and organizational decisions Set the operating standards for People policies and programs, translating company strategy into practical systems that managers and employees can use Shape and deliver manager and leadership development in partnership with the People Partner and VP, People Lead, coach, and develop the People Partner, Office Operations & Engagement Manager, and People Operations Manager & Payroll Improve the efficiency of the People function through solid systems, automation, AI-enabled workflows, and clear service standards Compensation, promotion, and performance decisions are more consistent and easier for leaders to explain Leaders see the People team as a practical thought partner,



not simply a policy function People data is accurate, accessible, and actively used in business decisions The People Operations team has clear ownership, strong standards, and a reputation for dependable execution 7+ years of progressive People Operations, HR, or employee relations experience, including meaningful leadership responsibility ~ Direct, hands-on experience with Canadian employment law and employee relations ~ Experience managing compensation, promotion, and performance processes ~ Strong judgment and the confidence to advise senior leaders directly ~ Experience building systems, processes, and controls in a growing company ~ Experience working with an EOR or supporting employees in Latin America Experience owning an HRIS, People analytics, or HR data infrastructure Experience supporting a founder-led or high-growth company Experience designing leadership or manager training This is a hybrid, Toronto based role (4 days in-office in Downtown Toronto).

Founded in 2018 by leading capital markets lawyers, DealMaker has blazed its own trail as the leading online capital-raising platform.Competitive compensation with the opportunity to earn equity—get into a growth company on the ground floor Shared employee benefit plan (medical, vision, & dental) We love AI and have tools to support you build innovative solutions Annual learning support And more! We use automated and artificial intelligence-based tools (“Automated Employment Decision Tools”) to assist in screening, assessing, or evaluating candidates. AI-assisted tools support our recruitment team and do not replace human judgment; Applicants may request information about the use of these tools or request an alternative selection process by contacting us at [email protected] more information about how personal information is collected and used, please see our Privacy Notice.

Equal Employment Opportunity DealMaker does not discriminate in hiring or terms and conditions of employment because of an individual’s race, ancestry, colour, place of origin, religion, gender, gender identity, national origin, citizenship, age, disability, sexual orientation, family status or marital status, or any other protected category recognized by provincial or federal laws.

📌 Head of EMEA People Operations (Toronto)
🏢 DealMaker
📍 Toronto