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

• 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 strong systems, automation, AI-enabled workflows, and clear service standards

• Establish operating metrics that show whether People programs are working and where intervention is needed

What Success Looks Like

Within your first year:

• DealMaker has a clear and reliable compliance operating model across all jurisdictions

• Compensation, promotion, and performance decisions are more consistent and easier for leaders to explain

• Complex employee matters are handled earlier, more confidently, and with better documentation

• 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

• Core People workflows are simpler, faster, and increasingly automated

You’ll Thrive in This Role If You Have

• 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

• A track record of personally leading complex employee matters, not only reviewing the work of others

• Experience managing compensation, promotion, and performance processes

• Experience designing or implementing compensation philosophy and pay practices

• Strong judgment and the confidence to advise senior leaders directly

• Experience building systems, processes, and controls in a growing company

• The ability to move between strategic thinking and detailed execution

• Strong written communication and documentation skills

• A practical, commercially grounded approach to People work

Extra Credit

• Experience with US employment practices

• 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

• Experience in an organization of approximately 150–500 employees

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.As a tech startup, we are well-capitalized, firmly established in our market, and ready to scale. Here’s why you should want to join us:

• Competitive compensation with the opportunity to earn equity—get into a growth company on the ground floor

• A diverse & distributed team of doers, innovators, and experts

• 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. These tools may assess job-related qualifications such as skills, experience, and work history. AI-assisted tools support our recruitment team and do not replace human judgment; all final hiring decisions are made by human reviewers.

Applicants may request information about the use of these tools or request an alternative selection process by contacting us at Talent@dealmaker.tech. For 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.

Please inform us if you require any accommodation, and we will work with you to meet your accessibility needs. For any accessibility-related assistance, requests for information in accessible alternative formats or to report any accessibility problems, please share in your application.