Senior IT Support Engineer
DealMaker
IT, Customer Service
Toronto, ON, Canada
Posted on Aug 12, 2025
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.
Who you are
We are looking for an experienced and highly skilled Senior IT Support Engineer to join our team, reporting directly to the Senior Director, Platform & Security. This position is based in our Toronto headquarters. As a key member of our IT team, you will be an individual contributor with a significant impact. We are moving past the traditional IT Services group of “fighting fires” and are always looking for ways to proactively automate and save our employees precious time. You are someone who gets excited about finding innovative solutions, simplifying complex problems, and obsessing over the internal customer experience. You have a track record of driving outcomes and aren't afraid to be bold and direct to push for a better way of doing things.
This is a 5 days/week Mon-Fri in office role in our Toronto headquarters.
What you will do
- Own and Innovate Employee Lifecycle Processes: Manage and continuously improve the onboarding and offboarding experience for team members across all our geographic regions, with a strong focus on administrative IT support. This includes provisioning and configuring hardware, coordinating the shipping and receiving of equipment, creating accounts, and ensuring all necessary tools and resources are in place for a seamless transition in and out of the company.
- Provide Timely and Empathetic Support: Deliver exceptional IT support to our team during regular business hours. You'll be expected to not just fix issues, but to document them meticulously, creating a system of procedures that helps us scale our support.
- Administer Core Business Systems: Take ownership of the administration of key company platforms including Google Workspace, Microsoft 365, MDM tools (like Kandji, JumpCloud, or Jamf), Slack, and 1Password.
- Drive Technological Evolution: Constantly evaluate new technologies and contribute to the design and improvement of our IT infrastructure. You'll be empowered to find ways to make our systems more efficient, secure, and user-friendly.
- Maintain System and Asset Integrity: Conduct regular audits of our devices and systems to ensure our IT asset and inventory databases are accurate and up-to-date. You will also own the procurement and logistics of new hardware and software.
- Automate and Simplify: Troubleshoot and enhance our automation platforms like Zapier, Jira, and Slack. You'll be a key player in finding new ways to automate workflows and simplify processes for the entire organization.
What skills you need
- Extensive IT Support Experience: 5+ years of experience in a demanding IT Support role, preferably in a fast-paced, high-growth environment.
- Deep Technical Expertise: Mastery in managing and troubleshooting both macOS and Windows operating systems.
- Expert-Level System Administration: Proven expertise in administering Google Workspace, Microsoft 365, and modern MDM Tools (Kandji, JumpCloud, Jamf) for device management, authorization, and reporting.
- Security-First Mindset: Demonstrated ability to implement and manage security best practices, including enforcing MFA, disk encryption, device compliance policies, patch enforcement, and phishing prevention training.
- Networking Proficiency: Experience with the configuration, diagnosis, and security of business network infrastructure.
- Project Leadership: Experience leading small technical projects, including defining outcomes, creating project plans, and ensuring on-time delivery.
- Automation and Scripting Skills: Proficiency in Python and Shell scripting for system automation and interconnection. Demonstrable experience using AI automation to improve workflow efficiency is a strong plus.
- A Track Record of Improvement: A history of evaluating new technologies and successfully developing and implementing IT infrastructure improvements that have a real impact.
Founded in 2018 by leading capital markets lawyers, DealMaker has blazed its own trail as the leading online capital-raising platform. As a Series 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)
-Strong autonomy with support from leadership
-Annual learning support And more!
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.