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

DealMaker is the leading platform for online capital raising, powering offerings across multiple securities frameworks. Our Product Tech Support function sits at the intersection of product, engineering, and customer experience, helping issuers and investors navigate complex workflows and resolving technical issues quickly and effectively.

We’re looking for a Product Technical Support Engineer who combines strong hands-on technical skills with the ability to think beyond individual tickets and improve how support works over time. You’ll own day-to-day support operations, investigate and resolve technical issues end-to-end, and contribute to improving the processes, tooling, and standards that support the function.

This is not a ticket-queue role. You’ll be expected to understand the platform deeply, identify patterns, surface systemic issues to Product and Engineering, and help evolve how support operates, including exploring opportunities to use AI tools more effectively. As the team grows, you’ll play an important role in shaping how it scales.

What You’ll Do

Own Technical Support Operations

• Act as the primary owner of incoming support requests, ensuring timely, high-quality responses across all channels

• Triage and investigate issues using logs, error messages, APIs, and internal tools

• Resolve straightforward issues independently and escalate complex ones with clear, well-structured context

• Follow issues through to resolution, maintaining accountability for the end-to-end customer experience

• Serve as a go-to resource for more complex escalations involving platform behavior, payments, or edge cases

Debug and Problem Solve

• Analyze system behavior to identify root causes across the platform, not just surface symptoms

• Use logs, APM tools, dashboards, and basic SQL to troubleshoot issues systematically

• Build platform knowledge over time to handle increasingly complex cases with greater independence

• Document findings in ways that are reusable by the team and actionable by Engineering

Identify Patterns & Improve Processes

• Look across support tickets to identify recurring issues and systemic gaps

• Contribute to improving support workflows, escalation paths, prioritization logic, and triage processes

• Help maintain and improve documentation and knowledge bases that support both human workflows and tooling

• Suggest practical improvements that reduce support volume, improve response quality, or increase efficiency over time

Contribute to Tooling & Efficiency (Including AI)

• Identify opportunities to improve support workflows through better use of tools and automation

• Explore and adopt AI-assisted tools (e.g., copilots, automated triage) where they can improve efficiency and quality

• Contribute to refining how these tools are used in practice, based on real-world support needs

Navigate Regulatory and Compliance Contexts

• Develop a working understanding of relevant compliance and regulatory requirements (e.g., KYC/AML, payments, basic securities concepts)

• Follow established guardrails for compliance-sensitive situations and escalate when needed

• Partner with internal teams (e.g., Legal, Compliance) when issues touch regulated workflows

Note: Prior fintech or regulatory experience is not required, you’ll ramp on this as part of the role.

Collaborate Cross-Functionally and Advocate for Customers

• Partner closely with Engineering to escalate technical issues with clear, actionable context

• Work with Product to surface recurring issues and customer pain points

• Help ensure that patterns from support are visible and actionable, not just resolved individually

Deliver High-Quality Customer Communication

• Communicate clearly and professionally with both technical and non-technical users

• Explain issues and resolutions in a way that builds trust and clarity

• Handle escalations with ownership, composure, and attention to detail

What You'll Bring

Required

• 2–5 years of experience in technical support, support engineering, QA, or a similar customer-facing technical role

• Strong troubleshooting skills, comfortable working with:

  • Logs and error messages

  • APIs

  • Basic SQL (or willingness to learn)

• Ability to think in systems, not just solving issues, but identifying patterns and opportunities for improvement

• Strong written and verbal communication skills

• High ownership mindset with the ability to manage multiple priorities effectively

• Customer-focused approach with attention to detail and follow-through

Nice to Have

• Experience with support or project management tools (e.g., Intercom, Zendesk, Jira, Linear)

• Familiarity with monitoring or APM tools

• Exposure to payments, fintech, or compliance-driven environments

• Interest in improving workflows through automation or AI tools

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 [email protected]. 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.