--- title: 'Senior Software Engineer (Developer Experience) at DealMaker' canonical: 'https://feeny.ai/job/senior-software-engineer-developer-experience-dealmaker-toronto-7ff0qp7ez7c7' type: 'job' last_seen: '2026-09-16' --- # Senior Software Engineer (Developer Experience) at DealMaker - **Company:** DealMaker - **Location:** Toronto, Canada - **Employment:** full-time - **Work type:** hybrid - **Posted:** 2026-09-14 - **Last confirmed live:** 2026-09-16 - **Apply:** https://jobs.ashbyhq.com/dealmaker/a4fc28cb-94bd-44a3-83bc-199d9b48580c ## Job 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. ## Who You Are DealMaker is building the infrastructure behind online capital raising. Our engineering org is investing heavily in AI across the development lifecycle, from how code moves through review to how developers get a working environment. This role owns a meaningful slice of that investment: the tooling, harnesses, and environments that make every other engineer faster and more confident in their changes ## What You'll Do AI in the engineering lifecycle - Automate the PR-to-merge path: define what "good" looks like and use AI to remove manual steps. - Improve the quality of AI-generated QA plans and measure how well they actually cover our changes. - Build evaluation coverage for AI-powered product features so a prompt or tool change can't ship without passing a graded test set. - Track what each AI workflow costs and which model or tool it should be using. - Maintain our internal AI workflow library: retire overlap, cut what's unused, improve what stays. Testing risky paths - Build test harnesses for scenarios that are hard to set up manually, like email delivery or investor checkout. - Cut test wall-clock time by running only the tests a change actually affects, and report the time saved. Developer and agent environments - Deliver isolated local environments (macOS and Linux) so a developer can run two changes at once without collision. - Cut cloud coding-agent startup from minutes to seconds; make targeted test runs and linting reliable in those environments. - Work out how credentials and network access get provisioned for agent environments, including where a vendor can't yet do it securely. Measuring developer experience - Define the small set of numbers we manage to (e.g., time-to-first-shipped-change for new hires, local environment reliability, CI duration, flaky-test count), instrument them, and report monthly. What Skills You Need - Strong hands-on engineering background with CI/CD, developer tooling, or testing infrastructure, you've built and shipped this kind of thing, not just used it. - Self-starter who drives initiatives on their own. This is a small team, so you'll set your own roadmap and work directly with engineers across the org to get buy-in. - Practical experience using AI tools inside a real engineering workflow (coding agents, AI-assisted QA/eval, prompt-driven automation), with concrete examples of what worked and what didn't. - Comfort defining a metric, instrumenting it, and using it to drive a decision. - Judgment for cost/quality tradeoffs on tools and models, this role reviews and changes what the team spends on AI, not just what it uses. - Bias to build the smallest thing that removes the manual step, not the most complete framework. 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. ## About DealMaker ## Company Overview - **One-liner**: DealMaker provides an all-in-one digital platform that enables companies to raise capital online via Regulation A, Regulation Crowdfunding (CF), and Regulation D offerings, handling everything from investor acquisition to compliance and payments. - **Entity Type**: Private (multiple venture rounds, latest private equity round in 2024) - **Headquarters**: New York, New York, United States - **Founded**: 2018 - **Founders**: Rebecca Kacaba (CEO & Co-Founder) ## Core Business - **Primary industry**: Financial Services / Capital Markets Technology (Fintech) - **Target customers**: B2B – growth-stage companies, startups, and established organizations looking to raise capital from retail and institutional investors. - **Mission/purpose**: Empower founders to raise capital digitally from their own communities and through strategically marketed campaigns, making online capital raising mainstream. ## Products & Services - **DealMaker Platform (SaaS)**: End-to-end capital raising solution that provides investor acquisition, securities management, fund processing, and investor communications in one system. Acts as a one-stop-shop digital raise platform, transforming the process into a simple eCommerce experience – companies add an “Invest Now” button to their existing site and DealMaker handles compliance, payments, and everything in between. ## Market Standing - **Valuation/Market Cap**: Not disclosed (privately held) - **Key Metric**: Annual Revenue of ~$9.0 million (latest estimate); total capital raised for clients exceeds **$2 billion** (including notable clients like Green Bay Packers, Miso Robotics, Monogram Orthopaedics). - **Notable Investors/Partners**: CIBC Innovation Banking (led venture rounds in 2022 & 2023), The Canadian Securities Exchange (investor in 2022 round), and additional private equity investment (2024). - **Growth Signals**: Headcount grew 37.9% year-over-year to 143 employees; operates in 8 countries; acquired Rally On Media (2025) and Ridge Growth Agency (2022); active job postings for roles in sales, client strategy, and creative production. ## Competitive Advantages - **One-stop shop**: Integrates investor acquisition, securities management, compliance, and payments – eliminating the need for multiple vendors. - **Proven track record**: Helped raise over $2 billion for hundreds of companies, including high-profile names. - **Simplified user experience**: Capital raising is reduced to a single “Invest Now” button, drastically lowering friction for founders. - **Regulatory expertise**: Handles complex SEC regulations (Reg A, CF, D) and provides built-in compliance capabilities. ## Strategic Focus - **Current priorities**: Deepening marketing capabilities (acquisition of Rally On Media), expanding enterprise and partnership sales (Enterprise Account Manager, Director of Client Strategy roles), and growing the technology team to enhance platform features. - **Direction**: Scaling the platform to serve larger, more complex raises while maintaining the self-serve eCommerce model; increasing international presence (offices in US, Canada, Colombia, Brazil, Nigeria). ## Why Work Here - **Culture highlights**: The careers page describes an environment where “ideas flow freely, innovation is rewarded, and excellence is the standard.” The team is mission-driven, focused on making capital raising accessible. - **Location & hybrid policy**: Offices in New York (HQ) and Toronto, with team members across the Americas. Remote/hybrid details not explicitly stated; likely hybrid given multiple office locations. - **Engineering & team**: Tech stack includes Python, Django, React, Snowflake, dbt, and modern tools. Employees come from companies like Republic, StartEngine, and Strikepoint. - **Note**: Employee rating on LinkedIn is 2.7/5.0 (61 reviews), with below-average scores in work-life balance (2.1) and culture (2.3) – job seekers may want to investigate further. ## Sources 1. [dealmaker.tech](https://www.dealmaker.tech/) 2. [dealmaker.tech/about-us](https://www.dealmaker.tech/about-us) 3. [linkedin.com/company/dealmakertech](https://www.linkedin.com/company/dealmakertech) 4. [theorg.com/org/dealmaker](https://theorg.com/org/dealmaker) 5. 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