Senior Software Engineer (Developer Experience)

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 [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.