Compensation: Annual salary + Performance-based + Bonus
Why Upgraded?
We’re building what you might call the Bloomberg Terminal for Startups or the App Store for AI Work—a platform that doesn’t just advise, but automates the discovery, qualification, drafting, and submission of grants, tax credits (like SR&ED), subsidies, all with minimal overhead and maximal impact.
Upgraded helps high-growth tech startups unlock an average of ~$104k/year in savings, close to without lifting a finger. That's possible because our AI and automation uncover funding opportunities missed by human teams. Our promise? If we don’t deliver results, clients don’t pay.
What You’ll Own
As an AI & Automations Engineer, you will build the plumbing, the “agent-layer”, and the real time systems that make our vision possible. You’ll:
● Design & build pipelines that ingest client data (financials, engineering logs, time sheets, product roadmaps, etc.), validate eligibility for funding programs, map to relevant criteria (e.g. SR&ED technical uncertainties, expenditures, etc.), and prepare draft submissions.
● Develop automation agents / microservices that generate narratives, supporting documents, estimate costs, track documentation, and prepare audit-ready artifacts.
● Integrate with external APIs / SaaS tools (accounting, payroll, project management, etc.) so our system can pull data continuously, flag anomalies, and drive insights.
● Optimize AI / ML models for grant eligibility scoring, narrative drafting, and quality prediction. Help monitor performance, error rates, and feedback loops.
● Ensure compliance & reliability: audit trails, versioning, rigorous testing (unit/integration), error handling, data security, privacy.
● Collaborate closely with product, operations, and strategy teams to prioritize automation features that deliver the most leverage (e.g. fastest time to funding, reduction in manual labor, fewer audit rejections).
What You Bring
● Strong software engineering experience, ideally with AI / ML, automation / orchestration, or data pipelines.
● Comfortable with Python / Typescript / JavaScript / or other language(s) used in automation / AI workflows.
● Experience with working on systems that need to produce high-quality text (narratives, reports) as output; bonus if you’ve built or fine-tuned models or prompt pipelines.
● Understanding of SR&ED or similar R&D tax/incentive programs is a big plus (or demonstrated ability to learn fast in regulated environments).
● Experience integrating multiple data sources—accounting systems, payroll, project management, time tracking, etc.
● Strong focus on engineering discipline: testing, monitoring, error handling, security, and versioning.
● Autonomy + collaborative spirit. You own features end-to-end, but you also align closely with product and strategy.
● Clear communicator. Able to explain technical tradeoffs to non-technical stakeholders.
Why This Role Excites
● You’ll build tools that directly enable innovation funding for dozens or hundreds of startups, helping them avoid dilution and scale faster.
● You’ll work in “founder mode” with Will Richman—someone who has shipped, scaled, exited, and is now stacking AI + automation into infrastructure.
● Massive leverage: one good automation you build could save hundreds of hours, prevent audit rejections, or unlock tens-of-thousands in grants per client.
● Opportunity to shape the AI stack (narrative generation, eligibility prediction, automation agents) from early stages—there’s little technical debt, lots of greenfield.
Stand-Out Move
Send us a project or sample: anything you’ve built that involves automation, data pipelines, or generating text (even scripts, dashboards, bots, etc.).
Also, 1-2 paragraphs: How would you design an automated AI & automations pipeline that goes from raw product dev / engineering work to client ready to use, delivered AI & automations?
Apply Now
If you’re energized by the convergence of AI, automations, the future of work, grant funding, and growth strategy—and want to design the way startups thrive—let’s chat.
Email your resume + sample deliverable to careers@getupgraded.ca, or apply at getupgraded.ca/careers. Help build the bridge between AI systems and startup-scale innovation.
