openashbyhqbaincapitalventures
People Systems & Automation Specialist
Relay Financial
LocationToronto, ON
WorkplaceHybrid
EmploymentFullTime
Posted2026-03-23T22:50:29.072+00:00
Last observed2026-06-24 08:29:10.902639
Job idbaincapitalventures-relay-financial:ashbyhq:b80cea75-2bae-45b4-9171-218c983d30f8
Relay is a digital banking platform that gives self-made business owners the tools and know-how to be great with money—bringing clarity, confidence, and control to every dollar earned, so they can turn hard work into lasting success. We do this by replacing financial guesswork with real visibility, transforming cash flow from a constant source of stress into a clear signal owners can use to run stronger, more resilient businesses. THE MISSION Our People Team exists to build Relay into a company high-performing, ambitious people actively choose and a place where they do career-defining work. We are hiring a People Systems & Automation Specialist to build the technical infrastructure that makes that possible at scale. This is a 12-month contract. The mandate is clear: automate the automatable, streamline the rest, and leave the People team operating at a fundamentally different level of efficiency. If there is still meaningful work to do at the end of the year, we can consider contract extension or potentially a conversion to full time. The Problem Statement Right now, our People tech stack is fragmented. Data lives in multiple systems with limited connectivity, manual handoffs fill the gaps, and there is no single source of truth for People data. That is the problem this role exists to solve. Not by adding process, but by eliminating it. WHAT YOU'LL BE DOING The primary areas of ownership in this role include, but are not limited to: Process Mapping & Automation Strategy - Map every People process end-to-end: Onboarding, offboarding, employee changes, benefits enrollment, performance cycles, etc, and document the current state with clear eyes. - Identify what can be fully automated, what needs a human in the loop/lead and why, and what is manual today only because no one has built the solution yet. - Build a prioritized automation roadmap and own delivery against it. - Evaluate workflow automation and integration platforms, make a recommendation on what our team should adopt to best achieve our goals, and implement it. Systems Integration & Infrastructure - Own our full People tech stack: HRIS, ATS, onboarding, employee experience, and benefits tools with a mandate to make them work together. Our current tech stack contains: Rippling, Gusto, Ashby, CultureAmp, Notion, Google Suite, Claude, ChatGPT, Jira, and various benefits/insurance provider platforms. - Build and maintain integrations between systems using native connectors, automation tooling, and lightweight custom solutions where gaps exist. - Partner with IT to understand existing tools, surface underutilized capability, and ensure the People team can use what we have before we add anything new to our stack. - Bring People data into a data visualization tool (Snowflake or similar) so the team has a reliable, queryable data layer, and help build the integrations that get clean and correct data there automatically. - Own documentation on system configurations, integrations, and decisions (via Notion) so nothing lives only in your head. AI-Powered Workflows - Use AI tools actively and practically. Not as a novelty, but to automate recurring workflows, reduce manual reporting, and surface insights without human intervention. - Identify where AI can replace manual judgment in low-stakes, high-frequency People tasks and build those workflows. - Stay close to what is new in HR/People tech and AI tooling and experiment quickly. Data, Reporting & Analysis - Build and maintain a single source of truth for People data: headcount, attrition, compensation, engagement, and hiring metrics, and keep it accurate. - Build self-serve dashboards that give People Business Partners and leadership real-time visibility without coming to you for every pull. - Solve the data extraction problem for tools like CultureAmp. Figure out how to get that data into your reporting infrastructure reliably and automatically. - Once the data layer is clean, use it. Run analyses, surface trends, flag risks, an
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