Lead, People Operations - Process Design

Portage Ventures GP Inc.; United States; Hybrid; USD 140,000 - 210,000; Full time

Benefits offered by this job

Health benefits

Life insurance

Generous vacation & wellness days

Job summary

Wealthsimple is a Canadian fintech company redefining personal finance with simple, powerful products across investing, trading, crypto, and more. The People Systems & Operations team leads all employee lifecycle systems, workflows, and automation, driving reliability and scale as the business grows.

We’re seeking a senior professional to map complex processes, design AI-enabled workflows, and translate needs into technical specs for Workday and automation.

Qualifications

• 5+ years of experience in People Operations, HR transformation, or management consulting.
• Strong working knowledge of Workday and its data model.
• Practical fluency with AI tools and agentic workflows.
• Strong systems-thinking and facilitation skills.
• Ability to move between strategic framing and hands-on execution.
• Clear, concise written communication.

Responsibilities

• Map end-to-end workflows and eliminate friction.
• Diagnose bottlenecks and determine root causes.
• Define governance and scalable documentation standards.
• Translate business needs into Workday and automation specs.
• Lead change management and drive adoption.
• Establish metrics and post-launch dashboards.
• Collaborate with IT and analytics for data-driven automation.

Skills

People operations

Process mapping

HR transformation

Facilitation

Systems thinking

Stakeholder management

Written communication

Tools

Workday

Job description

Build something people love

Wealthsimple is Canada’s leading financial innovator. The company offers a full suite of simple, sophisticated financial products across managed investing, do-it-yourself trading, cryptocurrency, tax filing, spending and saving. Wealthsimple currently serves more than 4 million Canadians and holds over $155 billion in assets under administration. The company was founded in 2014 by a team of financial experts and technology entrepreneurs, and is headquartered in Toronto, Canada.

We're proud of what we've built — and we're just getting started. Read our Culture Manual and learn more about how we work.

About the People Systems & Operations Team:

The People Systems and Operations team builds and operates the systems, workflows, and automations the business runs on. We manage every stage of the employee lifecycle and own the design and optimization of the processes behind it. We're accountable for the reliability, scale, and integrity of our People systems.

We're looking for someone who can map broken processes in the morning and design workflows to enable AI and Automation as we scale. This role is the connective tissue between how our People team works today and how it needs to work to meet the growing demands and complexity of our rapidly scaling business.

You’ll lead process mapping and redesign across our highest-priority initiatives, while bringing an AI efficiency lens to every intervention. You’ll translate process realities from the ground floor into system requirements, identify where automation creates leverage, and help the broader People team to work differently. This is a consulting, project management, and hands‑on builder role all at once.

In this role you’ll have the opportunity to:

• Map & optimize end-to-end workflows: Lead current- and future-state process mapping across People initiatives to eliminate friction, reduce manual lift, and accelerate execution.
• Diagnose root causes: Challenge assumptions and help leaders distinguish whether a bottleneck stems from a process flaw, a systems limitation, or a change management gap.
• Establish scalable standards: Define documentation, handoffs, and governance frameworks so teams operate with consistency and low variability as Wealthsimple scales.
• Translate needs into technical requirements: Partner with our People Systems team to convert business challenges into actionable specs, identifying where AI agents, LLM tools, or native Workday workflows deliver the highest ROI.
• Apply practical AI judgment: Know the right tool for the job- distinguishing when a problem calls for AI leverage, standard automation, or simply process simplification.
• Define & track metrics: Establish baseline and target metrics (cycle time, throughput, error rates, cost savings) and build post-launch dashboards to ensure sustained adoption and measurable impact.
• Connect systems & data: Collaborate closely with IT, People Systems, and People Analytics to ensure all automations are built on solid data architecture and supported by tight feedback loops.
• Facilitate high-stakes alignment: Lead future-state mapping and design workshops across cross-functional groups- keeping discussions focused, driving key decisions, and securing clear ownership.
• Lead change management: Drive adoption through clear communication, helping teams clarify roles, build scalable habits, and navigate ambiguity during periods of change.
• Elevate AI capabilities: Raise the broader People team’s tech fluency through practical experiments, hands‑on learning, and shared tools.

Qualifications:

• 5+ years of experience in People Operations, HR transformation, process excellence, management consulting, or related fields within complex, scaling organizations, with a track record of redesigning cross‑functional processes.
• Strong working knowledge of Workday — not configuration ownership, but deep enough fluency in its data model, workflows, and capabilities that you can translate a process problem into a real Workday‑based solution and write requirements the Workday team can build from. You know what the system can and can’t do without needing to build it yourself.
• Practical fluency with AI tools and agentic workflows. You understand how AI agents are built - prompting, tool/function calling, system integration - well enough to design real solutions and prototype where useful, then scope and hand off cleanly to technical teams for production builds.
• Strong systems‑thinking capability, with the ability to connect strategy, operations, employee experience, data, and technology into clear and actionable recommendations.
• Strong facilitation skills: capable of running a workshop with skeptical stakeholders and arriving at a clear process map, agreed‑on requirements, and concrete next steps.
• Ability to move fluidly between strategic framing and hands‑on execution — you write the brief and do the work.
• Clear, concise written communication: you’ll regularly translate operational complexity into technical requirements and stakeholder‑ready narratives.

Why Wealthsimple?

Top-tier health benefits and life insurance

Long-term group savings with employer match, through Wealthsimple for Business

20 vacation days, 4 wellness days, and unlimited sick and mental health days per year

90 days away: work outside Canada for up to 90 days per year

Employee resource groups, including Rainbow (2SLGBTQ), Women of WS, and Black at WS

We are a hybrid team with over 1,500 employees across North America. The people are one of the best parts of working here: you'll collaborate with incredibly talented, curious, and driven teammates who are deeply committed to doing great work.

ICYMI

Technology & Innovation at Wealthsimple: We move quickly and build thoughtfully. That means we're always looking for better ways to work - whether that's new tools, AI, or rethinking how we approach a problem. We don't expect you to have all the answers, but we do expect curiosity and a willingness to evolve alongside the products we're building.

Inclusion Statement: We're building products for a diverse world, and we need a diverse team to do it well. We strongly encourage applications from everyone, regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.

Accessibility Statement: We're committed to an accessible hiring experience. If you need any accommodations throughout the interview process, please let us know - we'll work with you to make sure you have what you need. We also welcome any feedback on how we can better accommodate candidates with accessibility needs.

AI in Hiring: We may use artificial intelligence (AI) tools to support parts of our hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our team but don't replace human judgment – all final hiring decisions are made by people. If you have questions about how your data is used, reach out to us.