People Operations Lead, Wealthsimple
Process Design
CA$116-146k
+ Equity
Senior and Expert level
Remote from Canada
Professional investing services made simple
Posted today
Professional investing services made simple
1001+ employees
FintechB2CPersonal financeInvestingFinancial ServicesSocial Impact
Posted today
CA$116-146k
+ Equity
Senior and Expert level
Remote from Canada
1001+ employees
FintechB2CPersonal financeInvestingFinancial ServicesSocial Impact
Company mission
To help everyone achieve financial freedom.
Role
Who you are
- 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
What the job involves
- 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
- 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
Our take
Wealthsimple is one of a crop of robo-advisors trying to democratise investment management. These companies are disrupting the industry by automating many of the processes involved in investment, removing the need for human advisors.
But while other so-called robo-advisors are focused on courting the high end of the market, Wealthsimple is trying to provide the same types of tools and advice to all users, regardless of the amount they have to invest.
Wealthsimple does have higher fees than some other robo-advisors such as Betterment and Charles Schwab. However, the company believes that it provides a more user-friendly platform, tailored to millennials who will be attracted to Wealthsimple due to its ease of use and social impact offerings.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
Top investors
-10% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
Oct 2025
$391.4m
LATE VC
May 2021
$533.8m
LATE VC
Total funding: $1.2bn
Company benefits
- Retirement savings matching plan through Wealthsimple Work
- Company equity for full-time employees
- Access to Premium Client perks, including personal finance learning & advice and a boosted interest rate on deposits
- Paid parental leave (6 months topped up to 100% of salary)
- 20 vacation days per year
- 90 Days Away program
- Top-tier health benefits
- Life & disability insurance
- Generous sick and mental health days
- Employee resource plan including services like RMT, psychology, and physiotherapy
- Up to $5,000 per year for mental health supports
- Gender Affirmation benefits
- Up to $1,500 per year for professional development
- Up to $1,500 per year for wellness and home office expenses
- Employee resource groups
- Social impact hours
Company HQ
Fashion District, Toronto, ON
Leadership
Michael Katchen
(Co-Founder & CEO)Previously worked as a Business Analyst at McKinsey and then at Ancestry.com as Country Director for Canada.
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