Software Development Manager, Observability Platform

About the role

Join Wealthsimple as the founding Software Development Manager for our Observability Platform team. You will build and lead a team responsible for making our production systems transparent and understandable for all engineers and AI agents. This role is central to shaping how Wealthsimple monitors and operates its technology for years to come.

Key facts

What you'll do

Lead, mentor, and develop a team of engineers, fostering a culture of technical excellence and continuous improvement.

Define the long-term strategy for Wealthsimple's observability capabilities, aligning engineering efforts with leadership vision.

Develop foundational data models and standardized instrumentation using OpenTelemetry to ensure rich telemetry is the default.

Drive improvements in system reliability and reduce mean time to resolution by focusing on customer experience signals and service level objectives.

Build infrastructure that supports AI-driven incident investigation and operational tooling, enabling fast, high-cardinality data access.

Execute a test-and-learn approach, validating new concepts with pilot teams before broad rollout.

Strategize on build, buy, and broker decisions for observability tools, balancing value, cost, and vendor lock-in.

Contribute hands-on to architecture, code, and design reviews to unblock teams and prototype new solutions.

Requirements

A minimum of 7 years in software development, with a focus on building platforms, and at least 3 years in engineering management.

Demonstrated experience in creating or implementing an in-house observability platform, including structured event data, high-cardinality data, sampling, and context propagation.

A proven track record of delivering developer SDKs and libraries, with practical application of OpenTelemetry or similar standards, and experience with SLI/SLO design.

Strong strategic and technical leadership skills, with the ability to set a vision, manage experimental initiatives, remain hands-on with architecture, and influence across different teams.

Evidence of successful people management, including coaching, talent retention, and building inclusive, high-performing teams.

Nice to have

Experience in the fintech or other regulated industries.

Familiarity with Kubernetes, Argo Rollouts, or ClickHouse.

Experience with observability for LLM or AI agent workloads.

Skills & tools

OpenTelemetry

Datadog

Claude Code

LLMs

Open standards

SLOs

SLIs

Wide-event data models

High-cardinality data

SDKs

Libraries

Practical notes

This is a full-time, remote position based in Canada. Wealthsimple offers comprehensive health benefits, life insurance, long-term group savings with employer match, 20 vacation days, 4 wellness days, unlimited sick and mental health days, and a 90-day remote work option outside of Canada. The company is committed to diversity, inclusion, and accessibility in its hiring process. AI tools may be used to support application review, but all final hiring decisions are made by people.

About the company

Wealthsimple Inc. is a Canadian online investment management service. The firm was founded in September 2014 by Michael Katchen, Brett Huneycutt, and Rudy Adler. The company is based in Toronto. As of October 2025 the firm holds over C$100 billion in assets under administration. The business operates as a digital platform that provides automated investing services and financial products to retail clients. It focuses on lowering barriers to entry for individuals seeking to build long-term wealth. The platform uses technology to manage portfolios and offer financial advice at scale. The firm is primarily owned by Power Corporation. Power Corporation holds a 52.4 percent undiluted stake aggregated through three entities. These entities include its wholly owned subsidiary Power Financial and its majority owned subsidiary IGM Financial. The stake also includes its controlled alternative asset platform Sagard's Portage Ventures. This ownership structure provides the company with significant institutional backing. Wealthsimple continues to expand its range of financial services within the Canadian market. The company aims to make sophisticated financial tools accessible to a broad audience. It competes with traditional banks and other fintech firms by emphasizing user experience and low fees. The leadership team remains focused on product development and client growth.