How staff engineers approach leading remote teams with Cassia Scheffer from Wealthsimple

What’s the right way to operate as a hybrid team in today’s engineering landscape?

In this episode of the Distributed podcast, Jack Hannah speaks with Cassia Scheffer, Staff Software Engineer at Wealthsimple, to explore her best practices for mentoring and collaborating in a remote-first environment. Cassia shares insights on balancing hybrid work cultures, the power of pair programming, and how distributed ownership empowers engineers to make better decisions. She also reflects on the challenges of feeling disconnected in hybrid setups and how Wealthsimple prioritizes customer-focused values to align teams.



Highlights:

• The importance of balancing hybrid work cultures to foster a sense of belonging
• How schema validation enables distributed ownership and better decision-making
• Why mentoring and pair programming improve collaboration and learning
• Strategies for driving alignment through clear documentation
• The role of curiosity in planning, problem-solving, and building strong teams

In this episode, we cover:

(00:00) – Kicking Things Off With Cassia Scheffer

(00:45) – Wealthsimple’s Hybrid Model and Remote-First Approach

(02:38) – Why Pair Programming is Essential for Remote Engineering

(04:56) – How Wealthsimple’s 400-Person Engineering Team Stays Aligned

(06:58) – Scaling Communication: From Growing Pains to Real-Time Decision Making

(10:18) – A Leadership Crisis and the Culture Clash That Followed

(13:48) – How Hybrid Work Creates Visibility and Belonging Challenges

(19:00) – API Platform Engineering: Driving Adoption Across 30 Teams

(30:42) – Coaching Engineers: Pairing as a Tool for Growth and Problem-Solving

(38:52) – Final Takeaway: Curiosity as the Key to Effective Collaboration

Referenced:

Organizational Culture and Leadership by Edgar H. Schein: https://www.amazon.com/Organizational-Leadership-Jossey-Bass-Business-Management/dp/1119212049

Where to connect further:

Connect with Cassia Scheffer on LinkedIn

More about Cassia on her website

More about Wealthsimple

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Connect with Jack Hannah