Jake Rudolph

Creating startups, software, communities, songs, and mental models

Led product, engineering, and design for Kindly, a B2B2C healthcare marketplace platform as the sole product builder and employee #1, working alongside the CEO.

Grew from no customers, experts or product to 5 committed pilot customers (4,000 employees), a team of 12 care experts and an end-to-end product with SOC 2 compliance in 90 days.

Hosting Socratica, a community of kind, ambitious people that meets weekly to make and share progress on our passion projects.

Rented out a hockey rink for Symposium, the world's largest student-run demo day with 80 projects and 2,500 attendees.

Supported by Anthropic, Shopify, and Velocity, with 40 global nodes.

Product Builder at Simple Ventures, a venture studio co-founded & backed by the top Canadian entrepreneurs like Mike Katchen Wealthsimple, Mike Murchison Ada, and Harley Finkelstein Shopify.

Built a comprehensive relational database and layer on internal tooling, dashboards, automations and CRMs for Alma Care, enabling the business to scale.

Architected the handbag subscription system and checkout flow for Zero Collective.

Explored the business case for new concepts in FinTech, Marketplaces and Health.

Studying Systems Design Engineering @ University of Waterloo.

Previously

Worked on value perception and recommendations at Outschool, a K–12 live online learning marketplace.

Quantitatively measured value perception, leading to micro-UI changes that boosted conversions and a macro-strategy deck for a new product line.

Identified through user reactions and bookings data that the recommendations feature was underperforming, leading to a full revamp of how the platform surfaces classes.

Led an end-to-end navigation research project at D2L which uniquely included assistive technology users (screen readers, voice navigation, etc.), B2B users and <16 y/o users.

First co-op at Sun Life. Beyond my assigned project, I self-initiated 3 projects, starting with discovery interviews to identify team pain points, which then led to redesigning a legacy tool and developing automations.

Joined Prequel as an early employee while still in high school, owning customer experience and operations leading to an acquisition.

I worked my first job as a basketball coach at 13 through to the end of high school.

In my senior year of high school, I coached a competitive rep team as the youngest registered Head Coach in Ontario.