Josh Rathke

About Josh Rathke

I\'ve spent the last 5+ years building an engineering organization from the ground up at TryNow — not just the technology, but the culture, principles, and growth paths that make a team self-sustaining. I think of engineering leadership like coaching: my job is to put people in positions where they\'re stretched but supported, and to build systems that grow engineers into leaders. I\'ve stayed technical enough to lead architecture decisions while staying off the critical path, and I\'ve operated across the full stack in ecommerce, healthtech, and defense-adjacent communications infrastructure.

Experience

1. Head of Engineering

   Trynow.Com

   Oct 2020 — Present

   Hired 20+ engineers over 5 years, coaching and mentoring 6 through various promotions while maintaining a team that scaled the platform from MVP to 100+ merchants processing $55M in deferred payments annually.Organized engineering into 3 teams of 4 (platform infrastructure, core product, and partner integrations), enabling each team to build deep domain expertise.Made the deliberate decision to restructure the codebase for consistent patterns and abstractions specifically to maximize AI tooling effectiveness, accepting short-term velocity loss for more consistent, manageable AI-assisted output.Introduced AI workflows for project planning and story writing, reducing engineer time spent on documentation by roughly 80% and redirecting that capacity toward product work and value creation.Built a real-time data insights pipeline serving 100+ merchants with actionable metrics (Net AOV, conversion rates, LTV, ROI) that previously didn\'t exist, delivering it off the critical path to avoid blocking the team.Co-developed Shopify\'s Try Before You Buy APIs as one of their first TBYB partners, enabling any Shopify merchant to integrate Try Before You Buy into their storefront.Shipped TryNow\'s core Shopify app after 2 rejections and 4 complete rewrites driven by Shopify\'s evolving requirements, ultimately delivering the checkout integration that enabled every transaction on the platform.Built an AI-powered monitoring system that detected merchant issues in near real-time, enabling the team to respond before merchants were impacted.Shipped a production MCP server with OAuth 2.0, enabling both internal teams and merchants to automate workflows through AI tooling.

Education

• Purdue University

  Bachelor of Science, Computer Graphics Technology

  2007 — 2011

Skills

• Microsoft Office
• Management
• Nonprofits
• Wordpress
• Angularjs
• Html Scripting
• Css
• Wireless Networking
• Volunteer Management
• Jquery
• Php
• IT Management
• Volunteer Recruiting
• Systems Analysis
• IT Strategy
• IT Infrastructure Design
• IT Infrastructure Management