Sam Swanke

Engineering leader with Amazon and startup CTO experience. At Amazon, delivered platforms enabling nine-figure insurance contracts and supporting hundreds of nonprofit partners processing tens of thousands of annual cases. As CTO, led a zero-downtime AWS migration while contributing significant code - dramatically improving API performance and operational stability. Deeply invested in growing engineers: coached multiple promotions at Amazon, developed a non-technical hire into an effective engineer, and retained the entire team through a demanding rebuild. Combines distributed systems depth with a leadership style that elevates people and ships results.

HelloPrenup

Chief Technology Officer

Dec 2024 - Present | New York, NY

Built and led the engineering team at an early-stage (20 person) legal technology company, owning hiring, architecture, and delivery of customer-facing distributed systems.

  • Built the engineering organization from zero, hiring and onboarding 4 engineers; retained 100% of the team through a high-pressure 9-month platform rebuild
  • Owned the full hiring funnel, sourcing and screening from 300+ candidates across phone, technical, and onsite rounds hiring top talent within tight budget constraints
  • Coached a non-technical employee into an effective junior engineer on track to reach mid-level; created performance guidelines and calibrated each engineer against clear expectations
  • Reduced new-hire time-to-productivity to 2 weeks through structured onboarding and comprehensive system documentation, even during a full platform rebuild
  • Led migration from a monolithic no-code platform to a stateless, horizontally scalable AWS architecture; executed zero-downtime cutover while maintaining uninterrupted customer service for 5-10k monthly active users
  • Delivered production launch handling 8M+ monthly requests with 130ms average response times; contributed 30% of code changes while establishing durable architectural patterns
  • Reduced customer support tickets by 44%, improved page load times by 61%, and reduced API response times by 91% through architectural and performance improvements

Amazon

Software Development Manager

May 2022 - Dec 2024 | New York, NY

Led a team of 8 (5 direct-report SDEs, 1 Sr. SDE, 1 PM-T, 1 TPM) building large-scale, highly reliable internal platforms for Amazon Treasury's Global Risk Management & Claims organization, partnering with product, finance and claims teams.

  • Took ownership of a mission-critical insurance request platform 4 weeks before launch following external vendor (ProServe) handoff; drove cutover plan, reprioritized scope, and delivered a stable production launch
  • Led structured handover deep-dive: triaged 65 issues, delivered 47 launch-critical fixes, including 33 bugs, 9 data-integrity gaps, and 5 configuration defects prior to go-live
  • Enabled procurement workflows supporting nine-figure insurance contracts by delivering a reliable, auditable system under aggressive deadlines
  • Designed and launched distributed case-management workflows supporting over 750 nonprofit partners and 30,000 annual cases, using AWS-native services and event-driven orchestration
  • Improved engineering quality and operational readiness: raised unit test coverage from 5% to 40%, introduced production readiness gates, and strengthened monitoring/alerting to reduce regressions
  • Reduced weekly on-call incidents by 50% through improved test strategy, better operational processes, and targeted architectural simplification
  • Managed and mentored 5 engineers; coached 2 engineers through successful L4 to L5 promotions and expanded ownership across system areas
  • Navigated shifting org priorities (including deprioritization of a flagship product) while maintaining team morale, delivery predictability, and customer trust

Amazon

Software Development Engineer II

Aug 2021 - May 2022 | New York, NY

  • Led architecture and implementation of a greenfield distributed service using AWS-native infrastructure, designing scalable data models and workflows for complex business processes
  • Served as front-end technical lead and mentor, carved a pathway to promotion into engineering management

Feather

Senior Software Engineer

Dec 2019 - Jul 2021 | New York, NY

  • Led development of internal tools streamlining operational workflows and reducing manual overhead
  • Improved site performance through targeted frontend optimizations, reducing load times by 30%

CALA

Software Engineer

Aug 2018 - Nov 2019 | New York, NY

  • Engineer #2 at a fashion technology startup; helped scale the engineering team and build core platform features supporting product design, production tracking, and fulfillment

Dealer.com

Software Engineer / Intern

May 2016 - Aug 2018 | Burlington, VT

  • Built data-processing libraries to canonicalize large-scale customer data and developed maintainable frontend applications in Java and Angular
  • Shared modern frontend best practices through internal technical talks

Cosechando Felicidad Inc

Front-End Engineer (Volunteer)

Aug 2015 - Present | Remote

  • Sole developer for HarvestingHappiness.org, supporting a nonprofit serving vulnerable communities through long-term volunteer engagement