rickb.dev

Rick Benavidez

2026
May 2018 – Present

LEANSTACK

Co-Founder

  • Joined Ash Maurya (best-selling author of Running Lean) to transform existing entrepreneurship education app into a comprehensive "accelerator-in-a-box" platform, adding cohort management, founder portfolio tracking, and structured learning paths that guide entrepreneurs from concept validation through product-market fit.
  • Built AI coaching agent to support business idea development and model validation. Designed chat-based UX for complex multi-step workflows. Implemented evaluation, observability, and testing strategies; optimized token usage/costs, and integrated customer feedback.
  • Own all technical architecture, infrastructure, and design/UX decisions, building Ruby on Rails backend with advanced JavaScript front-end to deliver intuitive experiment tracking and customer discovery workflows.
  • Coach dozens of startup founders and enterprise innovation teams through structured framework sessions, bridging technical product decisions with customer development methodology.
2018
Mar 2017 – May 2018

PhishMe (Cofense)

Software Engineering Manager

  • Managed a team of 8+ engineers across multiple scrum teams in cybersecurity SaaS environment, maintaining accountability for software delivery and sprint velocity.
  • Guided team through 3 major architecture transitions while maintaining zero-downtime deployments and backward compatibility for enterprise customers.
  • Built remote-first team culture supporting career growth through structured coaching, goal-setting, and technical mentorship across multiple time zones.
2017
Sept 2015 – Mar 2017

Student Loan Genius

CTO

  • Built engineering organization from the ground up: hired and supported a 6-person team, established coding standards, implemented full software development workflow and CI/CD pipelines.
  • Achieved ISO 27001 certification and implemented ISMS, enabling enterprise sales and unlocking partnerships with Fortune 500 companies.
  • Represented company in technical due diligence, customer security reviews, and RFP responses, directly contributing to close of key enterprise deals.
2015
May 2013 – Sept 2015

Communication Service For The Deaf

Director of Software Development

promoted from Sr. Software Engineer → Manager

  • Led development of first-of-its-kind national online marketplace connecting deaf and hard-of-hearing community to sign language interpreters, managing product evolution from private beta through public launch.
  • Managed and grew team from 3 to 12 engineers, establishing sustainable development practices in HIPAA-regulated environment.
  • Drove technical decisions on WebRTC implementation for video interpreting, handling real-time communication challenges across variable network conditions.
2013
Jun 2008 – May 2013

ActiveProspect

Sr. Web Developer

  • Contributed to bootstrapped B2B SaaS platform serving lead generation space, supporting growth from startup through established business with 200+ enterprise customers.
  • Led development of 3 products from initial concept to production: a lead validation API, consent management system, and analytics dashboard.
  • Patent #11610182 for work on an electronic lead verification system.
2008
2000 – 2008

Early Career

Web Developer & Systems Integration Specialist

  • Web engineering and systems integration roles at Strategic Forecasting (geopolitical intelligence), Mindshare Interactive (non-profit digital agency), EdgeCloud (consulting), and early-stage startups. Experience includes Python, PHP, Perl, MySQL, Drupal, and WordPress development.

Skills

Languages & Frameworks Ruby, Ruby on Rails, JavaScript/TypeScript, Hotwire (Turbo/Stimulus), React, HTML/CSS, TailwindCSS
Infrastructure & Tools AWS, Heroku, Render, Cloudflare, Linux, PostgreSQL, MySQL, Redis, MongoDB, Git, CI/CD, Sentry, AppSignal
AI & LLM Integration Production AI Agent Development, LLM API Integration, RAG, Evaluation Frameworks, Prompt Engineering & Token Optimization, AI-Focused UX Design
Product & Process Continuous Innovation, Agile/Scrum/Kanban, Lean Startup, Jobs To Be Done, User Research, MVP Development
Leadership Team Building, Remote Team Management, Career Coaching, Technical Mentorship, Cross-functional Collaboration
Security & Compliance ISMS, ISO 27001, HIPAA, Security Audits, Compliance Documentation

Education

St. Mary's University of San Antonio, Texas

B.A., English — Minor in Computer Science

2000