Chris Macomber

Startup Executive & Product Leader

I build and scale product organizations that transform customer insights into business impact. With experience founding startups and leading teams at companies from early-stage to enterprise, I specialize in AI-powered products, B2B SaaS, and creating cultures of ownership and collaboration.

San Mateo, CALinkedIn

Experience

CaaStle logo

Global Head/VP of Product and Design

CaaStle·Mountain View, CA
2023 - 2025
  • Led and scaled the product function comprising a global team of 25+ PMs and UX designers covering B2B, B2C, Data Science/AI, mobile, web, and logistics experiences
  • Transformed the product department into a customer insights and business impact engine through agile research, KPI ownership, AI tools, and evolved prioritization frameworks
  • Launched patented AI features for eCommerce discovery, pricing projections, and image/copy generation leveraging GenAI, DiffusionAI, machine learning, RAG, and LLMs
  • Evolved internal PDLC process by combining human oversight and AI agents across product, design, and engineering teams
  • Delivered compelling value: increased gross margin by 20%, reduced liquidation inventory by 75%, and reduced returns by 33%
WhoKnows logo

CEO and Founder

WhoKnows·San Mateo, CA
2012 - 2023
  • Built patented AI that enriched 370M real-time profiles with multi-channel campaigns and lead gen services to build agile growth engines for B2B startups
  • Launched beta of the first AI Marketer that can compose, optimize, and scale full marketing sequences with automated testing
  • Grew the team from 2 to 50 including hiring the leadership team that built their own departments
  • Created a growth engine generating $2.5M ARR with an LTV/CAC ratio of over 4x
  • Raised over $8M from Intel Capital, PivotNorth, SVDC, and multiple angel groups
  • Led the company through multiple pivots and reached profitability in 2023
Lytro logo

Director of Product Management

Lytro·Mountain View, CA
2011 - 2012
  • Lytro disrupted the $40B camera market with innovative light-field features and re-invented the point-and-shoot camera experience
  • Led team of Product Managers to build Lytro's first end-to-end product experience including web, mobile web, mobile app, desktop software, and social
  • Balanced voice of customer feedback, product and viral loop analytics, market trends, and product instinct to establish strategy and priorities
  • Led biz dev efforts for deeper integration with all major social networks and photo-sharing sites
Reputation.com logo

Principal Product Manager

Reputation.com·Redwood City, CA
2009 - 2011
  • Led team of product managers and UX designers responsible for the company's reputation offerings
  • Launched first freemium offering with 3x conversion rate improvement over previous experience
  • Launched Facebook app in two weeks to help manage Facebook privacy settings
  • Improved monthly retention of MyReputation by 50% over 6 months by adding more recurring value
  • Established Net Promoter survey, customer council, analytics, and A/B testing disciplines
Intuit logo

Product Manager, QuickBooks Online

Intuit·Mountain View, CA
2009 - 2010
  • Responsible for monetizing QBO from acquisition to conversion via agile marketing techniques
  • Drove 3x improvement in new users acquired and 33% improvement in trial conversions
  • Redesigned first-time use experience which halved the time to value for new users
Intuit logo

Product Manager, Intuit Community / JumpUp

Intuit·Mountain View, CA
2007 - 2009
  • Led team of PMs and UX designers to combine all of Intuit's small business forums into one community
  • Led team to embed community directly into QuickBooks 2009 and Intuit.com (Live Community)
  • Converted Live Community widget into a platform for all of Intuit's offerings and external partners
  • Grew the # of users 4x over 6 months using SEO, marketing, and new features
  • Managed the Just Start social campaign (won the Warrillow award for best small business campaign)
Intuit logo

Product Manager, QuickBase

Intuit·Mountain View, CA
2006 - 2007
  • Designed and launched the QuickBase Application Library, a user-contribution repository of solutions to increase trial conversion rates
Cisco Systems logo

Group Engineering Manager, eLearning Application Development

Cisco Systems·San Jose, CA
2003 - 2005
  • Managed and led the engineering department for Cisco's entire e-learning application portfolio
  • Platform supported over 1M students in 150 countries
  • Created development and project management processes for cross-functional, international teams
Sapient logo

Manager, Technology

Sapient·San Francisco, CA
1997 - 2003
  • Led multiple, international development projects as project manager and architect for global corporations

Education

MIT Sloan School of Management logo

Masters

Masters in Business Administration

Grad 2007
    Stanford University logo

    Bachelors

    Stanford University·Palo Alto, CA

    Bachelors in Computer Science

    Grad 1997

      Portfolio

      Vibe Startup Lab homepage with feature cards

      Vibe Startup Lab

      A platform designed to help entrepreneurs and startups accelerate their journey from idea to product-market fit. Features include a structured methodology for validating startup ideas, a directory of professionals to help with various tasks, curated tools and resources, task management for each startup phase, and a community of founders collaborating on their ventures.

      StartupEntrepreneurshipCommunity+2
      Wrollo homepage with network visualization

      Wrollo

      A networking platform that makes it easy for your network to help you by emailing your message to their matching contacts, retweeting your tweets, and liking your LinkedIn posts. Features include network request management, contact filtering with 37K+ contacts, message templates with personalization, and analytics to track your extended network reach.

      NetworkingSaaSB2B+2
      Alucify.ai dashboard

      Alucify.ai

      An AI-powered platform that leverages cutting-edge machine learning to provide intelligent solutions for businesses. Features advanced analytics, automation capabilities, and seamless integrations.

      AIMachine LearningSaaS+1
      VS Code extension screenshot

      VS Code Extension - Code Assistant

      A powerful VS Code extension that enhances developer productivity with intelligent code suggestions, automated refactoring tools, and seamless integration with development workflows.

      VS CodeDeveloper ToolsTypeScript+1
      Workflow automator extension

      VS Code Extension - Workflow Automator

      Streamline your development process with this VS Code extension that automates repetitive tasks, manages project configurations, and integrates with popular CI/CD pipelines.

      VS CodeAutomationCI/CD+1