About Me

Andy Woods

I'm Head of Product at DualEntry, the ERP built from the ground up to solve what legacy systems can't. We're the first AI-native ERP built after ChatGPT — designed for how finance teams actually work today, not retrofitted for it. I lead our product management, design, and education functions, and I'm fired up about what we're building alongside a team backed by Khosla Ventures and Lightspeed, who co-led our $90M Series A, with GV (Google Ventures), Contrary, and Vesey Ventures.

Previously, I spent 8.5 incredible years at Cockroach Labs, where I helped scale CockroachDB from pre-revenue to $100M+ ARR and category leadership. I led cross-functional teams of 50+ driving our Application and Database Ecosystem, pioneered our evolution into the AI-powered application stack, and owned CockroachDB's integration with the broader application ecosystem — observability, disaster recovery, change data capture (CDC), streaming, and migration workflows across hybrid and cloud environments. I also led pricing and packaging strategy, aligning product value with business outcomes through a data-driven, iterative approach to product-market-price fit.

I started this site to share insights at the intersection of AI, finance, and infrastructure. I explore how AI is transforming the systems businesses run on — and how we can build better products with these technologies.

Background

I have 15+ years of hands-on product development and people leadership, a Kellogg MBA (analytics, finance, marketing), and consulting-grade rigor. I specialize in turning ambiguity into scalable, margin-enhancing products that users love and businesses trust.

Subject Matter Expertise

  • AI-native product development: LLMs, RAG architectures, vector databases, and production deployment
  • Enterprise B2B user journeys across SaaS, open-core, and enterprise licensing models
  • Go-to-Market (GTM): product-led growth (PLG/PLS), sales-assisted motions, and field sales enablement
  • Finance and ERP workflows: how modern finance teams actually operate, from startups to public companies
  • Distributed infrastructure and databases, including CSP integrations (AWS, GCP, Azure)

Technical & Strategic Skills

  • People leadership: hiring, coaching, and performance management across product, design, and education
  • Product strategy: investment planning, ROI analysis, budgeting, and analytics
  • End-to-end product development: from discovery and design to docs and delivery
  • Analytics & Financial Modeling: SQL/Looker fluency, revenue forecasting, NRR/NDR, gross margin optimization, LTV:CAC, Rule of 40
  • Pricing & monetization: strategy informed by data science, customer research, and business modeling
  • Technical: Python, SQL, LLMs (GPT-5, Claude, Vertex AI), RAG, Vector Databases, Prompt Engineering

Let's Connect

Always up to explore the intersection of AI, finance, and infrastructure, or debate the perfect burger. Reach out on X or LinkedIn.

I advise early-stage companies on AI product strategy, 0-1 and 1-10 product development, and B2B software. I speak at conferences about building AI-native products, modern product management, and how finance and infrastructure are being rebuilt in the AI era.

About This Site

This website was built using Claude Code and Astro. The entire development process, from architecture decisions to implementation, was completed in under 4 hours using AI-native development practices.

Blog post hero images are AI-generated using Stable Diffusion to create custom artwork that complements each article's theme.