James R. McKernan
San Francisco, CA
Engineering leader with 20+ years of experience building high-performance software systems, resilient teams, and impactful companies. Proven track record of technical leadership in startups and early-stage ventures, with deep expertise in both venture-backed organizations and cutting-edge research environments.
EXPERIENCE
Stackpack — Principal Software Engineer
Sept 2024 - Sept 2025
Stackpack is an AI-powered vendor management platform that helps companies track, optimize, and save on software expenses and contracts.
Product Catalog & AI Enrichment
Owned the Product Catalog, the core engine for cross vendor insights at Stackpack. Architected and built a full stack UX for the customer success team that supercharged their onboarding processes and delivered near immediate insights to onboarding customers. The system included:
Multi-stage AI enrichment pipeline that automatically resolved vendor URLs even from ambiguous names and obscure vendors, scraped and semantically analyzed websites, and generated structured metadata (categories, descriptions, legal links), enabling instant categorization for new customer onboarding.
Human-in-the-loop enrichment review system using LLM function calling to generate suggestions that the customer success team could validate before applying across 1000s of catalog entries.
Full-featured internal web application for customer success team to manage catalog entries and review AI enrichment suggestions, including virtualized tables, multi-select bulk operations, and modal-based review workflows.
Technical Contributions
Implemented location dimension support for hotel chain customers with multi-site operations, extending data sync infrastructure and transaction data model to enable accurate spend tracking across locations, expanding Stackpack’s addressable customer base.
Extended spend insights capabilities through incremental feature additions, bug fixes, and customer-requested enhancements across trend analysis, alerts, and accounting workflows.
Adopted AI-assisted development practices to accelerate learning and delivery in TypeScript/React, enabling full-stack contributions to Product Catalog and customer-facing features
Built Upon: Golang, TypeScript / React, Vercel, gRPC, buf.build, GCP, ArangoDB, Weaviate, Redis, Claude, OpenAI, Cursor Agent (Anthropic).
Executed With: Shapeup, JIRA, Github, Notion.
Lead With: Grit, Ownership, Urgency & Empathy.
Pathpoint — VPE; SVP, Technology; Principal Software Engineer
Nov 2018 - Aug 2024
Pathpoint is changing how E&S commercial insurance is transacted by building technology that gives agents & underwriters superpowers. As VPE (and later SVP) I lead the technology function from inception to product-market fit and beyond:
- Early days included elbow-grease leadership, building the core web application from scratch with TypeScript, GraphQL, Golang, PostgreSQL, AWS w/ IaC, CI/CD w/ Github Actions.
- Hired the founding engineers, winning Pathpoint’s first customers, then grew it to several teams executing against multiple business objectives.
- The org built a service that delivered value to our customers, increasing MAUs many times over. Our investors noticed and we raised money in a time when the venture markets were retreating.
- Built the recruiting process that emphasized real-world evaluation and lightning-fast turnaround, winning top talent for both independent contributors and team leadership roles in the ultra-competitive Bay Area and remote.
- Retained top talent through a culture of inclusion, belonging, and support. We had near zero attrition through the toughest periods of the pandemic.
Entering 2022, the needs of the company shifted and I moved into an IC role as the company’s Principal Software Engineer. I hired my boss to focus on the organization while I focused on the technology, refining current systems, and enhancing or building new ones.
- Owned and executed the company’s Technology Roadmap, building consensus on which engineering-led projects would have the biggest impact on the org’s ability to deliver value faster while crafting innovative solutions to the company’s biggest technical problems.
- Upleveled the engineers and engineering leadership at the company through coaching, mentoring, and advising both ICs and EMs at all levels of the organization. Initiatives include crafting code styles, delivering tech talks and screen shares, lunch & learns and all hands demos, doing code / architecture reviews, one-on-one technical guidance sessions with more junior engineers, and leading & steering discussions at engineering leadership offsites.
- Continued to leverage my deep understanding of the architecture to deliver direct value day to day through both user-facing feature development and system level enhancements.
Emerald Cloud Lab — Director of Engineering
May 2014 - Sep 2018
Lead the ECL’s engineering team, reporting directly to the product focused Co-Founder/CEO. My team built the platform that included the services and infrastructure that formed the foundation of the cloud lab abstraction, as well as the frameworks that the scientific developers used to encode the lab experiments. Early work included writing much of the service layer code, but later shifted into a more leadership role with a focus on empowering the engineers to succeed.
HVF Labs (Affirm, Inc. // Glow, Inc.) — Advisor & Chief Architect
March 2012 - May 2014
Built infrastructure for HVFLab’s companies, the most notable being Affirm & Glow. Created reusable IaC components to stand up clouds quickly on AWS EC2. Technologies: AWS EC2, MySQL deployed in HA mode on EC2; coroutine python (gevent) for certain services.
Gave insight on pitches heard by HVF Investments (now Scifi.vc).
Previous Experience Available On Request
Jul 2001 - Jan 2012
Notable gigs include working at Slide, a pioneering social apps company that was later purchased by Google, working on infrastructure and services.
Details available on request, or visit my LinkedIn.
EDUCATION: Georgia Institute of Technology – B.S. (Honors), Computer Science
1997 – 2001