Jeffrey W. Small
San Francisco Bay Area
Summary
Engineering executive leading teams in AI-powered product development. Spearheaded platform evolution into a natural language interface, enhancing user engagement with millions of conversations, while maintaining a 99.9% SLA across complex multi-agent systems. Drove significant revenue growth through innovative solutions and effective team scaling.
Overview
42
42
years of professional experience
Work History
VP of Engineering
Talkmap
09.2018 - Current
- Led requirements, architecture discussions, and delivery of multi-stage AI pipeline integrating classical ML (BERT-based intent classification, CRF entity extraction, dialogue act tagging) with LLM-based reasoning, processing millions of enterprise conversations while maintaining 99.9% SLA.
- Drove requirements and delivery of Nereus, a production multi-agent AI platform using supervisor pattern architecture, RAG with LanceDB, Agno framework, and Temporal orchestration.
- Employed feature switches and A/B testing for gradual rollouts; maintained 99.9% SLA across 15 microservices; achieved SOC 2 Type II compliance.
- Drove much of the product design and front-end architecture for Talkdiscovery, an enterprise conversational intelligence platform giving customers their first window into millions of customer conversations. Built on React 18 with real-time updates, interactive visualizations, and multi-dimensional filtering; designed UX from prototype to specification.
- Evolved the platform from a structured discovery tool for data scientists into a natural language interface for any business user, where questions in plain language automatically generated relevant attribute data and discoverable results.
- Developed comprehensive evaluation framework (gold standard datasets, regression harnesses, prompt review gates) alongside full observability layer (Arize Phoenix, Prometheus, Grafana, MLflow, Sentry) to enhance system reliability and performance.
- Delivered Talkmap Connect, a complete suite of CCaaS platform integrations, in solo 9-day sprint using Claude Code to support critical company inflection point.
Chief Technology Officer
Motimatic
09.2017 - 09.2018
- Led technology strategy to enhance user engagement and retention initiatives.
- Developed technology strategy for data-driven advertising platform, integrating behavioral science with analytics; stabilized analytics pipelines and resolved systemic data quality issues; implemented agile delivery practices.
- Collaborated with cross-functional teams to integrate innovative solutions into products.
- Oversaw software development lifecycle to ensure timely project delivery.
Senior Director of Engineering
Blackboard
05.2015 - 08.2017
- Scaled engineering organization from 2 to 15 Scrum teams (~100 engineers) across U.S. and APAC; modernized engineering practices for Learn LMS platform, enhancing support for universities and K-12 institutions globally.
- Led engineering teams in developing innovative educational technology solutions.
- Collaborated with cross-functional teams to define product specifications and requirements.
- Managed project timelines and resource allocation for multiple engineering initiatives.
Director of Engineering - BIM 360
Autodesk
07.2010 - 04.2015
- Directed go-to-market strategy for enterprise construction companies ($200M+ annual revenue), achieving $60M in first year; contributed to platform evolution into Autodesk Construction Cloud at $2.94B in revenue.
- Scaled engineering team to 100+ engineers through reassignment, acquihires, and direct hiring; established Agile methodology and implemented Google-grade testing discipline organization-wide.
- Led engineering teams to develop innovative software solutions for design and manufacturing.
- Implemented best practices for software development and project management across projects.
- Collaborated with cross-functional teams to align engineering goals with business objectives.
Senior Director of Technology
PDI Ninth House
05.2005 - 06.2010
- Directed technology strategy and engineering for an enterprise eLearning SaaS platform serving Fortune 500 clients with scalable online leadership development and talent management solutions.
- Led technology strategy to enhance client engagement and service delivery.
- Managed cross-functional teams to implement innovative technology solutions.
- Oversaw the integration of advanced systems for improved operational efficiency.
Senior Software Architect
Kivera
03.2004 - 04.2005
- Led architecture for web and early mobile platforms, focusing on location-based and real-time systems. Guided teams in delivering traffic, fleet-tracking, and time-sensitive information services, securing major commercial partnerships.
- Designed software architectures for scalable, high-performance applications at Kivera.
- Led cross-functional teams to implement innovative technology solutions for clients.
- Mentored junior developers on best practices and software development methodologies.
Director of Software Engineering
ProcurePoint, Inc.
03.2002 - 03.2004
- Led engineering efforts for Sequoia Capital-backed enterprise travel procurement SaaS platform serving Fortune 500 customers, creating robust architecture and reliable delivery of mission-critical application built on J2EE, Oracle, and BEA WebLogic.
- Led software development teams in designing innovative solutions for procurement systems.
- Managed project timelines and resource allocation for multiple software engineering initiatives.
- Collaborated with cross-functional teams to define software requirements and specifications.
Senior Software Architect
NearSpace, Inc.
06.1999 - 03.2002
- Designed scalable software architectures for complex enterprise applications.
- Led architecture design at Autodesk founder-backed startup delivering time- and location-aware information services for web and early mobile devices (Pocket PC, Palm OS). Guided platform design and delivery, collaborating with small, fast-moving teams to achieve aggressive launch timelines.
- Collaborated with cross-functional teams to define project requirements and specifications.
- Led code reviews to ensure adherence to best practices and coding standards.
Chief Engineer / Senior Software Engineer - AutoCAD LT
Autodesk
02.1994 - 02.1999
- Led engineering teams responsible for multiple releases of AutoCAD LT, growing revenue from $15M to $72M. Hired Autodesk's first Usability Engineer, establishing Usability Lab to gather real customer reactions to features during development. Conceived and developed AutoCAD Layouts feature, enhancing Paper Space functionality for improved user experience. Invented Multiple Output Device Association, contributing to innovation in software capabilities.
- Led engineering teams to develop innovative software solutions for design professionals.
- Collaborated with cross-functional teams to enhance product features and functionality.
- Drove strategic initiatives to improve software performance and user experience.
General Manager & Chief Engineer - AutoSketch
Autodesk
02.1985 - 02.1994
- Took over founder-written 2D CAD codebase as sole developer; expanded team to 17 with engineering, technical publications, and marketing/sales reporting directly, managing full P&L ownership. Developed AutoSketch into Autodesk's second-highest revenue product within 4 years.
- Directed cross-functional teams to enhance product development processes.
- Implemented strategic initiatives to improve operational efficiency across departments.
- Oversaw financial planning and budget management for multiple projects.
Education
B.A. - Applied Mathematics
University of California
Berkeley, CaliforniaSkills
- AI strategy development
- AI pipeline architecture
- AI integration strategies
- Evaluation and observability
- Data infrastructure
- Cloud architecture
- Frontend architecture
- Product and UX leadership
- Engineering leadership
Projects
PropIQ - Home & Property Intelligence Platform, 2025, Present, Built a complete home and property intelligence platform as an AI vibe-coding experiment.
Patents
Multiple Output Device Association, Autodesk, Inc., US 7,366,980, 04/29/08
Timeline
VP of Engineering
Talkmap
09.2018 - Current
Chief Technology Officer
Motimatic
09.2017 - 09.2018
Senior Director of Engineering
Blackboard
05.2015 - 08.2017
Director of Engineering - BIM 360
Autodesk
07.2010 - 04.2015
Senior Director of Technology
PDI Ninth House
05.2005 - 06.2010
Senior Software Architect
Kivera
03.2004 - 04.2005
Director of Software Engineering
ProcurePoint, Inc.
03.2002 - 03.2004
Senior Software Architect
NearSpace, Inc.
06.1999 - 03.2002
Chief Engineer / Senior Software Engineer - AutoCAD LT
Autodesk
02.1994 - 02.1999
General Manager & Chief Engineer - AutoSketch
Autodesk
02.1985 - 02.1994
B.A. - Applied Mathematics
University of California