Jeffrey W. Small
Talkmap
San Francisco,CA
42
years of professional experience
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.
Work History
VP of Engineering
8 Years- Drove requirements and delivery of Nereus, a production multi-agent AI platform using supervisor pattern architecture, RAG with LanceDB, Agno framework, and Temporal orchestration.
- Defined requirements and led delivery of Nereus, a production multi-agent AI platform utilizing supervisor pattern architecture, RAG with LanceDB, Agno framework, and Temporal orchestration.
- Delivered Talkmap Connect, a complete suite of CCaaS platform integrations, in solo 9-day sprint using Claude Code to support critical company inflection point.
- Employed feature switches and A/B testing for gradual rollouts; maintained 99.9% SLA across 15 microservices; achieved SOC 2 Type II compliance.
- Transformed platform from structured discovery tool for data scientists into natural language interface for business users, enabling plain language questions to generate relevant attribute data and discoverable results.
- 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.
- Executed Talkmap Connect, a comprehensive suite of CCaaS platform integrations, in solo 9-day sprint using Claude Code, addressing a critical company inflection point.
Chief Technology Officer
1 Year- Led technology strategy that improved user engagement and retention metrics.
- Led technology strategy to enhance user engagement and retention initiatives.
- Collaborated with cross-functional teams to integrate innovative solutions, enhancing product functionality and user satisfaction.
- Oversaw software development lifecycle, ensuring projects met deadlines and aligned with strategic goals.
Senior Director of Engineering
2 Years 3 Months- 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 to develop educational technology solutions that enhanced user engagement and learning outcomes.
- Collaborated with cross-functional teams to define product specifications and requirements, ensuring alignment with strategic goals.
- Managed project timelines and resource allocation for engineering initiatives, delivering projects on time and within budget.
Director of Engineering - BIM 360
4 Years 9 Months- 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 organization-wide Google-grade testing discipline to enhance software quality.
- Led engineering teams to develop software solutions for design and manufacturing that improved project delivery and client satisfaction.
- Implemented best practices for software development and project management to streamline processes and align project outcomes with business objectives.
- Collaborated with cross-functional teams to align engineering goals with business objectives.
Senior Director of Technology
5 Years 1 Month- 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 that increased client engagement and transformed service delivery.
- Managed cross-functional teams to implement innovative technology solutions that addressed client needs.
- Oversaw integration of advanced systems that streamlined operations and enhanced service capabilities.
Senior Software Architect
1 Year 1 Month- Architected web and early mobile platforms, focusing on location-based and real-time systems. Guided teams to deliver traffic, fleet-tracking, and time-sensitive information services, securing major commercial partnerships.
- Developed software architectures for scalable, high-performance applications at Kivera, enhancing application reliability and user experience.
- Coordinated cross-functional teams to implement innovative technology solutions for clients, improving project delivery timelines and client satisfaction.
- Mentored junior developers on best practices and software development methodologies.
Director of Software Engineering
2 Years- 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 to design innovative procurement system solutions, enhancing user experience and operational efficiency.
- Managed project timelines and resource allocation across multiple software engineering initiatives, ensuring on-time delivery and alignment with business goals.
- Collaborated with cross-functional teams to define and refine software requirements and specifications, facilitating clear communication and alignment on project objectives.
Senior Software Architect
2 Years 9 Months- Designed scalable software architectures for complex enterprise applications, enhancing system performance and reliability.
- 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) and guiding platform design and delivery to meet aggressive launch timelines.
- Collaborated with cross-functional teams to define project requirements and specifications, aligning technical plans with business objectives.
- Led code reviews to ensure adherence to best practices and coding standards.
Chief Engineer / Senior Software Engineer - AutoCAD LT
5 Years- 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 deliver innovative software solutions, directly addressing needs of design professionals.
- Collaborated with cross-functional teams to enhance product features, resulting in improved functionality and user satisfaction.
- Drove strategic initiatives to enhance software performance, significantly elevating user experience.
General Manager & Chief Engineer - AutoSketch
9 Years- 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 streamline product development processes, improving collaboration and output quality.
- Implemented strategic initiatives that enhanced operational efficiency across departments, optimizing resource allocation.
- Oversaw financial planning and budget management for multiple projects, ensuring alignment with organizational goals.
Education
B.A. - Applied Mathematics
Skills
AI strategy
AI pipeline
AI integration
Evaluation and observability
Data infrastructure
AI product management
Cloud architecture
Backend architecture
Engineering leadership
Product and UX 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
08.2018 - CurrentRead More
Chief Technology Officer
Motimatic
08.2017 - 08.2018Read More
Senior Director of Engineering
Blackboard
04.2015 - 07.2017Read More
Director of Engineering - BIM 360
Autodesk
06.2010 - 03.2015Read More
Senior Director of Technology
PDI Ninth House
04.2005 - 05.2010Read More
Senior Software Architect
Kivera
02.2004 - 03.2005Read More
Director of Software Engineering
ProcurePoint, Inc.
02.2002 - 02.2004Read More
Senior Software Architect
NearSpace, Inc.
05.1999 - 02.2002Read More
Chief Engineer / Senior Software Engineer - AutoCAD LT
Autodesk
01.1994 - 01.1999Read More
General Manager & Chief Engineer - AutoSketch
Autodesk
01.1985 - 01.1994Read More
University of California
B.A. from Applied Mathematics
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