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Craig Barbieri

Craig Barbieri

Fractional CTO | AI & Digital Transformation Leader | AEC in Philadelphia, PA, USA

Craig Barbieri is a technology executive who leads AI and digital transformation in architecture, engineering, and construction. He has two decades of director-level technology leadership at firms from 500 to several thousand staff, twice operating as de facto CTO, building technology organizations from nothing and managing budgets up to $5M. He now runs Barbieri Technology Group, a fractional CTO practice covering AI strategy, governance, and adoption, and builds AI software products including TermsWatchdog. He holds an M.Arch and MLA from Penn.

About Craig

Philadelphia, PA, USA
Fractional CTO | AI & Digital Transformation Leader | AEC
Barbieri Technology Group

Function Experience More information about Function Experience

46% Software Development & Engineering
31% Operations
15% Strategy
8% Product

Industry Experience More information about Industry Experience

31% SaaS
31% Professional Services
23% Technology
15% Construction

Commitment Experience More information about Commitment Experience

38% Employee
31% Creator
23% Founder
8% Fractional Executive

Accomplishments

Built agentic business development CRM for AEC

Product Creator
ProspectPilot
March 2026 - April 2026

Summary

ProspectPilot is an agentic business development platform I built for my own practice. It crawls ENR Top 500 and Top 400 firm lists with Firecrawl, extracts leadership and tech-stack signals, applies AEC-tuned lead scoring, and drafts personalized Gmail outreach. Every draft passes a human review gate, and automation is toggled feature by feature. Built on Supabase, the Gmail API, and Inngest.

Developed project budget and staffing calculator web app

Product Creator
Feezible
May 2026 - Present

Summary

Feezible is a fee and staffing validation app I built for my small and midsize architecture firm clients. It converts project typology, construction type, floor count, finish level, funding program, and layout into staffing needs, hours per phase by role, projected sheet counts, total budget, and profitability analysis, including PHFA fee cap logic for affordable housing work. Output exports to PDF, Excel, and CSV. It answers the question firms usually answer on instinct: does this fee actually cover the work.

Architected and launched AI SaaS compliance product

Founder & Product Lead
TermsWatchdog
January 2025 - Present

Summary

TermsWatchdog analyzes Terms of Service, EULAs, and Privacy Policies and returns structured risk assessments. I am the sole founder, architect, builder, and operator: architecture through launch on Next.js 14, Supabase, the Claude API, Firecrawl, Stripe, and Upstash Redis, deployed on Vercel, plus DNS, transactional email, and payment integration. I designed the AI Transparency Card, a nutrition-label format scoring twelve compliance categories with a stoplight rating.

Enterprise digital transformation & post-merger integration

Director of Design Technology
Pennoni Associates Inc.
July 2013 - November 2014

Summary

I was the senior technology leader for design delivery systems at a 1,000-person engineering firm running 26 to 27 offices, reporting to the COO. I led the organization-wide move to BIM and VDC, directed technology integration for multiple acquisitions, and consolidated platforms, standards, licenses, and staff adoption across offices. I expanded and directed an eight-person team, creating new roles to support a distributed enterprise, and managed lifecycle for 189-plus applications.

Using AI technology to improve efficiency

Director of Digital Technology
EwingCole
July 2022 - July 2025

Summary

The imagery used in showcasing the design of buildings, is critical to Architects. They grab clients attention. They convey design ideas and concepts, and engage the client in the project. When I arrived a EwingCole, their visualization workflow was high effort, high cost and slow to produce results. Sometimes using their expensive render farm or even outsourced to 3rd party providers, and their results weren’t at the level I would expect for a large firm. I made it a priority to rethink this model. I introduced a number of Gen AI tools and workflows to deliver best of class visualization.

Built prompt engineering assistant application

Product Creator
IntentIQ
June 2026 - Present

Summary

IntentIQ prompt strategy is a prompt engineering assistant I designed and built for my clients. It analyzes the intent behind a prompt, surfaces hidden assumptions, flags anti-sycophancy risks, then constructs an optimized prompt with an assessment report. Users configure it by analysis perspective, output type, thinking mode, and rigor level. The goal was to make AI output quality repeatable across a team instead of dependent on whoever happens to be typing.

AI SaaS product from idea to launch and beyond

Founder and Chief Architect
TermsWatchdog
January 2026 - April 2026

Summary

Founded TermsWatchdog. I took an AI SaaS product from idea to launch: architecture, full-stack build, brand, GTM, and a B2B trust certification program. The "AI Transparency Card" framework is genuinely novel and an important tool for firms of all sizes. Most fractional CTOs advise on products like this; I built one.

Directed global practice technology and post-merger tech

Director of Practice Technology
Jacobs Engineering / KlingStubbins
March 2007 - June 2013

Summary

I directed design technology across six international offices, reporting strategically to the CEO and working tactically with the COO, and created and led a 12-person team. I ran the implementation of BIM and VDC as core delivery methods, standardizing digital workflows across architecture, engineering, and interiors globally. After the Jacobs acquisition I played a key role in harmonizing systems, standards, and infrastructure between the legacy firms, and I led enterprise VDI adoption well ahead of industry norms.

Led enterprise digital technology and de facto CTO role

Director of Digital Technology
EwingCole
July 2022 - July 2025

Summary

I led technology strategy for a 500-plus person national architecture and engineering firm across seven offices, operating as the senior-most technology voice and partnering directly with C-suite leadership. I built two organizations from nothing, Design Technology and Digital Media, and owned a $5M annual technology portfolio. The work spanned the firm's first AI policy and AI deployments, cloud migration to Autodesk Construction Cloud and Egnyte, a CMMC Level 1 secure enclave on AWS, and a portfolio of 130-plus automation tools.

Built multi-tenant social media scheduling platform

Product Creator
PostPilot
April 2026 - Present

Summary

PostPilot is a multi-tenant social scheduling and publishing platform I built as an alternative to Hootsuite and Buffer, covering Bluesky, Twitter/X, LinkedIn, Facebook, and Instagram. Built solo on Next.js, Supabase, and Vercel. It started as a way to run my own three-account brand strategy without paying enterprise pricing for features I did not need.

Spearheaded firm-wide digital transformation and cloud

Director of Design Technology
FCA Inc.
June 2015 - July 2020

Summary

I owned firm-wide digital transformation strategy and platform modernization for a national architecture and planning firm, covering the enterprise systems behind design, collaboration, and client delivery across every office. I built a transformation roadmap that tied business priorities to measurable improvements in design, project management, and delivery workflows, led the move to cloud platforms including Autodesk Construction Cloud, and managed enterprise licensing and multimillion-dollar vendor relationships.

Provided fractional CTO leadership and AI governance

Founder & Fractional Chief Technology Officer
Barbieri Technology Group LLC
January 2025 - Present

Summary

I run an independent fractional CTO practice for architecture and engineering firms of roughly 30 to 500 staff across the Northeast and Canada, most of which have no full-time technology leader. The work covers AI policy and governance, digital practice and AI-readiness assessments, BIM governance, platform selection, and executive AI enablement. I engage directly with CEOs, COOs, principals, and firm owners, and I translate assessments into prioritized roadmaps with measurable outcomes.

Modernized enterprise cloud and field technology

Director of Technology & Innovation
Norwood Construction
July 2020 - July 2022

Summary

I directed enterprise technology across preconstruction, operations, and field coordination for a growing construction firm, covering headquarters and active project sites. I led a cloud-first platform modernization, introducing a Common Data Environment and project information management through Autodesk Construction Cloud, Procore, StructionSite, and Microsoft 365. I also put augmented reality and LIDAR reality capture on active sites, designed hybrid IT and OT infrastructure, and set up a vendor governance framework.

References

Craig hasn't added any references yet

Experience

ProspectPilot

Software Engineering

ProspectPilot is an agentic business development platform I built for my own practice. It crawls ENR Top 500 and Top 400 firm lists with Firecrawl, extracts leadership and tech-stack signals, applies AEC-tuned lead scoring, and drafts personalized Gmail outreach. Every draft passes a human review gate, and automation is toggled feature by feature. Built on Supabase, the Gmail API, and Inngest.

Feezible

Web Development

Feezible is a fee and staffing validation app I built for my small and midsize architecture firm clients. It converts project typology, construction type, floor count, finish level, funding program, and layout into staffing needs, hours per phase by role, projected sheet counts, total budget, and profitability analysis, including PHFA fee cap logic for affordable housing work. Output exports to PDF, Excel, and CSV. It answers the question firms usually answer on instinct: does this fee actually cover the work.

TermsWatchdog

Product Management

TermsWatchdog analyzes Terms of Service, EULAs, and Privacy Policies and returns structured risk assessments. I am the sole founder, architect, builder, and operator: architecture through launch on Next.js 14, Supabase, the Claude API, Firecrawl, Stripe, and Upstash Redis, deployed on Vercel, plus DNS, transactional email, and payment integration. I designed the AI Transparency Card, a nutrition-label format scoring twelve compliance categories with a stoplight rating.

Pennoni Associates Inc.

IT Operations

I was the senior technology leader for design delivery systems at a 1,000-person engineering firm running 26 to 27 offices, reporting to the COO. I led the organization-wide move to BIM and VDC, directed technology integration for multiple acquisitions, and consolidated platforms, standards, licenses, and staff adoption across offices. I expanded and directed an eight-person team, creating new roles to support a distributed enterprise, and managed lifecycle for 189-plus applications.

EwingCole

Corporate Strategy

The imagery used in showcasing the design of buildings, is critical to Architects. They grab clients attention. They convey design ideas and concepts, and engage the client in the project. When I arrived a EwingCole, their visualization workflow was high effort, high cost and slow to produce results. Sometimes using their expensive render farm or even outsourced to 3rd party providers, and their results weren’t at the level I would expect for a large firm. I made it a priority to rethink this model. I introduced a number of Gen AI tools and workflows to deliver best of class visualization.

IntentIQ

AI/ML Engineering

IntentIQ prompt strategy is a prompt engineering assistant I designed and built for my clients. It analyzes the intent behind a prompt, surfaces hidden assumptions, flags anti-sycophancy risks, then constructs an optimized prompt with an assessment report. Users configure it by analysis perspective, output type, thinking mode, and rigor level. The goal was to make AI output quality repeatable across a team instead of dependent on whoever happens to be typing.

TermsWatchdog

Business Operations

Founded TermsWatchdog. I took an AI SaaS product from idea to launch: architecture, full-stack build, brand, GTM, and a B2B trust certification program. The "AI Transparency Card" framework is genuinely novel and an important tool for firms of all sizes. Most fractional CTOs advise on products like this; I built one.

Jacobs Engineering / KlingStubbins

Global Operations

I directed design technology across six international offices, reporting strategically to the CEO and working tactically with the COO, and created and led a 12-person team. I ran the implementation of BIM and VDC as core delivery methods, standardizing digital workflows across architecture, engineering, and interiors globally. After the Jacobs acquisition I played a key role in harmonizing systems, standards, and infrastructure between the legacy firms, and I led enterprise VDI adoption well ahead of industry norms.

EwingCole

Enterprise Systems Development

I led technology strategy for a 500-plus person national architecture and engineering firm across seven offices, operating as the senior-most technology voice and partnering directly with C-suite leadership. I built two organizations from nothing, Design Technology and Digital Media, and owned a $5M annual technology portfolio. The work spanned the firm's first AI policy and AI deployments, cloud migration to Autodesk Construction Cloud and Egnyte, a CMMC Level 1 secure enclave on AWS, and a portfolio of 130-plus automation tools.

PostPilot

Full Stack Development

PostPilot is a multi-tenant social scheduling and publishing platform I built as an alternative to Hootsuite and Buffer, covering Bluesky, Twitter/X, LinkedIn, Facebook, and Instagram. Built solo on Next.js, Supabase, and Vercel. It started as a way to run my own three-account brand strategy without paying enterprise pricing for features I did not need.

FCA Inc.

Enterprise Systems Development

I owned firm-wide digital transformation strategy and platform modernization for a national architecture and planning firm, covering the enterprise systems behind design, collaboration, and client delivery across every office. I built a transformation roadmap that tied business priorities to measurable improvements in design, project management, and delivery workflows, led the move to cloud platforms including Autodesk Construction Cloud, and managed enterprise licensing and multimillion-dollar vendor relationships.

Barbieri Technology Group LLC

Digital Transformation Strategy

I run an independent fractional CTO practice for architecture and engineering firms of roughly 30 to 500 staff across the Northeast and Canada, most of which have no full-time technology leader. The work covers AI policy and governance, digital practice and AI-readiness assessments, BIM governance, platform selection, and executive AI enablement. I engage directly with CEOs, COOs, principals, and firm owners, and I translate assessments into prioritized roadmaps with measurable outcomes.

Norwood Construction

IT Operations

I directed enterprise technology across preconstruction, operations, and field coordination for a growing construction firm, covering headquarters and active project sites. I led a cloud-first platform modernization, introducing a Common Data Environment and project information management through Autodesk Construction Cloud, Procore, StructionSite, and Microsoft 365. I also put augmented reality and LIDAR reality capture on active sites, designed hybrid IT and OT infrastructure, and set up a vendor governance framework.

Skills

Agentic AI AI Product Development Workflow Automation Business Development Full-Stack Development Product Strategy Web Application Development AEC Domain Expertise SaaS Architecture AI Governance Go-to-Market Digital Transformation BIM Governance Post-Merger Integration Team Building IT Portfolio Management Innovation AI Artificial intelligence Prompt Engineering AI Strategy Product Design Entrepreneurship Technology Leadership Global Team Leadership Digital Standards Technology Strategy AI Adoption Vendor Negotiation SaaS Product Development Cloud Migration Change Management Design Technology Fractional CTO Executive Advisory Reality Capture IT Strategy Vendor Management Construction Technology