Dean Hiller
@deanhiller
Hands-on CTO and serial founder building AI-first B2B products and scaling teams.
United StatesWhat I'm looking for
I’m a serial founder and hands-on CTO who builds products from zero and scales them to exit. I’ve started and shipped multiple companies that were built and sold, and I’m currently co-founding an AI-first B2B SaaS platform with OpenAI and Claude integrations.
I’m equally comfortable writing production code and leading large engineering orgs. I’ve authored 4,026+ commits on my current venture, designed multi-tenant SaaS architecture, and built an AI-powered chat using OpenAI streaming plus the Claude Agent SDK—complete with tool calls for discovery, proposals, matching, and automated outreach.
On the leadership side, I’ve led 70 engineers, 7 managers, and 1 director as VP of Engineering, while driving technical strategy, culture, and delivery. From zero-to-product in 6 months at Orderly Health (including core product work used by TransUnion) to scaling systems at Twitter scale (150,000 notifications/sec delivery and a 10x ops-cost reduction via microservice rewrites), I bring deep expertise in AI/ML, distributed systems, cloud infrastructure, and full-stack execution.
Experience
Work history, roles, and key accomplishments
Co-Founder & CTO
TryTami
Aug 2024 - Present (1 year 9 months)
Co-founded an AI-first B2B training marketplace, delivering 4,026 commits and authoring 70.5% of the codebase. Architected OpenAI streaming + Claude Agent SDK chat, built a prompt microservice with dev/demo/prod versioning, and launched a multi-tenant SaaS with Stripe 3D Secure and role-based JWT auth.
VP of Engineering
Tray.com
Jul 2022 - Mar 2024 (1 year 8 months)
Led 70 engineers, 7 managers, and 1 director, setting technical strategy and delivery culture. Drove monolith-to-microservices and polyrepo-to-monorepo migrations, wrote the first three microservices, and raised hiring quality while standardizing 70% TDD coverage on new services.
First Engineer & CTO
Orderly Health
Jan 2019 - Jan 2022 (3 years)
Joined at 0 lines of code and built the core AI healthcare platform in 6 months, including 3 websites and a GCP-hosted API used by TransUnion. Managed an AI/ML team (3 engineers), scaled to 20 in 3 months while growing the company 4x, and built Elasticsearch plus scalable multi-product architecture.
Sr Developer & Search Lead
GNIP
Jan 2014 - Jan 2019 (5 years)
Contributed to GNIP’s growth leading to Twitter acquisition, working on firehose ingestion at ~30 servers with Kafka, Cassandra, and S3. Recreated business search in Scala with near-zero bug rate, delivered 150,000 notifications/sec to 500M+ devices, and rewrote 6 microservices to reduce ops cost by 10x.
Founder & CEO
Extreme Software LLC
Jan 2009 - Jan 2013 (4 years)
Founded and sold a software consultancy with an international Beijing office and distributed dev teams. Architected NREL DataBus, a Cassandra-based open-source platform handling 100,000+ events/sec, and delivered large-scale AWS and NoSQL modernization efforts including an 8TB Gemfire migration and Agile transformation.
Director of Architecture
Carrier Access
Jan 2005 - Jan 2008 (3 years)
Led architecture work in a telecom manufacturing environment, coordinating engineering direction across Shanghai-based operations. Drove architectural decision-making to support delivery of a $50M-scale product organization.
Lead Architect
Avaya/Lucent Technologies
Jan 1999 - Jan 2005 (6 years)
Served as a lead architect at Avaya/Lucent Technologies, contributing to a top-selling billion-dollar product. Built and evolved production software as part of a high-performance engineering organization from 1999–2005.
Education
Degrees, certifications, and relevant coursework
University of Michigan, Ann Arbor
Bachelor of Science in Engineering, Electrical Engineering
Grade: GPA: 3.59/4.0
Earned a BSE in Electrical Engineering at the University of Michigan, Ann Arbor with a GPA of 3.59/4.0.
University of Michigan, Ann Arbor
Bachelor of Science in Engineering, Computer Engineering
Grade: GPA: 3.59/4.0
Earned a BSE in Computer Engineering at the University of Michigan, Ann Arbor with a GPA of 3.59/4.0.
Beijing Normal University
Intensive Chinese Program, Chinese Language
Completed a 12-month intensive Chinese program at Beijing Normal University.
Availability
Location
United StatesAuthorized to work in
Website
ctoteachings.com/blogPortfolio
github.com/deanhillerJob categories
Skills
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