Fractional CTO & Software Architect — Atlanta, GA
Hi, I'm Jamal. I bring Principal‑level judgment to production AI systems.
Fractional CTO and Principal engineering for teams shipping AI and the platforms it runs on: architecture, technical strategy, and hands‑on delivery from prototype to production.
Over a decade across Apple, Box, Sony, and Consumer Reports, plus startups backed by Sequoia, Founders Fund, a16z, and Techstars. Products in use across most of the Fortune 100; led ScriptSense through its acquisition in 2025.
Every engagement ends the same way: a system that holds up, a team that ships faster, and technical decisions someone senior finally owns.
The gap
The first version shipped. What comes next is a different problem.
Every team gets to a first version. What stalls them is everything after:
- The AI feature that demoed well drifts in production, costs climb, and one prompt change quietly breaks two others.
- The platform that got you here can’t carry the next stage. Releases get slower, incidents get louder, and every change feels risky.
- The team is shipping, but no one owns the architecture, so every technical decision turns into a debate.
- Nobody senior enough is in the room for the calls that compound: build or buy, hire or contract, rewrite or harden.
That isn’t a model problem or a headcount problem. It’s an ownership problem: someone senior deciding what to build, what to measure, what to harden, and what to stop, while the team keeps shipping. Sometimes that’s AI. Sometimes it’s the platform underneath it. Usually it’s both. That’s the gap.
How I help
Find out what’s actually broken, then ship past it.
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01
Find where the system is really failing
Not “the model is bad” or “we need more engineers.” Whether it’s the architecture, the data, the evaluation gap, the platform, or the org, and which one to fix first.
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02
Sequence the next 90 days from prototype to production
Clear technical decisions: what ships, what gets hardened, what stops. Architecture direction and hands‑on code, not a slide deck.
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03
Leave a system your team can run without me
Evaluation, observability, engineering standards, and a stronger team in place, so reliability compounds after the engagement ends.
How we work together
Two ways in. One kind of team.
A fixed‑scope Architecture & Production Readiness Review, or ongoing Fractional CTO / Principal Engineer leadership alongside your team.
Built for funded teams shipping AI, or scaling the platform it runs on, without a senior technical owner — from first product in production through enterprise modernization.
For a look at the work
ScriptSense - An agentic AI platform that transformed entertainment IP into structured, searchable intelligence.
Led architecture and engineering as ScriptSense evolved from a script-analysis tool into a production AI platform for entertainment intelligence — acquired by Cinelytic in 2025.
Related work: production reliability at Box, evaluation systems at Elly.ai, agentic workflows for Consumer Reports, and sustainability‑focused AI pipelines for Circular.
Latest writing
Why Every AI Incident Becomes an Engineering Incident
Sales ops owns the workflow. Engineering owns the incident. The gap between those two sentences is more expensive than the hours it burns. A discount-approval agent sits inside…
The book
I wrote the book on this.
The Decision Gap: why you can trace every step and still not know why. Every team running AI in production can replay what their system did. Almost none can explain why. This book is about the gap between those two facts, and what it costs.
Testimonials
A few words from people I've worked with.
“They're a highly skilled developer with a strong work ethic.”
ScriptSense: a custom AI platform for Cinelytic, built and maintained over 19 months. Verified on Clutch at 5.0 across quality, schedule, and cost.
Built and maintained our platform. Well organized, delivers the development roadmap on time. They’re a highly skilled developer with a strong work ethic.
Tobias Queisser
CEO · Cinelytic
“When put under pressure, he kept his focus and delivered on time.”
Early-career engineering at Apple, growing and delivering under pressure.
Enthusiastic, attentive, calm and poised to perform, are the features define Jamal. Since the day he joined, I’ve seen him learn, grow and collaborate for the success of the team. Wish him success in all his future endeavors.
Royston DSouza
Engineering Leader · Apple
“The solution Jamal developed not only enhanced our current transcription performance but also positioned Elly for long-term success.”
AI transcription at scale: accuracy, speaker differentiation, and real-time processing for enterprise clients.
I had the pleasure of working with Jamal Jackson when he joined the Elly.ai team to enhance our transcription capabilities. From day one, Jamal integrated seamlessly into the team, quickly grasping our workflows and collaborating effectively with both technical and non-technical stakeholders. His ability to understand the core challenges of AI-powered transcription, including accuracy, speaker differentiation, and real-time processing, was evident in his thoughtful approach to problem-solving.
Jamal had a noticeable impact in helping Elly’s ability to scale with large conversations and complex mapping of transcription insights to custom template write ups based on end user requests.
His work laid the groundwork for greater scalability, allowing us to serve a broader market and support larger enterprise clients with more complex needs.
I highly recommend Jamal for any AI engineering role—especially in environments that require deep technical expertise, a keen understanding of user needs, and a vision for scalable growth.
Kristen Habacht
CEO · Elly.ai
“The role Jamal plays in the success of our organization and in our ability to deliver consistently cannot be overstated.”
Enterprise engineering at Box: the hardest frontend work, delivered ahead of time.
He is a deeply technical frontend expert, who takes on the most challenging pieces of work with great delight and passion. Once Jamal is on it, you know it will get done ahead of time and with excellent quality. He always finds what to improve and addresses it proactively. Jamal is a true leader by example.
Eddie Flaisler
Head of Enterprise Engineering · Box
“At Circular, he helped us set a mature direction on how we integrate LLMs into our product.”
LLM integration direction for the product, from a CTO's seat.
Jamal is a true all-round engineer. In a team, he is thoughtful, respectful of others and always gives valuable perspectives.
James Nicolson
CTO · Circular
“Jamal has a deep and diverse technical skillset capable of finding a solution to any issue I brought to him.”
First MVP for a UX-focused founder-led project.
Jamal is a pleasure to work with and a great partner. He is friendly, calm, attentive, responsive, and reliable. His confidence and experience were crucial contributions to my nascent UX-focused project as we built out a first MVP together. He would be a valuable member to a team of any size.
Augustus Christensen
Founder · ShareScoops
“Jamal was able to overhaul our entire processing framework to improve accuracy and efficiency within the product.”
Six months turning large, unstructured data into detailed outputs, unlocking new products.
Jamal has been an absolute pleasure to work with over the past 6 months. The core functionality of our product is reliant on taking large, unstructured data and transforming it into consumable, but deeply detailed, outputs. Jamal’s experience over the past few years has placed him in the upper echelon of engineers that are able to accomplish this.
Taking the problem head on, As a result, we have had the opportunity to introduce new products that have grown our overall footprint and value creation for our customers. As we look forward, Jamal’s work will continue to have an outsized impact!
Nic Mahaney
Founder · Elly
“Jamal delivers high-quality work while also being a great mentor to other engineers.”
Team mentorship, enterprise-scale readiness, and leading a six-plus engineer team through a refactor.
Scope of work covered three areas for us: team mentorship, developing our engineers and raising the bar on how the group worked; refining the product for enterprise scale, getting it ready to handle larger customers and real load; and leading a team of six-plus engineers to scale the product and refactor key parts of the codebase.
FAI Agency successfully delivered a scalable product while improving developer experience through AI skills, maintaining high standards for quality and security, and consistently delivering on time.
Tim Maliyil
CEO · PerkyPet
“He was able to take complex requirements and translate them into effective, reliable solutions.”
Complex requirements delivered with off-shore engineering teams, through a generous handoff.
I had the great pleasure of working with Jamal. From the very beginning, collaboration was seamless. I felt it was easy for us to align on goals and discuss openly about how we can make the project a success. Jamal was very flexible with our timelines and budget too, which is difficult to find for someone as experienced as he is.
His technical aptitude was evident from day 1. He was able to take complex requirements and translate them into effective, reliable solutions, especially when working with off-shore engineering teams. Even as project needs evolved, he handled change with flexibility and professionalism, always finding a path forward.
I was particularly impressed by him going the extra mile during the handoff process, as Jamal was super generous with his time and experience. It was clear that he cared about the outcomes of the project and wanted it to be successful.
I look forward to the next time we’re able to work with Jamal again.
Zhi Ming Gan
Co-Founder · Bodhium Labs
About
I’m Jamal, a fractional CTO and software architect based in Atlanta. I’ve spent over a decade building production systems — at Apple, Box, Sony, and Consumer Reports, and inside startups backed by Sequoia, Founders Fund, a16z, and Techstars.
Most recently I led architecture and engineering as ScriptSense grew from a script‑analysis tool into a leading AI-assisted IP management platform, acquired by Cinelytic in 2025.
FAI exists because I kept seeing the same pattern: sharp teams with a working prototype and no one senior enough to get it to production without breaking it.
When you work with FAI, you work with me. Not a team I hand you off to.