Booker DiMaio
IT modernization and software engineering
Artificial Intelligence Engineer
Two days on-site per week in Annapolis Junction; up to three days remote.
About the job
- Strong Python development skills, including experience writing production-quality, maintainable code.
- Hands-on experience building applications on top of existing large language models through application programming interfaces for commercial or self-hosted models.
- Experience designing multi-agent or multi-step artificial intelligence workflows, including prompt chaining, tool use, and agent orchestration through LangChain, LlamaIndex, or custom frameworks.
- Strong prompt engineering skills and experience evaluating and validating large language model outputs.
- Experience integrating artificial intelligence capabilities into existing software architectures, including RESTful APIs and microservices.
- Experience with the Amazon Web Services cloud computing platform.
- Lead the design and development of artificial intelligence-driven solutions from conception to deployment, including multi-agent workflows in which coordinated agents and prompts produce outputs supporting reporting and dissemination.
- Prototype, write production-quality code, and maintain deployed artificial intelligence capabilities.
- Integrate existing foundation models into existing software architectures through APIs and orchestration frameworks, selecting the appropriate model and approach for each task rather than building models from scratch.
- Design, test, and refine prompts and agent instructions to automate manual tasks reliably.
- Decompose complex mission workflows into discrete steps that an agent pipeline can execute.
- Develop testing, evaluation, and validation strategies for artificial intelligence-generated outputs, ensuring accuracy, consistency, and appropriate handling of edge cases before outputs reach analysts and reports.
- Serve as a key technical liaison with system engineers, software developers, and domain experts.
- Present and articulate recommended artificial intelligence approaches and discuss implementation tradeoffs and implications with technical and non-technical stakeholders.
- Stay current with large language model and agentic artificial intelligence developments, including new models, orchestration frameworks, and tooling, and identify practical opportunities to apply emerging capabilities to the system.
- Experience with retrieval-augmented generation pipelines and vector databases.
- Familiarity with large language model observability and evaluation tooling.
- Experience conducting exploratory data analysis on structured and unstructured datasets to prepare inputs for artificial intelligence workflows.
- Familiarity with machine learning operations and large language model operations practices for deploying and monitoring artificial intelligence capabilities at scale.
- Familiarity with domain knowledge concerning government agency reporting and dissemination policies.
About the company
Booker DiMaio helps government and national security clients modernize their technology with engineering and software transformation services. Its offerings span end-to-end tech services and a reseller-enabled portfolio from AWS, Microsoft Azure, FedRAMP Cloud Solutions, and SecuLore, combining cloud, analytics, DevSecOps, cybersecurity, and IT modernization delivered by cross-functional teams focused on mission needs and regulatory compliance. The company differentiates itself by assigning dedicated, project-specific teams with 90+ years of combined experience, a broad end-to-end solutions set, and a proven emphasis on user experience and compliance. Its goal is to help defense, intelligence, and civilian customers transform operations through practical, compliant, and effective software and infrastructure solutions.
Company Size
1-10
Company Stage
N/A
Total Funding
N/A
Headquarters
Sykesville, Maryland
Founded
2010
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Simplify's Take
What believers are saying
- IRS awarded Booker DiMaio a $2.18 million OCPO support task on September 11, 2026.
- FY2026 federal obligations reached $62,400 YTD, extending active government revenue.
- Open roles on September 12, 2026 signal execution capacity for new federal work.
What critics are saying
- Federal obligations total $4.04 million across four awards, leaving brutal customer concentration.
- One IRS task drives near-term growth; any recompete loss hits 2027 revenue.
- Loss of SeaPort NxG and 8(a) access would collapse the company’s pipeline.
What makes Booker DiMaio unique
- Booker DiMaio’s ServiceNow partnership pairs boutique federal IT with AI workflow automation.
- SeaPort NxG and 8(a) STARS III keep it inside hard-to-win government channels.
- Maria Booker and Sean Booker anchor founder-led selling and delivery.
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Benefits
Remote Work Options
Company News
Booker DiMaio has partnered with ServiceNow, currently the most effective resource for artificial intelligence (AI) and machine learning.