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Booker DiMaio

IT modernization and software engineering

AI Engineer

Full-TimeUpdated on 10/23/2026
No salary listed
Mid
Annapolis Junction, MD, USA
HybridHybrid schedule: up to 3 days/week remote and 2 days/week onsite in Annapolis Junction, MD.
Software EngineeringAI Application Engineering
No H1B Sponsorship
US Top Secret Clearance Required

About the job

Requirements
  • Strong Python development skills, including experience writing production-quality, maintainable code.
  • Hands-on experience building applications on top of existing large language models, such as through APIs for commercial or self-hosted models.
  • Experience designing multi-agent or multi-step AI workflows, including prompt chaining, tool use, and agent orchestration.
  • Strong prompt engineering skills and experience evaluating and validating large language model outputs.
  • Experience integrating AI capabilities into existing software architectures, including RESTful APIs and microservices.
  • Experience with the Amazon Web Services cloud computing platform.
Responsibilities
  • Lead the design and development of AI-driven solutions from conception to deployment, building multi-agent workflows in which coordinated agents and prompts produce outputs supporting reporting and dissemination.
  • Prototype, write production-quality code, and maintain deployed AI capabilities.
  • Integrate existing foundation models into existing software architectures via 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 reliably automate manual tasks, and decompose complex mission workflows into discrete steps an agent pipeline can execute.
  • Develop robust testing, evaluation, and validation strategies for AI-generated outputs, ensuring accuracy, consistency, and appropriate handling of edge cases before outputs reach analysts and reports.
  • Collaborate with system engineers, software developers, and domain experts as a technical liaison.
  • Present and articulate recommended AI approaches, discussing implementation tradeoffs and implications with technical and non-technical stakeholders.
  • Stay current with new large language models, agentic AI capabilities, orchestration frameworks, and tooling, and identify practical opportunities to apply emerging capabilities to the system.
Desired Qualifications
  • 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 AI workflows.
  • Familiarity with MLOps/LLMOps practices for deploying and monitoring AI capabilities at scale.
  • Familiarity with domain knowledge surrounding 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
Aug 4th, 2023
Real-World application examples

Booker DiMaio has partnered with ServiceNow, currently the most effective resource for artificial intelligence (AI) and machine learning.