Full-Time
Microsoft 365 / SharePoint Technical Support Specialist
Posted on 9/11/2026
Booker DiMaio
1-10 employees
IT modernization and software engineering
No salary listed
No H1B Sponsorship
Remote in USA
Remote
US Citizenship Required
 IT Operations (1) |
|---|
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- U.S. citizenship or Lawful Permanent Resident status with at least three consecutive years of U.S. residency from the date of legal entry as a lawful permanent resident.
- Eligibility to obtain and maintain IRS staff-like access and successfully complete the required Moderate Risk background investigation and security screening process.
- Successful completion of applicable IRS personnel-security requirements, including fingerprinting, security training, and related screening requirements.
- Demonstrated professional experience supporting U.S. Federal Government programs or federal government customers.
- Experience providing help desk, technical support, systems support, or platform monitoring.
- Strong troubleshooting and problem-solving skills.
- Ability to communicate effectively with both technical and non-technical users.
- Strong attention to detail and follow-through.
- Ability to document issues and work effectively within an established support process.
- Provide help desk and technical support for users of supported platforms and applications.
- Monitor platform and service performance and identify issues requiring attention.
- Troubleshoot user and platform problems and resolve issues within the scope of responsibility.
- Document incidents, requests, resolutions, and recurring issues.
- Escalate complex technical issues to appropriate technical subject-matter experts and development staff.
- Assist with user support, access issues, basic configuration, and operational tasks.
- Communicate clearly with users and technical team members regarding status and resolution.
- Support reliable, responsive day-to-day operation of the technical environment.
- Experience supporting Microsoft 365, SharePoint, or related enterprise platforms.
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
- A December 31, 2025 Army purchase order added CYBER TRAINING PLATFORM revenue.
- LinkedIn shows 1,143 followers, giving Booker DiMaio a visible recruiting and sales channel.
- ServiceNow's 2026 partner ecosystem keeps Booker DiMaio aligned with active enterprise AI demand.
What critics are saying
- Booker DiMaio remains tiny, with PitchBook showing 11 employees and fragile execution capacity.
- Federal obligations totaled $3.98 million across four awards, limiting revenue diversification.
- A contract lapse after August 2026 would hit cash flow and hiring immediately.
What makes Booker DiMaio unique
- Sean Booker runs a 11-50 person Maryland engineering firm founded in 2010.
- Booker DiMaio holds a ServiceNow partnership and markets enterprise AI workflow implementations.
- The firm won SeaPort NxG and GSA vehicles, supporting federal access.
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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.