Helper Connectwise Jobs in Silver Spring, MD (NOW HIRING)

JOB SUMMARY: The Senior Technical Lead serves as a senior technical authority and strategic advisor, owning the most complex client environments while driving consistency, quality, and innovation across service delivery. This role extends beyond individual client ownership to include mentoring Technical Leads, contributing to internal initiatives, and shaping best practices across the organization. The Senior Technical Lead ensures alignment between technology and business objectives while elevating both client outcomes and internal team capability, with deep expertise in Microsoft 365 and Azure environments.

ESSENTIAL FUNCTIONS:  

• Own and lead assigned client IT environments, with responsibility for the most complex, high-impact accounts, ensuring performance, scalability, and alignment with business objectives.  
• Serve as the primary technical authority for assigned clients, building trusted relationships with stakeholders and advising on complex technical and strategic decisions.  
• Act as a senior escalation point across client environments, resolving the most challenging infrastructure, cloud, and network issues.  
• Lead the design, architecture, and implementation of advanced solutions, particularly within Microsoft 365 and Azure environments.  
• Lead practical AI enablement efforts for clients, helping identify use cases, guide adoption, and distinguish between out-of-the-box AI capabilities and custom AI solution opportunities. 
• Provide technical leadership and guidance to Technical Leads, supporting solution design, troubleshooting, and overall service delivery quality.  
• Establish and promote technical standards and best practices across assigned clients, while influencing consistency across the broader client base.  
• Drive proactive strategy within assigned accounts, identifying risks, trends, and opportunities to improve performance and long-term outcomes.  
• Lead and contribute to cross-client or internal technical initiatives, supporting the evolution of services, tools, and delivery processes.  
• Partner with leadership to align technical execution with business priorities and drive continuous improvement across service delivery.  
• identify and address systemic issues across multiple environments, driving improvements beyond individual client scope. 
• Contributes to internal initiatives, such as process improvements, service development, or operational enhancements.  
• Build and maintain strong relationships with key client stakeholders, reinforcing confidence in both individual performance and the broader team's capabilities. 
• Leverage core operational platforms (e.g., ConnectWise, IT Glue, Kaseya) to drive effective service delivery, documentation quality, and reporting across assigned clients.

KNOWLEDGE, SKILLS & ABILITIES: 

• Advanced ability to design, architect, and support complex IT environments across cloud, on-premises, and hybrid infrastructures.  
• Deep, hands-on expertise in Microsoft 365 and Azure, including identity (Entra ID), endpoint management (Intune), collaboration platforms, security, and cloud infrastructure at scale.  
• Strong working knowledge of practical AI productivity tools and workflows, including prompt development, ChatGPT Projects, custom GPTs or Skills, Microsoft 365 Copilot capabilities, and AI-assisted productivity tools such as Claude for Excel. 
• Ability to guide clients from limited AI familiarity to practical adoption, including teaching effective prompting, identifying realistic business use cases, and helping teams apply AI safely and productively in day-to-day work. 
• Ability to assess when a client need can be addressed through existing AI tools versus when it should be escalated for custom AI solution design or development. 
• Strong understanding of Microsoft 365 AI capabilities, including Copilot-based research and productivity features, and how they can be applied in client environments. 
• Ability to independently own high-impact client environments, projects, and technical escalations with minimal oversight.  
• Ability to identify and address systemic issues across multiple environments, driving improvements beyond individual client scope.  
• Manages competing priorities across multiple client environments while contributing to broader organizational objectives.  
• Able to understand the core services offered by designDATA, with the ability to design and integrate solutions across multiple technology domains.  
• Ability to evaluate, standardize, and improve technical approaches across multiple client environments, driving consistency and best practices.  
• Strong leadership and communication skills, with the ability to influence technical direction and translate complex concepts into clear guidance for both technical and non-technical stakeholders.  
• Ability to mentor and develop other Technical Leads, elevating team capability and reinforcing high standards of execution.  
• Ability to manage competing priorities across multiple client environments while contributing to broader organizational initiatives.  
• Commitment to maintaining a high standard of service delivery, with a proactive, ownership-driven mindset and focus on continuous improvement.

QUALIFICATIONS: 

• 6+ years of progressive experience in IT infrastructure, systems administration, or managed services environments.  
• Deep proficiency across Microsoft cloud technologies, including identity (Entra ID), endpoint management (Intune), collaboration (Microsoft 365), and Azure infrastructure, is expected.  
• Proven experience leading complex Microsoft 365 and Azure environments at scale, including architecture, implementation, and long-term optimization across multiple clients or environments. 
• Exposure to Google Workspace and/or AWS environments, including administration and migrations.  
• Strong track record of operating in a client-facing role, building trusted relationships and advising stakeholders on complex technical and strategic decisions.  
• Experience with virtualization platforms (e.g., VMware) and Windows Server environments, including design, optimization, and troubleshooting.  
• Expert-level troubleshooting and problem-solving skills, with the ability to diagnose and resolve highly complex, multi-system issues and identify root causes across environments.  
• Strong understanding of networking concepts, including switching, routing, firewalls, and wireless infrastructure, with the ability to apply this knowledge in complex, real-world scenarios.  
• Experience leveraging and optimizing service delivery platforms (e.g., ConnectWise, IT Glue, Kaseya) to improve documentation quality, operational efficiency, and reporting.  
• Valid driver's license and reliable transportation for onsite client support, as needed.

Preferred:  

• Advanced Microsoft certifications (e.g., Azure Solutions Architect Expert, Microsoft 365 Enterprise Administrator Expert).  
• Broad experience or certifications in complementary technologies (e.g., networking, security, virtualization) are valued to support full-scope solution design.

WORKING ENVIRONMENT:  The majority of work is performed in a professional office setting with a wide variety of people with differing functions, personalities and abilities. Local travelwillberequiredtomeet with clients and participate in events.  Non-local travel may be required up to 10%.

REASONABLE ACCOMODATION: It is design DATA, Inc.'s business philosophy and practice to provide reasonable accommodations, according to applicable state and federal laws, to all qualified individuals with physical or mental disabilities.

PREFERENCE STATEMENT: design Data, Inc. grants preference to qualified Doyon Shareholders first, and second to qualified shareholders of other Alaska Native corporations that grant a similar preference in all phases of employment and training, which include, but are not limited to hiring, promotion, layoff, transfer, and training.

PAY TRANSPARENCY STATEMENT: design Data, Inc. will not discharge or in any other manner discriminate against employees or applicants because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant.  However, employees who have access to the compensation information of the other employees or applicants as a part of their essential job functions cannot disclose the pay of other employees or applicants to individuals who do not otherwise have access to compensation information, unless the disclosure is (a) in response to a formal complaint or charge, (b) in furtherance of an investigation, proceeding, hearing, or action, including an investigation conducted by the employer, or (c) consent with the contractor's legal duty to furnish information.

We are an equal opportunity employer and comply with all non-discrimination obligations, including the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA) and Section 503 of the Rehabilitation Act. 

We evaluate qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity or national origin, disability, veteran status, and other protected characteristics. The EEO is the Law, and the poster is available https://www.eeoc.gov/poster. For questions on the job posting contact (781) 312-8005.

If you need assistance or special accommodations during the application process, please contact the appropriate Human Resources Department at hr@doyontechgroup.com.