Senior Technical Strategic Advisor

Senior Technical Strategic Advisor (Level 3)

Company: Advantage Technology, LLC
Department: Technical Strategic Advisory / Managed Services
Location: Frederick, Maryland
Job Type: Full-Time
Work Arrangement: Frederick Office / Customer-Facing Field Role
Salary Range: $100,000–$150,000 annually, based on qualifications and experience

Job Summary

Advantage Technology is seeking an experienced Senior Technical Strategic Advisor (TSA Level 3) to join our growing Frederick, Maryland team.

This position is ideal for an experienced IT Manager, IT Director, Technology Consultant, or senior IT professional who has spent years overseeing technology environments, supporting business operations, managing technology priorities, and working with technical teams.

We are looking for someone with broad technology knowledge, strong business judgment, excellent communication skills, and the ability to develop trusted relationships with business executives and IT leadership.

As a Senior Technical Strategic Advisor, you will serve as the primary strategic technology advisor for assigned managed services and enterprise customers. You will help customers understand their technology environments, plan future investments, identify risks, and ensure Advantage Technology delivers the services and solutions it has committed to provide.

You do not need to be a subject matter expert in every technology discipline. Advantage has specialized engineering, networking, cybersecurity, cloud, and other technical teams to provide deep technical expertise.

Your responsibility is to understand the customer's overall technology environment, recognize risks and opportunities, ask the right questions, bring in the appropriate specialists, and help customers make informed technology decisions.

This is a strategic, customer-facing technology leadership position—not a traditional sales, help desk, or hands-on engineering role.

Key Responsibilities

Strategic Customer Relationships

• Serve as the primary post-sale strategic technology advisor for assigned managed services and enterprise customers.

• Develop trusted relationships with business owners, CEOs, CFOs, IT Managers, IT Directors, and other executive stakeholders.

• Understand each customer's business operations, technology environment, objectives, challenges, and long-term priorities.

• Conduct regular customer technology reviews, including formal quarterly strategic business reviews.

• Help customers understand their technology needs and make informed decisions about technology investments.

• Coordinate with Advantage's Business Development team to maintain continuity of important customer relationships.

Technology Strategy and Planning

• Develop and maintain technology roadmaps aligned with each customer's business goals.

• Assist customers with annual technology budgets, infrastructure lifecycle planning, and multi-year investment priorities.

• Review customer technology environments involving networks, servers, Microsoft 365, cloud services, cybersecurity, backup systems, and business applications.

• Identify areas where technology improvements could enhance reliability, security, efficiency, productivity, or business operations.

• Recognize technology risks and involve Advantage's subject matter experts for detailed technical assessments and recommendations.

• Work with specialists in cybersecurity, networking, cloud, infrastructure, and other technical disciplines to develop appropriate solutions.

• Help customers evaluate emerging technologies, including AI and automation, based on business needs and practical value.

• Translate technical recommendations into understandable business priorities, budgets, and action plans.

Customer Advocacy and Service Delivery

• Understand the technology services each customer has purchased and the commitments Advantage has made.

• Verify that contracted services are being delivered appropriately and providing the expected value.

• Monitor overall customer satisfaction, technology health, open concerns, and service delivery performance.

• Identify potential service deficiencies, technology risks, or customer concerns before they become larger problems.

• Coordinate with Advantage's service delivery, engineering, cybersecurity, and project teams to address customer needs.

• Follow through on commitments and ensure responsible teams are accountable for resolving identified issues.

• Serve as a trusted advocate for customers within Advantage Technology.

Customer Retention and Growth

• Develop lasting customer relationships built on trust, communication, and consistent follow-through.

• Support customer retention, contract renewals, and long-term strategic account development.

• Identify opportunities to improve customer technology environments and achieve business objectives.

• Collaborate with Sales and Solutions Engineering to develop appropriate technology recommendations and expansion opportunities.

• Help customers understand the business benefits, costs, and priorities associated with proposed technology investments.

• Mentor and assist less experienced Technical Strategic Advisors when appropriate.

Required Qualifications

• 10 or more years of progressive experience in information technology, IT management, technology consulting, managed services, or related technical leadership roles.

• Broad working knowledge of business technology environments, including networking, servers, cloud services, Microsoft technologies, cybersecurity, and IT infrastructure.

• Experience managing or overseeing technology operations, systems, vendors, projects, or technical teams.

• Demonstrated ability to communicate effectively with business owners, executives, IT professionals, and technical specialists.

• Experience participating in technology planning, budgeting, infrastructure improvements, or business technology decisions.

• Ability to evaluate technology environments, recognize business risks, and identify where specialized technical expertise is needed.

• Strong customer relationship management, communication, organizational, and problem-solving skills.

• Ability to coordinate technical resources and follow through on customer commitments.

• Strong business judgment, accountability, and ability to manage multiple customer relationships.

• Willingness to travel to customer locations throughout the Maryland, Washington, DC, and Northern Virginia region as required.

Preferred Qualifications

• Previous experience as an IT Manager, IT Director, Technology Consultant, Senior IT Generalist, or Managed Services Technical Account Manager.

• Experience working with a Managed Service Provider (MSP) or Managed Security Service Provider (MSSP).

• Experience managing an internal IT department or overseeing technology operations for a business.

• Familiarity with Microsoft 365, Azure, cloud infrastructure, networking, cybersecurity, and business continuity.

• Experience developing technology roadmaps, annual IT budgets, or infrastructure lifecycle plans.

• Experience working with external technology vendors, consultants, and specialized engineering teams.

• Familiarity with ConnectWise or similar managed services management platforms.

• Industry certifications or technical training are beneficial but not required.

What We're Looking For

The ideal candidate is an experienced IT professional who understands the big picture.

You may have spent much of your career as an IT Manager, IT Director, senior IT generalist, or technology consultant responsible for keeping a company's technology operating effectively.

You understand the major components of a business technology environment, how they work together, and how technology decisions affect company operations.

You know how to work with specialized engineers and technical experts without needing to personally perform every engineering task.

You enjoy meeting with business leaders, understanding their challenges, developing technology plans, coordinating resources, and helping organizations make better technology decisions.

We value broad technical understanding, business judgment, strong relationships, personal accountability, and follow-through.

About Advantage Technology

Founded in 2002, Advantage Technology is a growing technology services company headquartered in Charleston, West Virginia, with additional offices in Bridgeport, WV, and Frederick, MD.

We provide comprehensive technology solutions including managed IT services, cybersecurity, cloud infrastructure, networking, Microsoft technologies, telecommunications, physical security, and technology consulting.

Our mission is to help customers operate more reliably, efficiently, and securely through innovative technology solutions and trusted customer relationships.

Why Join Advantage Technology?

• Join an established and growing technology services company expanding throughout the DMV region.

• Build meaningful relationships with business owners and executive leadership.

• Work alongside experienced subject matter experts in cybersecurity, networking, cloud, infrastructure, and other technologies.

• Help customers develop long-term technology plans and make better business decisions.

• Enjoy a strategic, relationship-focused position without being responsible for day-to-day help desk or engineering work.

• Make a measurable impact on customer satisfaction, retention, and long-term growth.

• Opportunities for continued professional development and career advancement.

If you are an experienced IT professional who enjoys helping businesses plan, manage, and improve their technology environments, we encourage you to apply.

Advantage Technology is an Equal Opportunity Employer.