Engagement Lead- Microsoft 365- Remote (Anywhere in the U.S.)

GuidePoint Security provides trusted cybersecurity expertise, solutions and services that help organizations make better decisions and minimize risk. By taking a three-tiered, holistic approach for evaluating security posture and ecosystems, GuidePoint enables some of the nation’s top organizations, such as Fortune 500 companies and U.S. government agencies, to identify threats, optimize resources and integrate best-fit solutions that mitigate risk.

GuidePoint Security is seeking an experienced Engagement Lead to oversee client relationships and drive successful delivery of cybersecurity consulting engagements. In this senior role, you will serve as the primary point of contact for enterprise clients, ensuring projects are executed with precision, transparency, and measurable impact. The Engagement Lead will balance strategic oversight with hands‑on management, guiding cross‑functional teams, aligning solutions to client objectives, and fostering long‑term partnerships. This position is ideal for a professional who thrives in a boutique consulting environment, where agility, personalized service, and trusted advisory are central to delivering differentiated value.

Role and Responsibilities

• Technical Oversight & Delivery: Proven ability to oversee technical delivery teams, ensuring quality, consistency, and alignment with client objectives.
• Client Management: Skilled at building and maintaining executive-level relationships, translating technical outcomes into business value.
• Escalation Management: Experienced in managing and resolving escalations, balancing client satisfaction with project scope and delivery realities.
• Account Executive Partnership: Ability to collaborate with Account Executives to identify growth opportunities, shape proposals, and support pre-sales activities.
• Leadership & Communication: Strong written and verbal communication skills with the ability to present to executives, lead workshops, and mentor technical teams.
• Architectural Leadership: Lead the design, implementation, and lifecycle management of practice services.
• Pre-Sales & Delivery Support: Contribute to the creation of Statements of Work (SOWs), Requests for Proposal (RFPs), and pre-sales solution design in partnership with Account Executives and delivery teams.
• Modern Workplace Strategy: Define and implement strategies for secure, efficient, and user-friendly adoption of services across enterprise environments.
• Security & Compliance: Establish and enforce enterprise-wide security and compliance frameworks, including data protection, insider risk management, and data loss prevention (DLP).
• Zero Trust Enablement: Apply Zero Trust principles across cloud and hybrid environments, leveraging identity, access, and threat protection controls such as MFA, conditional access, and continuous verification.
• Cross-Functional Collaboration: Partner with cybersecurity, compliance, and infrastructure teams to align cloud security architectures with regulatory, operational, and business requirements.
• Integration Expertise: Design and implement integrations between cloud platforms, SaaS applications, security tools, and endpoint management solutions to ensure cohesive protection.
• Automation & Optimization: Develop automation scripts, workflows, and orchestration processes to streamline administration, monitoring, and operational efficiency.
• Technical Mentorship: Provide leadership, mentoring, and oversight to engineers and delivery teams, fostering knowledge transfer and consistent execution across regions.
• Resiliency & Monitoring: Establish high-availability, disaster recovery, and monitoring strategies to ensure resilient and continuously protected cloud services.
• Governance & Adoption: Define governance models, lifecycle policies, and adoption frameworks to maximize business value and ensure sustainable security practices.
• Thought Leadership: Act as a subject matter expert for cloud security initiatives, migrations, and transformations, contributing to client roadmaps, executive briefings, and industry discussions.

Requirements

Technical Requirements

• 10+ years of IT experience with at least 6+ years focused on Microsoft 365 architecture, administration, and security.
• Proven track record leading enterprise-scale Microsoft 365 and Entra ID deployments, migrations, and modernization projects.
• Deep knowledge of Microsoft 365 services, including Exchange Online, Teams, SharePoint, and OneDrive.
• Strong understanding of Microsoft 365 security and compliance capabilities such as Purview, DLP, Insider Risk, eDiscovery, and Information Protection.
• Hands-on experience with automation and scripting (PowerShell, KQL, Graph API, Terraform, or equivalent).
• Solid understanding of cloud computing concepts, architectures, virtualization, containers, infrastructure security, data security, encryption, management plane, business continuity, and identity entitlement/access management.
• Familiarity with Microsoft Defender suite, Microsoft Sentinel, Intune, and Entra ID for identity integration and governance.
• Experience with lifecycle management of Microsoft 365 services, including provisioning, governance, and decommissioning.
• Minimum 2 years of experience with Microsoft 365 security suite capabilities such as Defender for Cloud Apps, Conditional Access, Microsoft XDR, Compliance Center, Insider Threat Management, DLP, MCAS, EOP, MFA, PIM, and PIP.
• Minimum 2 years of experience with Microsoft Azure security capabilities such as Defender for Cloud, Sentinel, WAF, APIM, Azure Policy, and related governance tools.

Certifications (preferred)

Microsoft Certified: Microsoft 365 Certified Enterprise Administrator Expert, Security Administrator Associate, or Azure Solutions Architect Expert.

We use Greenhouse Software as our applicant tracking system and Zoom Scheduler for HR screen request scheduling. At times, your email may block our communication with you. Please be sure to check your SPAM folder so that you don't miss updates on your application.

Why GuidePoint?

GuidePoint Security is a rapidly growing, profitable, privately-held value added reseller that focuses exclusively on Information Security. Since its inception in 2011, GuidePoint has grown to over 1000 employees, established strategic partnerships with leading security vendors, and serves as a trusted advisor to more than 4,200 customers.

Firmly-defined core values drive all aspects of the business, which have been paramount to the company’s success and establishment of an enjoyable workplace atmosphere. At GuidePoint, your colleagues are knowledgeable, skilled, and experienced and will seek to collaborate and provide mentorship and guidance at every opportunity.  

This is a unique and rare opportunity to grow your career along with one of the fastest growing companies in the nation.

Some added perks….

• Remote workforce primarily (U.S. based only, some travel may be required for certain positions, working on-site may be required for Federal positions)
• Group Medical Insurance options: Zero Deductible PPO Plan (GuidePoint pays 90% of the premium for employees and 70% for family plans (spouse/children/family) or High Deductible Health Plan with HSA (GuidePoint pays 100% of the employees premiums and 75% for family plans (spouse/children/family) and GPS will contribute in one lump sum: ($500 per EE annually / $1000 per family annually (includes spouse/children/family options)
• Group Dental Insurance: GuidePoint pays 100% of the premium for employees and 75% of family plans
• 12 corporate holidays and a Flexible Time Off (FTO) program
• Healthy mobile phone and home internet allowance
• Eligibility for retirement plan after 2 months at open enrollment
• Pet Benefit Option