Principal Engineer & Virtual CIO

Job Description

Job Description

About Us

Founded in 1998, Advantage Microsystems provides complete, outsourced IT departments for nonprofits and businesses with 100 to 1,000 employees across the Bay Area. Our clients are mission-driven organizations — nonprofits, behavioral health providers, and professional services firms — who rely on us as their full technology team. Our approach is built on three pillars: Service, Security, and Strategy. We don't just keep the lights on; we help clients build toward something. We're a well-established firm with strong team dynamics, a culture of mutual respect, and zero tolerance for micromanagement. We hire responsible people and trust them to do their jobs.

 

Advantage Microsystems is seeking an exceptional engineer to serve as a technical anchor for our clients and a collaborative force on our team. This is a role for someone who has already operated as an L3 or lead engineer — and who combines deep technical expertise with the presence and communication skills to serve as a fractional IT leader for our clients. You'll own complex architecture and escalations, but you'll also build IT roadmaps, develop technology budgets, and lead quarterly business reviews with executive stakeholders. If you can hold your own in a server room and a boardroom, we'd love to talk.

 

We promote to this level from within whenever possible — this is a rare external search driven by our current growth.

 

Why Advantage Microsystems?

1. Tenure – Our average employee tenure is 9.5 years. We think that speaks for itself.
2. Compensation – Our people are well compensated with pay and benefits, because employee retention is extremely important to us.
3. Ownership and Impact – You'll have real ownership over client outcomes, architecture decisions, and technical standards. You'll be working within a strong team and well-developed systems, with experienced colleagues and a CIO who want your expertise and judgment in the mix.
4. Culture – Our team is great. We have each other's backs, we have fun with our work, and our clients love us. We're all learning and growing together, so input and suggestions from our engineering staff directly shape how we operate.
5. Lifestyle – We were a work-from-home company before COVID and we'll continue to be one. That said, this role involves periodic onsite client visits — reliable transportation is a must.
6. Transparency – As part of the interview process, you'll have the opportunity to speak directly with other AM employees and get a real feel for what it's like to work here.

 

What You'll Be Doing

You'll serve as a principal technical resource across a portfolio of clients, contributing to their technology strategy and owning complex projects and escalations end-to-end. This is a collaborative role — you'll work closely with fellow engineers, L1/L2 technicians, and AM's CIO to deliver outcomes that matter. Most client engagements happen remotely, with onsite visits scheduled in advance for project work, executive meetings, and major cutovers.

Client Leadership and Strategy

• Serve as a fractional IT leader for assigned clients — owning technology roadmaps, annual budgets, and quarterly business reviews with executive stakeholders
• Translate complex technical concepts and risk into clear business language for non-technical audiences
• Lead client-facing conversations on compliance, security posture, and IT investment priorities
• Translate business requirements into technical architecture and multi-quarter project plans

Architecture and Project Delivery

• Design and lead implementation of complex projects: Microsoft 365 / Entra tenant design, Conditional Access and Zero Trust rollouts, Intune MDM/MAM deployments, server and network refreshes, cloud migrations, and M&A integrations
• Own the technical standards and reference architectures our team deploys against
• Lead security and compliance initiatives — SOC 2, CMMC/NIST 800-171, HIPAA — including policy development, control implementation, and audit support

Escalation and Technical Ownership

• Serve as the final escalation point for the most complex client issues — the engineer who owns the problem when nobody else can solve it
• Lead post-incident reviews and drive the remediation work that prevents repeat issues
• Own the deep-dive troubleshooting on identity, hybrid cloud, networking, and security problems

Team Collaboration and Mentorship

• Collaborate with fellow engineers and contribute to a culture of shared knowledge and continuous improvement
• Mentor L1 and L2 technicians through technical coaching and project shadowing
• Contribute to hiring, technical interviews, and onboarding of new engineers
• Drive continuous improvement of our internal documentation, runbooks, and tooling

What You Should Bring

Required Technical Depth

• Microsoft 365 / Entra ID — tenant architecture, hybrid identity, Conditional Access, Intune (MDM and MAM-WE), Defender suite, Purview/compliance, Exchange Online, SharePoint/OneDrive governance
• Identity and Access — Active Directory, Entra Connect, SSO/SAML/OIDC, privileged access management, phishing-resistant MFA (FIDO2, passkeys)
• Security Architecture — Zero Trust principles, endpoint protection (EDR/XDR), application allowlisting, email security, vulnerability management, incident response
• Networking — firewall administration (Meraki, Fortinet, SonicWall, or similar), VLAN design, VPN and SD-WAN, TCP/IP, DNS, DHCP, routing fundamentals
• Server and Virtualization — Windows Server (current versions), VMware or Hyper-V, storage (SAN/NAS), backup and DR architecture (Datto, Veeam, or similar)
• Cloud Platforms — Azure (required); AWS or GCP exposure a plus
• MSP Tooling — RMM platforms (Datto RMM, Kaseya, NinjaOne, or similar), PSA platforms (ConnectWise Manage, Autotask, HaloPSA, or similar), documentation systems (IT Glue, Hudu)
• Compliance Frameworks — working knowledge of at least one of SOC 2, CMMC/NIST 800-171, HIPAA, or PCI
• Scripting and Automation — PowerShell at a production level; Graph API, Power Automate, or similar a plus

Experience

• 8+ years in IT with at least 3 years in a lead engineer or equivalent hands-on technical capacity
• Prior MSP experience strongly preferred — you understand the cadence of multi-client work
• Demonstrated history of owning projects end-to-end, from discovery through handoff
• Experience developing IT roadmaps and technology budgets and presenting them to business stakeholders
• Experience mentoring junior technicians and contributing to team growth
• Relevant certifications are valued: Microsoft (MS-102, SC-300, AZ-104, AZ-305), CISSP, CISM, CCNP, or equivalent

Who You Are

• Comfortable leading executive conversations and translating technical risk into business language
• Strong written communication — you document what you do and explain decisions clearly
• Collaborative by nature — you make the people around you better and you build on the work of your team
• Background supporting or operating within small businesses, with strong multitasking skills and comfort in dynamic, lean environments.
• Takes pride in excellent work; thorough, detail-oriented, and follows through
• Maintains composure under pressure and handles concurrent priorities well
• Genuinely enjoys mentoring and sees team growth as part of the job

Benefits

• Base compensation: $100,000–$140,000 depending on experience and certifications
• Paid vacation: 15 days/year to start, increasing to 20 days after 3 years and 25 days after 5 years
• Paid sick time: 40 hours per annual year
• 9 paid holidays plus your birthday off
• Company-paid health insurance (Blue Shield PPO or Kaiser — your choice), dental, and vision; dependent coverage available at a significant company subsidy
• Life and short/long-term disability insurance
• Employee Assistance Program (EAP)
• Employee Anniversary Recognition Program
• Company-funded training materials and professional certification exams
• Mileage and vehicle wear-and-tear reimbursement for all client visits
• 401k with company matching (after 90 days)
• Virtual lab environment for self-directed learning and experimentation

We are an equal opportunity employer. This position is open to local Bay Area candidates only — no relocation benefits are available. Candidates must be authorized to work in the United States.