IT Technician (macOS, Google Workspace, Information Security)

The Opportunity Cascade is a premier Managed Service Provider (MSP) delivering world-class technical solutions to high-end Financial Services firms across the Bay Area, Los Angeles, and beyond. We are currently seeking a senior-level IT Technician who excels at the intersection of technical mastery and elite client service. In this role, you aren’t just closing tickets; you are a trusted technical partner to VIP users. You will provide "white-glove" support on-site in San Francisco and remotely for clients globally. If you are hyper-reliable, thrive in high-stakes environments, and are looking for above-market compensation, we want to hear from you. Who You Are The Ultimate Professional: You possess a "no task too small, no challenge too big" attitude and maintain a calm, focused demeanor under pressure. A Mac Expert: You have deep, demonstrable experience supporting macOS in an enterprise environment (Jamf Pro experience is highly preferred). A Clear Communicator: You can translate complex technical issues into simple, actionable language for executive leadership. Growth-Minded: You take extreme ownership of your career and are eager to leverage our generous certification and training bonuses. Technical Qualifications 7+ years of progressive Help Desk or Desktop Support experience. Expert-level macOS support (PC/Windows experience is a valued plus). MDM Proficiency: Hands-on experience with Jamf Pro or similar platforms. Networking Fundamentals: Solid understanding of DHCP, DNS, VPN, and troubleshooting remote connectivity. Scripting: Basic familiarity with Bash or PowerShell to automate workflows. AV/Smart Home (Bonus): Experience with Crestron, Savant, or high-end conferencing systems. Key Responsibilities VIP Engagement: Act as the primary technical point of contact for high-net-worth individuals and executive teams. Problem Solving: Tackle a diverse, unpredictable range of challenges—from office-wide network optimizations to personalized tech setups for traveling VIPs. Project Leadership: Execute cutting-edge technical improvement projects and infrastructure upgrades. Documentation: Maintain pristine technical records and SOPs to ensure team-wide consistency. Availability: Provide flexible, on-call support as needed to ensure our clients never skip a beat (includes occasional after-hours/weekend work). Why Cascade? We offer a “big-tech” comparable benefits package with the agility and growth potential of a high-growth startup. Premium Health: 95% coverage for medical, dental, and vision premiums. Financial Future: 401(k) with competitive employer match. Monthly Stipends: $125 for Tech, $100 for Healthy Living, and up to $400 reimbursement for commuting expenses. Professional Development: Generous reimbursements and performance bonuses for earning new certifications. Flexibility: This is a hybrid role with a minimum of 3 days a week onsite and up to 2 days at home.