Senior Technical Advisor

We’re looking for a Senior Tech Advisor who can combine strong MSP delivery with client-facing confidence and practical cybersecurity advisory experience. You’ll be successful if you enjoy owning outcomes end-to-end, communicating with empathy, and staying hands-on while improving the way we work.Experience: 3+ years of MSP experience, with proven ability to support multiple client environments.Admin expertise: hands-on Microsoft 365 administration and Google Workspace administration experience.Client-facing strength: proven experience working directly with clients—building trust, setting expectations, and translating technical issues into clear next steps.Cybersecurity advisory: solid, practical background in cybersecurity advisory (e.g., assessing risk, recommending controls, and guiding implementation).Escalation leadership: confident ownership of L2 escalations, including structured troubleshooting and decisive resolution.Mentorship: willingness and ability to mentor a service desk technician and raise the bar on documentation and processes.Soft skills: strong communication, accountability, proactive problem-solving, and a collaborative mindset in a remote team environment.Location fit: Argentina or Colombia based (preferred) to support our remote working model. Serve as the L2 escalation point for our service desk, diagnosing and resolving complex incidents and requests across client environments.Own client relationships independently: lead structured check-ins, communicate technical findings clearly, and ensure action items are closed.Deliver cybersecurity advisory support by identifying risk, recommending controls, and helping clients implement safer configurations and processes.Advise on configuration, identity, endpoint, email, backup, and security workflows to improve reliability and reduce recurring issues.Mentor and coach the service desk technician, sharing troubleshooting approaches, documentation standards, and escalation playbooks.Collaborate with internal teams to continuously improve support quality, documentation, and customer success outcomes. At Tsquared, we’re a close-knit team dedicated to helping accounting firms with their technology needs. We support tech-forward accounting firms and SMBs across the US as a modern, fully remote MSP. In this role, we’ll place the Senior Tech Advisor at the center of our customer outcomes: guiding clients through complex technical situations, advising on cybersecurity posture, and ensuring our service desk escalations are resolved with clarity and accountability. You’ll own relationships independently for assigned clients, provide L2 escalation support, and help shape best practices that improve delivery, uptime, and security across the portfolio. 100% remoteCompetitive USD compensationPaid time offCompensated local holidaysReal growth opportunities as we scaleA small, collaborative team that has your backWork with cutting-edge cybersecurity tools and tech-forward clients Experience supporting accounting firms, professional services, or regulated organizations.Familiarity with common MSP tooling (ticketing, monitoring, remote management) and best practices for incident management.Background in security implementation work such as MFA rollouts, conditional access guidance, email security hardening, backup verification, and security awareness enablement.Comfort creating and maintaining client-ready documentation, runbooks, and technical reports.Certifications or equivalent proof of knowledge in Microsoft, Google, or cybersecurity.