Full Time
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40
Dec 15, 2025
Job Title: Technical Customer Support Specialist
Location: Remote (Work from anywhere!)
Company: Maestro Labs
About Maestro Labs:
At Maestro Labs, we’re building the future of AI-driven productivity tools. Our flagship product, MailMaestro, helps professionals create high-quality
Backed by global industry leaders (including the co-founder of Lightspeed Ventures, exChairman of Microsoft and senior partners from BCG), our team is made up of passionate innovators from top companies like Amazon, Uber, DoorDash, Kraken, and more. As we continue to scale, we’re looking for a Technical Customer Support Specialist to join our close-knit team and help educate users about our AI plug-ins for Microsoft 365, Outlook, and Teams. This is your chance to directly impact our growth and work closely with the CEO and other senior leaders.
What You'll Be Doing:
• Customer-Centric Support: Provide high-quality technical support to users of our Microsoft 365, Outlook, and Teams integrations, ensuring they get the most out of our AI tools.
• Troubleshooting & Resolution: Tackle technical challenges related to Microsoft applications and provide solutions that delight customers.
• AI Expertise: Help customers optimize and configure their Microsoft environments with our AI-powered plug-ins.
• Jumping on Customer Calls: Join live customer calls to provide hands-on support, troubleshoot issues in real time, and build strong relationships through direct engagement.
• Collaboration with Teams: Work cross-functionally with internal teams to escalate and resolve complex issues, offering valuable feedback to improve the product.
• Proactive Solutions: Document support cases clearly, and provide proactive recommendations to enhance customer productivity with Microsoft tools.
• Work Directly with the CTO: Collaborate closely with our CTO to align customer feedback with our product vision and drive strategic decisions.
What We’re Looking For:
• Experience: 4-5 years in a technical support role, especially in the Microsoft ecosystem.
• Technical Know-How: Expertise with Microsoft 365, Outlook, and Teams, including troubleshooting and system configuration.
• Communication Skills: You can explain complex technical concepts to both technical and non-technical users in a clear, • friendly manner.
• Problem-Solver: Strong analytical and troubleshooting skills with a passion for helping customers succeed.
• Self-Starter: Ability to work independently and take ownership of tasks in a fast-paced, growing company.
Bonus Points for:
• Experience managing subscriptions and invoices with Stripe.
• Familiarity with additional Microsoft 365 tools and services.
• Previous experience in customer-facing or technical support roles.
Why Maestro Labs?
• Direct Impact: Work directly with the CTO and key leadership to shape the future of our AI-driven products.
• High Autonomy: Enjoy the freedom to work on projects that matter and take ownership of your work. You d
• Global Team: Be part of a small, innovative team (~10 people) distributed across 8 countries. Work with people from diverse backgrounds who value your input and creativity.
• Career Growth: Access to ongoing training and conferences to help you level up your skills.
• Remote-First Culture: Enjoy the flexibility of working from anywhere while collaborating with a distributed, global team.
• Be at the Cutting Edge: Join a fast-growing AI startup with some of the brightest minds in tech, including ex-Amazon, Uber, and Doordash engineers, as well as consultants from BCG and other top firms.
How to Apply:
Ready to join the Maestro Labs team? Send your CV to
Our Commitment:
We are an equal opportunity employer and celebrate diversity in all its forms. We encourage candidates from all backgrounds to apply.