Technical Support Specialist

What we do Adaptive is a vertical AI company of 50, building the agentic operating system for the $2 trillion U.S. construction industry. We work with over 1,000 customers, partner with over 50 accounting firms, and have raised $26m from Emergence, a16z, and other top funds. Why join us? Win a massive category that's up for grabs. Construction is among the least digitized industries left, and no AI king has been crowned. With our momentum, team, and backing, we are in position to be that company Build a moat that compounds. We orchestrate multi-stakeholder workflows across an industry that today runs on paper, email, and phone calls. Every process we manage generates data no one else has. That data makes each new use case easier to expand to, while building a compounding moat Work with the rare team that can pull this off. Winning here takes deep construction knowledge and deep AI fluency in the same room. That intersection is rare, and we have it with backgrounds across finance, technology, and construction Serve the people building the world around you. Your favorite local café. The new house on the corner. The massive new skyscraper at Central Park South. All built by our customers: skilled, creative people who have spent their lives bringing neighborhoods to life Role Summary As a Technical Support Specialist at Adaptive, you’ll assist customers while also taking ownership of advanced technical investigations. In addition to real-time support, you’ll analyze logs, reproduce issues, diagnose integration failures, and determine whether problems stem from user workflows, data discrepancies, or product defects. This role acts as a critical bridge between Support and Engineering and provides a defined path toward becoming a Technical Support Engineer. Responsibilities Handle customer support inquiries, including advanced technical issues requiring deeper analysis Review logs, metadata, and internal dashboards to diagnose complex problems Replicate customer-reported issues in sandbox environments Troubleshoot integrations, with a strong emphasis on QuickBooks Online (QBO) sync behavior Assess whether issues represent bugs, user errors, or workflow misunderstandings Create clear, detailed escalation tickets for engineering with reproduction steps, logs, impact, and hypotheses Manage multi-step investigations, ensuring timely follow-up with customers Collaborate with engineering during escalations to provide context and add technical findings Surface patterns and recurring issues in Product and Engineering Produce detailed Help Center content focused on technical troubleshooting and integrations Qualifications 2+ years technical support, tier-2 support, or SaaS troubleshooting experience Required: Experience with QuickBooks Online Strong debugging skills and comfort working with logs, data, and test environments Excellent written communication for investigations and engineering escalations Experience handling long-running technical cases General understanding of construction industry financial processes (or aptitude for quick learning) Familiarity with customer communication platforms like Intercom Demonstrated ability to learn complex systems and processes quickly What We Offer Opportunity to take on high-impact technical work Competitive cash compensation Top-tier benefits and 401(k) match Flexible, remote-friendly work environment This role requires you to be based in the United States and authorized to work in the U.S.