Job Description

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 added technical findings
Surface patterns and recurring issues to 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

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About Adaptive

We’re rebuilding the financial stack for the built world so builders can spend less time in spreadsheets and more time building hospitals, schools, and neighborhoods. Walk any Main Street in America and you’ll see our customers’ work: the corner cafe, the community theater revamp, an epic new skyscraper. Behind every project is a finance team buried in pay apps, hunting down job costs, and sitting through status meetings just to understand where budgets stand. We're building the first AI-native platform to fix this. We're building the first AI-native platform to fix this. Since launching in 2023, we've grown rapidly to ~1,000 customers, and have built partnerships with 6 of the top 100 CPA firms. We've also raised $26m from Emergence, a16z, and the operators behind Brex, Ramp, Square, and Shopify. We value diligence, creativity, urgency, and teamwork. If that sounds like you, and you are excited by the opportunity to reshape this massive, consequential industry, we'd love to meet you. Check out our open roles at: https://jobs.ashbyhq.com/Adaptive

Technical Support Specialist