Technical Support Specialist

Adaptive is a rapidly growing vertical AI company of 40, building an AI-native ERP for real estate and construction. We have grown rapidly to over 600 customers and have raised $26m from Emergence, a16z, and other top funds, as well as a collection of angels from companies like Brex, Ramp, Airbase, Square, and Shopify.

We serve the small businesses that are building communities across our country. Your favorite local café, the new house on the corner, or the ADUs helping to solve the housing crisis were all built by our customers--those who have lived in their cities for their entire lives and have a true passion for their craft. These are creative, dynamic, skilled individuals who bring neighborhoods to life by conceiving of and constructing environments where people connect and build memories.

We have built a culture rooted in collaboration, execution, and experience! We have deep backgrounds in finance, technology, and construction, and a fast-growing customer base. We have the momentum, team, and vision to win in this massive market. We'd love for you to join us.

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.

• 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

• 2+ years technical support, tier-2 support, or SaaS troubleshooting experience

• Required: Experience with QBO or other accounting system integrations

• 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

• Opportunity to take on high-impact technical work

• Competitive cash compensation

• Top-tier benefits and 401(k) match

• Flexible, remote-friendly work environment

The annual base compensation range for this role is $70-75k USD plus top-tier equity and benefits.