AI-First Technical Success Engineer

DataGrail, Inc.; Northern (KY); Hybrid; USD 80,000 - 100,000; Full time

Benefits offered by this job

Equity

Health insurance

Dental insurance

Vision insurance

Remote-first environment

401(k) savings plan

Parental leave

Wellness benefits

Flexible time off

Paid holidays

Work from home stipend

Job summary

DataGrail, Inc. is seeking a Technical Success Engineer to be the first line of contact for support questions, investigate bugs, and work with Success, Product and Engineering to ensure successful technical implementation. You’ll document issues, keep public docs up to date, and help customers using Claude tools in an AI-first environment.

This remote-friendly role offers equity and comprehensive benefits, with a compensation range explicitly stated for US-based postings.

Qualifications

• Strong technical background from an engineering, technical support, or implementation role.
• Familiarity with at least one programming language, ideally Ruby on Rails, with the ability to write scripts to diagnose issues.
• Ability to reproduce an issue, gather technical context from a non-technical customer, and dig through logs to paint a complete picture for Engineering.
• Strong written communicator, comfortable working directly with customers via email or Zoom, able to translate technical issues into clear guidance for both customers and engineers.
• Comfortable being pulled in multiple directions at once, able to multitask and shift between competing high-priority issues throughout the day.
• Comfortable operating in ambiguity, asking good questions, and experimenting with new approaches as the support function matures.
• An AI-first mindset: you use tools like Claude and Claude Code daily and contribute to the shared AI workflows and processes that help the whole team move faster.
• A habit of flagging process or tooling improvements when you spot a recurring problem.

Responsibilities

• Serve as DataGrail's tier 1 technical support, resolving requests directly and flagging what needs deeper expertise.
• Investigate and reproduce reported bugs, then elevate to Engineering with clear repro steps and context.
• Facilitate the back-and-forth between Engineering and the customer, and close the loop once a fix or workaround ships.
• Partner with Customer Success to ensure successful technical implementation for customers.
• Keep DataGrail's public documentation up to date.
• Identify recurring patterns in support tickets to help improve processes and documentation, enabling customers to self-serve enablement and troubleshooting as much as possible, and helping drive down resolution time and key SLAs.
• Contribute to DataGrail's AI-first workflows, helping build and improve the shared tools, prompts, and processes that help the team move faster.
• Partner closely with Product and Engineering, surfacing what's blocking customers in the product and feeding that insight into upcoming features.

Skills

Ruby on Rails

Technical support

Issue diagnosis

Customer communication

Multitasking

Ambiguity tolerance

AI workflows

Proactive improvement

Tools

Rest APIs

SAML

SSO

Datadog

Sentry

AWS

SQL

Job description

DataGrail, Inc. is seeking a Technical Success Engineer to be the first line of contact for support questions, investigate bugs, and work with Success, Product and Engineering to ensure successful technical implementation. You’ll document issues, keep public docs up to date, and help customers using Claude tools in an AI-first environment.

This remote-friendly role offers equity and comprehensive benefits, with a compensation range explicitly stated for US-based postings.