Product Support Specialist II
Job Description
About SpotDraft
SpotDraft is on a mission to help legal and business teams move faster, together. Our AI-powered contracting platform is redefining how companies manage contracts, and our story deserves to be told in creative, human, and memorable ways.
Top Outcomes:
The Product Support Specialist II is the technical backbone of the Support team. You sit at the intersection of product depth, integration expertise, and pattern intelligence, resolving what L1 cannot, training the team to close the gap, and converting recurring problems into structured signals for Engineering and Product.
Day to Day:
OWN THE HARD STUFF
Complex UI Config
Handle advanced workflow configuration including Conditional Approvals, multi-step UI setups, and edge-case config scenarios that L1 cannot resolve.
OOB Integrations - Setup, configure, debug, and isolate log-level issues for all core out-of-the-box integrations, end to end.
API and Webhooks - full knowledge and debugging: HTTP errors, payload inspection, response analysis, and integration-level root cause isolation.
CLM Log analysis - read and work with internal CLM logs to isolate issues before escalating to Engineering.
Advanced tooling - Metabase (joins, custom logic), DataDog, HAR, Groundcover, GCP log analysis. You pick the right tool for the job.
Template changes and computations - execute basic template change requests and read, modify, and validate template computation logic accurately.
BE THE PATTERN ENGINE
Spot recurring issues across ticket volume before they become systemic - your job is to see the signal before leadership asks for it.
Hand off patterns as structured, evidence-backed submissions to Product and Engineering - not Slack messages, not verbal flags. Documented, prioritised, traceable.
Own special projects delegated by your Manager - deliver end-to-end with no hand-holding required.
MULTIPLY THE TEAM
Train new joiners to L1 operational standard within expected ramp timelines - you own their technical onboarding.
Write, update, and improve Help Articles based on what you learn from tickets - your KB contributions should reduce repeat questions over time.
Guide L1s informally through KT sessions and pair troubleshooting - minimum twice a month. You are expected to be available and useful, not just available.
PUSH AI FURTHER THAN L1 DOES
Expert AI literacy — advanced prompting, multi-step context management, critical evaluation of model output. You know when to trust it and when not to.
MCP servers — not just familiar, expert. Integrated into your debugging and escalation workflow as standard practice.
Ensure KB articles you author are structured for AI retrieval accuracy — not just readable by humans. You understand that what you write may be used to train or inform AI responses.
Coach L1s on AI usage quality — what to review, what to override, what to flag. You are the AI quality bar for your pod.
Requirements:
Experience:
3+ years as a Product Support Specialist, Product Support Engineer, or equivalent in a B2B SaaS environment. You must have operated at L1 level and be ready to demonstrate it.
Integration depth:
Hands-on experience setting up and troubleshooting OOB integrations and connectors — not just familiarity. You have debugged integration failures at log level and owned the resolution.
API and technical fluency:
Deep understanding of HTTP error codes, API request/response cycles, webhook behaviour, and payload inspection. You have debugged API issues without Engineering holding your hand.
Log analysis tooling:
Proficient in DataDog, HAR, Groundcover, GCP, and Metabase — joins, filters, custom queries. You use these to isolate root cause, not just to check if something is broken.
Template and computation literacy:
Ability to read, understand, and modify template logic and computation structures. Errors in your template work should be rare — not a recurring pattern.
AI and MCP expertise:
Expert-level use of LLM tools and MCP servers as daily workflow tools. Prompt engineering at depth, output evaluation, and the judgment to know when AI is wrong. This is beyond awareness — it's fluency.
Pattern recognition and communication:
Ability to synthesise patterns across tickets and communicate them with precision, structured, evidence-backed, and actionable. Not every problem is a signal, and you know the difference.
Coaching instinct:
You can train and guide junior team members without being asked twice. You find it natural to share knowledge, and people actually learn from you.
Communication standard:
Impeccable written communication. Confident working with senior stakeholders at large enterprise accounts. You write with precision and adapt your tone to context.
Flexibility:
Willingness to work in a 24/7 support environment across coverage windows.
Why SpotDraft?
Brilliant teammates—Work with some of the sharpest minds in legal tech.
Expand your network—Interact with top founders, investors, and industry leaders.
Real impact—Take ownership of projects and see your work in action.
Big goals, bold moves—We trust you to deliver, innovate, and push boundaries.
Our Core Values
Our business is to delight Customers
Be Transparent. Be Direct
Be Audacious
Outcomes over everything else
Elevate each other
Be Passionate. Take Ownership.
Be 1% better every day
All candidates’ personal data shared during the recruitment process will be handled with utmost confidentiality and used solely for hiring purposes, in line with applicable data protection regulations.
*SpotDraft is an equal-opportunity employer. Candidates will not be discriminated against based on race, ethnicity, color, religion, caste, sex, gender identity, sexual orientation, national origin, veteran, or disability status