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About the Role
Serve as the primary technical contact for enterprise accounts, owning the technical health of AI deployments end-to-end. You will troubleshoot AI issues, refine prompts, analyze data, and communicate technical details to customers in plain language, acting as a liaison between product, engineering, and customer success.
Responsibilities
- Serve as the primary technical contact for a small portfolio of enterprise accounts, joining regular customer calls, owning follow-through, and building trusted relationships with stakeholders
- Troubleshoot conversational AI behavior through prompt engineering: diagnose why the assistant responded a certain way, then iterate on system prompts, escalation flows, and knowledge sources to fix it
- Review voice and chat conversation logs to identify failure patterns, quality gaps, and improvement opportunities
- Configure, monitor, and troubleshoot Manager AI back-office automations — diagnosing where workflows break down and getting them back on track
- Support integrations between STAN and each customer's property management system (PMS) and enterprise applications — APIs, data flows, and debugging across the stack
- Run data analysis on conversation and automation outcomes — resolution rates, escalation rates, ticket quality — and turn findings into clear, decision-ready reporting for customers and internal teams
- Explain complex technical situations to non-technical stakeholders: root causes, tradeoffs, and timelines, delivered clearly and credibly
- Translate customer feedback and recurring issues into structured product input for engineering
Requirements
- 3+ years in SaaS (preferred), ideally in professional services, technical account management, solutions engineering, or a forward-deployed engineering role
- Real technical depth with AI/LLM-based products: you understand how prompts, context, and model behavior interact, and you troubleshoot systematically rather than by guesswork
- Basic backend engineering skills — comfortable with APIs, webhooks, reading logs, querying data (SQL), and light scripting (Python or similar)
- Strong analytical instincts: you can take raw conversation or ticket data and produce a defensible read on what's actually happening
- Excellent client-facing communication — calm under pressure, credible with executives, precise without jargon
- Ownership mentality: you close loops, flag risks early, and are comfortable being the accountable name on an enterprise relationship
- Experience with conversational AI, voice AI, or contact center technology
- Workflow automation or systems integration experience
- Exposure to property management software (Yardi, AppFolio, Vantaca, CINC) or the HOA/community management industry
- Prompt engineering experience in a production environment
Skills
- Prompt engineering
- API
- Webhooks
- SQL
- Python
- Data analysis
- Client-facing communication
- Conversational AI
- Voice AI
- Contact center technology
- Workflow automation
- Systems integration
- Property management software
- HOA/community management industry
Experience Level
- 3+ years
Benefits
- Competitive salary
- Comprehensive health, dental, and specialist benefits
- Company Macbook
- Free parking and shuttle service to the office
- Extra PTO during occasional US holidays
- Company events, in-office restaurant, and building-wide perks
- Unlimited ping pong and espresso
About the Company
- STAN is the largest provider of AI solutions for HOA and Condo Property Managers.
- We are using cutting-edge and patented artificial intelligence technology to build solutions that enhance life for residents of more than 2.5 million+ homes across North America.
- We are on a mission to build the world’s first AI property manager.
- STAN is also an award-winning platform, having been recognized by Rogers, FedEx, George Brown College, StartUp Canada, the Waterloo Accelerator Centre, and more!