About Summit
Building the commercial brokerage of the future. Summit is a boutique commercial insurance firm headquartered in Kelowna and serving businesses across Canada. We are a venture-backed, tech-enabled commercial insurance brokerage redefining what it means to be a modern insurance partner. With strong values—Sustainability, Ownership, Transparency, and Impact—we move fast, support one another, and raise the bar for industry standards.
Summit is a team of empowered and high-performing individuals who live our core values every day. Being a part of Summit offers a chance for the right applicant to make a name for themselves, and help build Summit as a leader in the Canadian Commercial Insurance market.
Summit's brokers handle commercial insurance for businesses across Canada — and increasingly, they don't do that work alone. Inside Synapse, our internal agent platform, a fleet of 15+ production AI agents now handles the technical heavy-lifting that used to consume their week: risk assessments, COI generation, binder issuance, proposals, renewal comparisons, policy verification, group benefits reports. When those agents work, brokers move faster, clients get sharper analysis, and Summit ships work that wouldn't otherwise exist. We're hiring an AI Operations & Quality Engineer to make sure they keep working and to keep raising the bar on what they can do.
About the role
Agent Quality Assurance
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Run regression tests against canonical scenarios for every production agent — catch drift, broken outputs, and edge cases before brokers see them.
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Design and calibrate evaluation rubrics for each agent's deliverables and analyze score patterns to flag systemic issues.
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Reproduce failed runs surfaced by brokers, root-cause them, and ship fixes via memory updates, skill edits, or prompt revisions.
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Audit branded deliverables for brand compliance, verifying compliance across fonts, logos, layouts, and data structure.
Skills, Memories, and Prompts
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Curate the memory library inside Synapse: dedupe, retire stale facts, tune importance and "when to use" routing so agents pull the right context.
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Author new skills (documented playbooks + Python scripts) that turn repeatable workflows into reusable agent capabilities, with credential handling and verified outputs.
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Iterate on agent system prompts and sub-agent personas; keeping them tight, testable, and aligned with how brokers actually phrase requests.
Model & Cost Optimization
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Monitor model spend across the agent fleet and tune model selection (Opus / Sonnet / Haiku and sub-agent defaults) to balance quality, latency, and cost.
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Identify hot spots — agents over-spending on simple problems, or under-spending on hard ones, and rebalance.
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Track token usage, latency, and error rates over time; publish a weekly fleet health report for the team.
Working with Brokers
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Embed yourself with broker teams, when their requests surface bugs or feature gaps, you turn that intel directly into roadmap items.
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Partner with our agent builders on every new agent. Review specs, design test plans, and sign off on launches.
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Document agent capabilities, known limitations, and broker-facing workflows so AEs and brokers can use the fleet confidently.
Skills & Qualifications
Must-Haves:
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2-4 years working hands-on with LLM-powered applications, AI agents, or production prompt-engineered systems (formal CS degree not required if your project work demonstrates the skill set).
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Strong instinct for prompt engineering. You can read a system prompt and explain why an agent is misbehaving.
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Comfort writing Python at a scripting level (API calls, JSON manipulation, light data transformation) — you'll be authoring skill scripts.
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Experience designing test cases and evaluation criteria for non-deterministic systems, or a clear conceptual framework for doing so.
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Sharp diagnostic instincts: when an agent misfires, you can trace whether the issue lives in the memory, the skill, the prompt, the model, or the input.
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Strong written communication — you'll translate "this agent broke" into a clean diagnosis and a fix log the rest of the team can act on.
Nice-to-Haves:
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Hands-on experience with Anthropic's Claude or comparable frontier models (Opus / Sonnet / Haiku tier selection).
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Familiarity with evaluation frameworks and rubric-based grading.
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Insurance, financial services, or other regulated-document workflows where output accuracy is non-negotiable.
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Exposure to HubSpot CRM, Slack, and Google Workspace as everyday operational tools.
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Background in high-growth startups or AI-forward operations teams.
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30 days — You've shadowed every production agent on a real broker run, mapped each one's known failure modes, and stood up a regression test suite for the top 5.
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60 days — You've shipped your first round of memory cleanups, retired stale skills, and authored at least one new skill end-to-end.
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90 days — You're running a weekly fleet health review, model spend is trending down without quality regression, and broker-reported bugs have a clear triage and resolution path.
Perks We Offer at Summit
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Opportunity for Growth: Work with a forward-thinking commercial brokerage and be part of an innovative, growing team.
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Modern Workspace: Work from our brand-new, state-of-the-art offices in downtown Kelowna and Winnipeg. Enjoy a flexible hybrid model designed to support collaboration, focus, and balance.
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Technology-Driven Culture: Work with cutting-edge tools and custom built technology to get time back in your day. Laptops & equipment provided to all staff.
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Comprehensive Benefits: Access to flexible health, mental health, dental plans tailored to your lifestyle, and competitive vacation and personal day allotments.
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Supportive Team: Participate in daily team huddles and collaborative events as part of a values-driven culture.
Our Values
At Summit, our values guide everything we do:
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Transparency: We build trust through open and honest communication.
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Sustainability: We create lasting solutions for our team, partnerships, and communities.
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Ownership: We take accountability for our actions, celebrate victories, and learn from mistakes.
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Impact: We think big and aim to make a difference in everything we do, both in business and for social good.
If you’re ready to take the next step in your career and help build a new-age commercial insurance brokerage, we want to hear from you.
OTE: $80,000-$120,000
Summit is an inclusive employer that celebrates diversity. We encourage applications from all qualified candidates and are committed to providing accommodations during the hiring process. While we thank all applicants for their interest, only those selected for an interview will be contacted.
Join us in building the commercial brokerage of the future!
