Senior AI Engineer

Guidepoint
Toronto, Canada
Hybrid

Who this role is best for

Strong fit for candidates who build and scale real-time conversational AI systems and have experience with LLM orchestration, who are based in Toronto and comfortable with hybrid work arrangements.

Best fit for

  • Candidates with experience shipping LLM-powered products in production and designing scalable real-time systems
    — “6+ years of software engineering, with 2+ years building LLM-powered products in production”
  • Candidates who can bridge engineering and product, with a focus on structured outputs and behavioral guarantees
    — “Partner with product and compliance stakeholders to encode domain rules into the system”
  • Candidates with cloud-native deployment expertise, particularly in Kubernetes and Azure
    — “Own services end-to-end: design, implementation, deployment (Kubernetes/Azure), and operations”

Things to consider

  • Hybrid work arrangement requires regular presence in Toronto’s office
    — “This role is hybrid in our Toronto Office”
  • Candidates must be prepared to manage end-to-end systems, including real-time and latency-sensitive workloads
    — “Own services end-to-end: design, implementation, deployment (Kubernetes/Azure), and operations, including latency-sensitive real-time workloads”

How to stand out

  • Highlight experience with multi-channel session management and structured data integration
    — “Multi-channel session management: stateful user interactions that move seamlessly across channels”
  • Demonstrate ability to define and implement evaluation infrastructure for AI systems
    — “Build the eval loop and treat quality as a number: define metrics, run experiments, gate releases on them”
  • Showcase hands-on work with LLM frameworks and vendor agnostic integration methods
    — “Integrate third-party AI and voice vendors behind clean abstractions so providers stay swappable”
Pace · Fast PacedCollaboration · HighAutonomy · HighDecision Impact · Team

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • take working prototypes to production
  • shape the architecture as the product scope grows
  • own services end-to-end
Typical background
6+ years of software engineering2+ years building LLM-powered products in production

Skills & requirements

Required

Llm-powered ProductsReal-time Conversational AILLM OrchestrationMulti-channel Session ManagementRetrieval And GroundingEvaluation InfrastructureKubernetesAzureLLM PipelinesVector DatabasesAgent/llm Frameworks

Preferred

Voice AIKnowledge GraphsRegulated DomainsEvaluation Harnesses

Stack & domain

TypeScriptPythonWebsocketsWebrtcAudio PipelinesKubernetesAzureLanggraphLangchainCrewaiVector DatabasesEmbedding-based RetrievalLlm-powered ProductsRag/groundingStructured OutputsEval-driven IterationLeadershipCommunicationProblem-solvingTeamworkAIConversational AILLMReal-time VoiceRetrieval Over Large Proprietary Datasets

About the role

Original posting from Guidepoint via Greenhouse

Overview:

Guidepoint is investing in applied AI across its research platform. We're building conversational AI systems that interact with our global expert network at scale — combining real-time voice, LLM-driven orchestration, and retrieval over large proprietary datasets.

You'll be an early engineer on a new initiative: taking working prototypes to production and shaping the architecture as the product scope grows. This is a hands-on role with broad ownership, close to product and leadership.

This role is hybrid in our Toronto Office

What You'll Do:

Real-time conversational AI: voice- and chat-based agents with low-latency requirements, built on modern telephony and real-time media infrastructure.

LLM orchestration: agentic systems that pursue goals over multi-turn conversations, with hard behavioral guarantees enforced in code — not just prompts.

Multi-channel session management: stateful user interactions that move seamlessly across channels.

Retrieval and grounding: connecting LLM systems to large internal knowledge assets, with structured data flowing back.

Evaluation infrastructure: measuring conversational quality against human baselines and gating rollouts on metrics, not vibes.

Own services end-to-end: design, implementation, deployment (Kubernetes/Azure), and operations, including latency-sensitive real-time workloads.

Design and tune LLM pipelines: context engineering, structured outputs, model selection, cost/latency tradeoffs across vendors.

Build the eval loop and treat quality as a number: define metrics, run experiments, gate releases on them.

Integrate third-party AI and voice vendors behind clean abstractions so providers stay swappable.

Partner with product and compliance stakeholders to encode domain rules into the system.

Set engineering patterns for a growing team: code review, observability, incident habits.

What You Have:

6+ years of software engineering, with 2+ years building LLM-powered products in production (not notebooks): orchestration, RAG/grounding, structured outputs, eval-driven iteration.

Strong TypeScript or Python; comfortable working across both.

Real-time or streaming systems experience: WebSockets, WebRTC, audio pipelines, or comparable low-latency work.

Cloud-native production experience: containers, Kubernetes, CI/CD, observability. Azure a plus.

Familiarity with agent/LLM frameworks such as LangGraph, LangChain, or CrewAI — hands-on exposure is enough; we care that you know the landscape and when plain code beats a framework.

Working familiarity with vector databases and embedding-based retrieval.

Pragmatic product judgment: you scope prototypes, kill weak approaches with data, and ship.

Nice-to-have:

Voice AI: telephony platforms, conversational agent frameworks, STT/TTS, turn-taking/VAD.

Knowledge graphs or large-scale search/retrieval systems.

Regulated or compliance-sensitive domains (healthcare, finance).

Eval harnesses or LLM-as-judge systems.

What We Offer: 

The annual base salary range for this position is 175,000-210,000 CAD. Additionally, this position is eligible for an annual discretionary bonus based on performance.

You will also be eligible for the following benefits:

Paid time off  

Comprehensive benefits plan  

Company RRSP match  

Development opportunities through the LinkedIn Learning platform 

About Guidepoint: 

Guidepoint powers end-to-end research workflows for the world’s best research teams.

Backed by a global network of more than 2 million experts and over 1,600 employees, Guidepoint delivers real-time access to expertise, primary research, and actionable knowledge that help organizations make informed decisions. Through consultations, surveys, events, proprietary content, and AI-enabled tools, we support every stage of the decision-making process—from developing hypotheses and gathering insights to validating assumptions and building conviction for critical decisions.

At Guidepoint, our success relies on the diversity of our employees, experts, and clients, which enables us to foster meaningful connections and a broad range of perspectives. We are committed to creating an inclusive and welcoming environment where individuals of all backgrounds, identities, and experiences can contribute and succeed.

#LI-LG1

#LI-HYBRID

This job posting is for an existing vacancy.  The salary offered will be based on the successful candidate’s skills, experience, qualifications, and location.

Compensation$175,000—$210,000 CAD

Source: Guidepoint careers (Greenhouse)

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