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Added 13 mins ago
DW
Assistant Manager Quality Assurance
Durabuilt Windows & Doors
AB · Edmonton, AB
- Full-time
The Quality Assurance Assistant Manager supports the execution and continuous improvement of the Quality Management System (QMS), ensuring product quality, regulatory compliance, and…
Added 13 mins ago
NS
Rehabilitation Assistant - Rehabilitation Services
Nova Scotia Health Authority
Sydney Indian Reserve No. 28A, NS · Sydney, NS
- Internship
Under the direction of the Manager, and under the supervision of therapists, the Rehabilitation Assistant, as an active member of the patient care team, works with individuals, families and…
Added 13 mins ago
PT
EA1 (#316-PC)
Pembina Trails School Division
Winnipeg, MB
- Full-time
Employment Classification: Educational Assistant 1 (EA1)
Added 13 mins ago
PT
EA1 (#315-WG)
Pembina Trails School Division
Winnipeg, MB
- Full-time
Employment Classification: Educational Assistant 1 (EA1)
Added 13 mins ago
NS
Physiotherapist - Rehabilitation Services
Nova Scotia Health Authority
Truro, NS
- Full-time
Added 29 mins ago
OH
Medical Assistant - Olathe and Offsite Clinic Locations
Olathe Health
Pavilion 1, BC
- Full-time
The Medical Assistant is responsible for ensuring efficient flow of patients through the health care setting by facilitating examination and treatment of patients in a culturally sensitive…
Added 29 mins ago
UO
Program Manager, Workforce Development & Employer Engagement, UC Clermont College
University of Cincinnati
Clermont, QC
- Full-time
Under the direction of the Assistant Dean of Student & Graduate Pathways, support UC Clermont’s workforce development efforts through employer relationship management, work-based learning…
Added 29 mins ago
HS
Education Assistant - CARE Campus
Holy Spirit Catholic School Division
Lethbridge, AB
- Part-time
We are looking to hire a temporary 28.0 hour per week Education Assistant at the Centre for Adolescent Responsibility Education (CARE) Campus in Lethbridge. This assignment is to commence…
Added 29 mins ago
HS
Early Learning Education Assistant - Our Lady of the Assumption School
Holy Spirit Catholic School Division
Lethbridge, AB
- Part-time
EARLY LEARNING EDUCATION ASSISTANT – Our Lady of the Assumption School
Added 29 mins ago
C
Office Manager & Executive Assistant to the CEO
Clearspace
Toronto, ON
- Full-time
We’re looking for a highly organized, proactive, and people-oriented Office Manager / Executive Assistant to support both the day-to-day operations of our office and the CEO at Clearspace.
Added 59 mins ago
WB
Assistant Manager: Mountain Safety - Salary
Whistler Blackcomb
Whistler, BC
- Temporary
Added 59 mins ago
WC
Full Time Pharmacy Assistant - Courtenay
Walmart Canada
Courtenay, BC
- Full-time
Position Summary...The Pharmacy Assistant assists the Pharmacist in the technical aspects of prescription filling and administrative duties in order to increase the Pharmacist's opportunity…
Added 59 mins ago
WC
(CAN) Overnight Assistant Manager
Walmart Canada
Alma, QC
- Full-time
…Operations - specific area that the incumbent will oversee). An Assistant Manager is cross-trained to work proficiently in all areas of the Store when…
Added 59 mins ago
WC
(CAN) Leader de nuit
Walmart Canada
Sainte-Agathe-des-Monts, QC
- Full-time
Assists in providing direction and coordinating overnight stocking activities based on communicated priorities from the Overnight Assistant Manager and the daytime management team.
Added 59 mins ago
TS
Assistant Project Manager – ICI Construction
TalentSphere Staffing Solutions
Peterborough, ON
- Full-time
…Commercial and Industrial (ICI) construction, is seeking an Assistant Project Manager for a major ground-up commercial construction project in…
Added 59 mins ago
C&
Administrative Assistant
Christensen & McLean Roofing Co. Ltd.
AB · Edmonton, AB
- Full-time
Added 59 mins ago
T
Legal Assistant
TEEMA
Vancouver, BC
- $60,000 to $85,000 CAD / year
- Full-time
Minimum one year of experience as a legal administrative assistant.
Added 59 mins ago
SD
Pharmacy Assistant, Hourly Part Time Day Greenlight Requisition
Shoppers Drug Mart
Abbotsford, BC
- Part-time
Diploma from a Pharmacy Assistant credited course preferred
Added 59 mins ago
SD
Merchandiser, Hourly Part Time Flexible Shifts
Shoppers Drug Mart
Mississauga, ON
- Part-time
Supports Front Store Manager/Assistant Front Store Manager in maintaining the quality and standards
Added 59 mins ago
SD
Assistant Front Store Manager, Hourly Full Time Flexible Shifts Greenlight Requisition
Shoppers Drug Mart
Calgary, AB
- Full-time
Added 59 mins ago
SD
Assistant Front Store Manager, Hourly Full Time Day Greenlight Requisition
Shoppers Drug Mart
Toronto, ON
- Full-time
Added 59 mins ago
SD
Pharmacy Assistant, Hourly Full Time Day Greenlight Requisition
Shoppers Drug Mart
Kelowna, BC
- Full-time
Diploma from a Pharmacy Assistant credited course preferred
Added 59 mins ago
VP
Healthcare Professional SME - AI Evaluator
Volga Partners
Remote, Canada
- Other
- Remote
…Medicine, Internal Medicine, Nurse Practitioner, or Physician Assistant…
Added 59 mins ago
E
Territory Representative, Hospitality Sales & Service
Ecolab
Mississauga, ON · Richmond Hill, ON · Toronto, ON · Woodbridge, ON · ON
- Full-time
Added 1 hour ago
TA
English Language Arts Teacher
Think Academy US
Toronto, ON
- $3,500 CAD / month
Prior tutoring, teaching assistant, or other student-facing teaching experience is strongly preferred.

Leo Toronto

Conversation Designer (Freelance)

Canada

Part-time

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Applications open in a new tab.

Job details

Job type: Part-time
Posting language: English
Posted: Nov 5, 2026

Original job description

CONTRACT CONDITIONS:

Commitment About 1.5 days a week (roughly 10–11 hours,

based on 7-hour days)

Length 6 weeks, Nov. 9 to Dec. 18, 2026

Remote or Hybrid Toronto - EST time

Leo Toronto is a creative advertising agency within the global Leo network. The agency partners with major brands to develop creative ideas and campaigns, bringing together strategy, creativity, design and production.

THE PROJECT

We're a small team embedded with a large consumer tech client, working on an AI assistant in the health and wellness space. Instead of only replying with text, the agent decides when to show interactive UI, like cards, comparisons or planners, right in the chat. In the last round we built this as a working prototype with a real model behind it.

This round is about finding out which of those tools people actually want, and what the assistant needs to earn a bigger role. Over six weeks we'll put real tools in front of real people across two rounds of testing, and turn what works into a defined system.

WHAT YOU'LL DO

Shape the agent people talk to in testing. Write and tune the prompts, tool descriptions and behaviour rules that decide when each tool shows up.
Design the moments that matter most: onboarding, when the agent asks for personal information, and when one assistant should hand the conversation to another.
Map edge cases for the core tools: the golden path, ambiguous intent, and the fallback at each step.
Observe user testing sessions and fold what we learn back into the design.
Join daily syncs with the client. A lot of the value is in those conversations: pressure-testing ideas, flagging risks early, and helping the client make calls.
Work closely with our UX designer and creative technologist, who build your thinking into a working prototype every Friday.

WHAT WE'RE LOOKING FOR

You've designed conversational or agentic experiences on top of LLMs, and you've done it with clients. You walk a client through trade-offs and help them land a decision, not just hand over a flow.
You think in edge cases. You 're the person who asks "and what if they say this?" and then writes down the answer.
You're comfortable writing and editing prompts, tool descriptions and behaviour rules, not only sample dialogue.
You're happy working scrappy. Work in progress over polished decks.

Why generative UI matters here. It's a paradigm that's hard for a lot of people to wrap their heads around. Part of this role is helping the client think in it, so the more you've lived it, the better.

NICE TO HAVE

Experience with health or wellness products
Working with Claude or other models directly, or reading prompts in a codebase
Experience sitting in on user research and turning findings into design changes
Multi-agent experiences, where one assistant hands off to another

HOW TO APPLY

Send us your resume and a short note that covers:

1. Start with your AI product example, in two or three sentences: what the product was, what the model did beyond chat, and what you designed.

A link to the work: a flow, edge-case map, prompt or behaviour rules you wrote.

We'll only be able to review applications that include an example of AI product beyond a basic chat app.

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More about this job

Responsibilities

Design and refine the AI assistant’s prompts, tool descriptions, behavior rules, and key conversational moments, including onboarding, personal information requests, and assistant handoffs. Map core-tool edge cases, observe user testing, incorporate findings, and collaborate with the client and prototype team to shape a defined system.

Requirements

Applicants should have designed LLM-based conversational or agentic experiences with clients and be able to guide client decisions through trade-offs. They should be comfortable writing prompts, tool descriptions, and behavior rules, mapping edge cases, and working iteratively; experience with generative UI is especially valuable.

Skills

Conversation Design
LLM Prompt Writing
Agentic Experience Design
Generative UI
Tool Description Writing
Behavior Rule Design
Edge-Case Mapping
User Testing
User Research
Client Communication
Health and Wellness Product Design
Multi-Agent Experience Design
Prototype Collaboration

Visa sponsorship

Not detected in the job text

Keywords

LLM
AI Assistant
Agentic Experiences
Generative UI
Conversation Design
Prompt Writing
Tool Descriptions
Behavior Rules
Interactive UI
Health and Wellness
Onboarding
Personal Information
Assistant Handoffs
Edge Cases
User Testing
User Research
Prototype
Claude
Multi-Agent Experiences
Client Collaboration

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