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Added 9 mins ago
TH
Part Time Front End Associate
The Home Depot Canada
Oakville, ON
- Part-time
Using the GET Involved approach to customer service, front-end associate greets each customer, engages them during the transaction and thanks the customer for their business.
Added 9 mins ago
TH
Flooring and Decor Sales Associate Part Time (COLLINGWOOD)
The Home Depot Canada
Collingwood, ON
- Part-time
…your total rewards may include: semi-annual bonuses tied to business performance; Deferred Profit-Sharing Program to assist with retirement savings; comprehensive paid benefits; a 15%…
Added 9 mins ago
OC
Senior Demand Planner - Service Parts
Olympus Corporation
Richmond Hill, ON
- Full-time
Own demand forecasts for service parts using historical consumption, installed base, repair trends, product lifecycle status, and business inputs.
Added 9 mins ago
TH
Loss Prevention Specialist Full Time- 6 Month Contract (WHITBY NORTH)
The Home Depot Canada
Brooklin, ON
- Full-time
…concerns of all associates and remain focused on store specific business…
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TH
Loss Prevention Specialist Full Time
The Home Depot Canada
Toronto, ON · Etobicoke, ON
- Full-time
…concerns of all associates and remain focused on store specific business…
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Global Seeder Product Specialist
CNH
Saskatoon, SK
- Full-time
…customers to understand global market needs, gather competitive intelligence, and support business expansion through customer visits, focus groups, customer clinics, and related research…
Added 10 mins ago
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Loss Prevention Specialist Full Time
The Home Depot Canada
Mississauga, ON
- Full-time
…concerns of all associates and remain focused on store specific business…
Added 10 mins ago
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Client Advisor- EN
RBC
Quebec, QC
- Part-time
…individual needs. You will champion the RBC brand and drive business by supporting new client acquisition and deepening existing relationships. If you have the self-motivation to deliver…
Added 25 mins ago
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Community General Manager II, Imperial Service
CIBC
Burlington, ON
- Full-time
…solutions to meet our clients goals. As a Community General Manager (CGM), you will build a capable and motivated team through proactive talent management. You will be empowered to create a…
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Manager, Dynamics 365 F&O Consulting
BDO
Vancouver, BC · Hamilton, ON · Ottawa, ON · Toronto, ON
- Full-time
BDO Canada is seeking a Manager, Dynamics 365 F&O Consulting to join our fast-paced and growing Dynamics 365 F&O consulting practice, with the ability to work from anywhere in Canada. This…
Added 25 mins ago
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Pricing Analyst
Staples Inc.
Richmond Hill, ON
- Full-time
…support to the Sales, Pricing, and Merchandising teams to empower business leaders to make timely and well-informed pricing decisions. This will be accomplished using pricing and cost to…
Added 25 mins ago
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Business Manager, Retail Products
Manulife
Halifax, NS · Toronto, ON · Waterloo, ON · Montreal, QC
- Full-time
The Business Manager, Retail Products is a high-impact individual contributor responsible for driving operational excellence, enabling disciplined execution, and ensuring organizational…
Added 25 mins ago
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Assistant Maintenance Manager
JLL
Pitt Meadows, BC
- Full-time
The Assistant Maintenance Manager leverages leadership skills and technical knowledge to lead a team of maintenance mechanics, working in conjunction with robotics, and controls systems…
Added 25 mins ago
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Investment Attraction Manager
Strathcona County
Sherwood Park, AB
- Full-time
Guide the continued development and adoption of customer relationship management and digital business-support tools, including the Business Directory, Investment Intelligence Tool and…
Added 40 mins ago
SD
Merchandiser, Hourly Part Time Flexible Shifts Greenlight Requisition
Shoppers Drug Mart
Toronto, ON
- Part-time
Supports Front Store Manager/Assistant Front Store Manager in maintaining the quality and standards
Added 40 mins ago
SD
Assistant Front Store Manager, Hourly Full Time Flexible Shifts
Shoppers Drug Mart
Barrie, ON
- Full-time
To assist the Front Store Manager (FSM) in managing the human, physical and financial resources of the store and in ensuring that store objectives are achieved by focusing on improving…
Added 40 mins ago
SD
Assistant Front Store Manager, Hourly Full Time Flexible Shifts
Shoppers Drug Mart
Ottawa, ON
- Full-time
To assist the Front Store Manager (FSM) in managing the human, physical and financial resources of the store and in ensuring that store objectives are achieved by focusing on improving…
Added 40 mins ago
SD
Assistant Front Store Manager, Hourly Full Time Flexible Shifts Greenlight Requisition
Shoppers Drug Mart
Carleton Place, ON
- Full-time
To assist the Front Store Manager (FSM) in managing the human, physical and financial resources of the store and in ensuring that store objectives are achieved by focusing on improving…
Added 40 mins ago
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Summer Student - CRU Project Support
AltaLink
Calgary, AB
- Other
…This Summer Student – CRU Project Support will report to the Manager, Project Support CRU, and work closely with the project managers, functional teams, and management to ensure project…
Added 40 mins ago
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(CAN) Self Checkout Attendant
Walmart
Georgetown, ON
- Part-time
…and escalate cash or technical issues to the Customer Service…
Added 40 mins ago
LC
Épicerie Assistant Gérant/Superviseur temps partiel jour
Loblaw Companies Limited
Quebec, QC
- Part-time
Our commitment to Sustainability and Social Impact is an essential part of the way we do business, and we focus our attention on areas where we can have the greatest impact. Our approach to…
Added 40 mins ago
LC
PC Express Department Manager
Loblaw Companies Limited
Vancouver, BC
- Full-time
We’re looking for Talented Passionate Leaders with a proven record of delighting customers and growing sales. As a Manager in one of our stores, you will have an immediate impact on sales…
Added 40 mins ago
LC
Grocery Department Manager Nights
Loblaw Companies Limited
London, ON
- Full-time
Our commitment to Sustainability and Social Impact is an essential part of the way we do business, and we focus our attention on areas where we can have the greatest impact. Our approach to…
Added 40 mins ago
LC
Meat/Seafood Department Manager
Loblaw Companies Limited
Windsor, ON
- Full-time
Our commitment to Sustainability and Social Impact is an essential part of the way we do business, and we focus our attention on areas where we can have the greatest impact. Our approach to…
Added 40 mins ago
LC
Associate Product Manager, Enterprise Initiatives
Loblaw Companies Limited
Brampton, ON
- Full-time
Associate Product Manager, Enterprise Initiatives - 12mth Contract

SysAid

Sales Enablement Manager

Toronto, ON, Canada

Full-time

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Job details

Job type: Full-time
Apply by: Oct 26, 2027
Posting language: English
Posted: Oct 26, 2026

Original job description

SysAid is a high-growth SaaS company selling an IT Service Management Platform powered by AI. The ITSM space is experiencing rapid growth as businesses worldwide accelerate their digital transformation and adopt new technologies and workstyles. SysAid has been recognized in the Gartner Magic Quadrant for ITSM and was awarded the AWS Rising ISV Star Award for 2022.

We have over 4,000 customers in 140 countries. We are deployed in 42 languages and used daily by over 100,000 system administrators. Our software impacts the daily working lives of over 9 million end users.

The Role

This is not a traditional Sales Enablement seat. We are building an AI-first enablement engine, and this role is its architect and operator. You will define how a global sales and customer success organization learns, prepares and wins, then use Claude and MCP-connected systems to deliver that enablement at scale, rather than through manual training cycles and static content.

You will be the key driver in turning our go-to-market strategy into seller behavior and results in every region. You will report directly to the revenue leader and partner with Sales, Customer Success, Marketing, Product and Revenue Operations, so your work shapes how every seller prepares, engages and closes.

What You Will Own

Enablement Strategy & Sales Readiness
Own the global enablement strategy and roadmap, tied directly to revenue goals, and the readiness plan for every segment, role and region.
Define what great looks like at each stage of the seller journey, from onboarding and ramp through ongoing development and career path, and build the system that gets people there faster.
Lead launch readiness for new products, pricing and positioning, so the field is ready on day one rather than weeks later.
Partner with sales leaders to set the methodology, coaching cadence and standards that run through the organization.
AI-First Enablement Model
Design and own the model for what Claude and connected agents deliver across enablement, such as personalized onboarding, on-demand coaching, call review, deal-specific prep and content generation, and where human-led enablement adds the most value.
Turn Gong call data and Salesforce outcomes into continuous coaching signals, pinpointing the behaviors and messages that win and delivering them to reps at the point of need.
Build and govern AI-powered workflows for messaging, persona and account research, outreach and objection handling, using Clay, ZoomInfo and Lemlist, with consistent quality and brand control.
Set standards for prompts, agents and guardrails so AI output is accurate, on-message and trusted by the field.
Messaging & Content Strategy
Own the sales narrative and messaging architecture across the buyer journey, working with Marketing and Product to align it to customer needs and market position.
Run content as a living, AI-assisted system, with a single source of truth that is kept current, easy to find and measured for usage and impact, instead of a static repository.
Direct the strategy and storyline for major moments such as sales kick-off and quarterly sales meetings.
Enablement Performance & Revenue Impact
Define the KPIs for enablement, including ramp time, productivity, win rate, sales cycle, content effectiveness and adoption, and connect each program to revenue outcomes.
Use Snowflake, Salesforce and Gong data, with Revenue Operations, to find where performance gaps are and direct enablement to close them.
Report clearly to executive leadership on what is working, what is not and where to invest next.
Enablement Technology & Architecture
Own the enablement technology stack as one connected system (Claude, Salesforce, Gong, Snowflake, Lemlist, Clay, ZoomInfo, Juno and Accord) and the way it supports the seller workflow.
Evaluate and introduce new tools and AI capabilities, retire what no longer earns its place, and ensure sellers are trained and actually using what we invest in.

How You Will Work: AI-First:

Claude, connected through MCP to our core systems, is your primary team. You will be expected to:

Default to AI for content creation, material updates, training design, call analysis, research and reporting, and bring in people where judgment, coaching and relationships make the difference.
Build, test and improve agentic enablement workflows end to end, and measure accuracy, adoption and business results.
Treat every manual, repetitive enablement task as a candidate for automation, and have a clear point of view on what should always stay human.
Teach the global sales organization to work this way, through clear playbooks, live examples and visible wins.

Your Impact:

Be the force multiplier for a global sales organization selling across 140 countries, with enablement that reaches every rep, region and language.
Build SysAid's AI-first enablement program from the ground up, a completely reinvigorated approach with you as its architect.
Convert strategy into measurable results: faster ramp, higher win rates, shorter sales cycles and stronger seller confidence and retention.
Direct visibility and influence with executive leadership, with ownership of a scope that grows as the AI-first model scales.

Requirements:

5+ years in a high-performance B2B technology sales organization, in sales, enablement or learning and development, including at least 3 years as a direct-to-market quota-carrying individual contributor. SDR or BDR experience is a plus.
Demonstrated experience using AI and LLM tools such as Claude, agents or MCP-style integrations to build and automate real business workflows; a hands-on builder mentality.
Proven track record of designing, building and iterating a sales enablement program, with measurable results.
Deep understanding of sales processes, methodologies and best practices, and the credibility to coach and influence sellers and sales leaders.
Experience with a modern GTM stack (Salesforce, Gong and similar) and with content and learning management systems; analytical mindset, with comfort using data to drive decisions.
Excellent communication and presentation skills, with the ability to convey complex ideas clearly and concisely.
Based in, or willing to relocate to, Toronto: in office at Liberty Village four days per week.

What We Offer

Competitive compensation package
Medical, Vision, Dental, and RRSP
Life, AD&D, and LTD Insurance
Gender-neutral parental leave
Option plan from Day 1

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More about this job

Responsibilities

Own the global sales enablement strategy and build an AI-first enablement model using Claude and connected systems to support onboarding, coaching, content, and seller workflows. Measure enablement impact against revenue outcomes, manage the GTM technology stack, and align sales messaging and readiness across regions and teams.

Requirements

Requires at least five years in a high-performance B2B technology sales organization, including at least three years as a quota-carrying individual contributor, plus a proven record of building measurable sales enablement programs. Candidates should have hands-on experience with AI and LLM workflows, strong sales process and coaching expertise, familiarity with modern GTM tools and analytics, and be based in or willing to relocate to Toronto.

Skills

Sales Enablement
Sales Strategy
Sales Coaching
AI Workflow Automation
Claude and LLM Tools
Agentic Workflows
Salesforce
Gong
Snowflake
Sales Messaging
Content Strategy
Revenue Analytics
Sales Readiness
Go-to-Market Strategy
Communication and Presentation
Learning and Development

Benefits

Medical Insurance
Vision Insurance
Dental Insurance
RRSP
Life Insurance
Accidental Death and Dismemberment Insurance
Long-Term Disability Insurance
Gender-Neutral Parental Leave
Stock Options

Visa sponsorship

Not detected in the job text

Keywords

Sales Enablement
Artificial Intelligence
Claude
MCP
LLMs
Agentic Workflows
Salesforce
Gong
Snowflake
Lemlist
Clay
ZoomInfo
Juno
Accord
Revenue Operations
IT Service Management
SaaS
B2B Technology Sales
Sales Readiness
Sales Coaching
Sales Methodology
Go-to-Market Strategy
Sales Messaging
Content Management
Learning Management Systems
Revenue Analytics
Sales Performance Metrics
Product Launch Readiness
Account Research
Objection Handling

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