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Assistant Manager
Cineplex
Calgary, AB · CPX Crowfoot Crossing
- Part-time
Forecast, initiate action/projects to drive the business forward and strengthen Cineplex Entertainment as Canada’s #1 premier film exhibition company.
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Senior Procurement Analyst
Canadian Tire Corporation
Toronto, ON
- Full-time
…execution of savings opportunities for a targeted portfolio of business…
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Customer Service Representative
BMO
Toronto, ON
- Part-time
…deliver the desired customer experience and achieve overall business…
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Credit Analyst, Commercial Banking
BMO
Vancouver, BC · FBT
- Full-time
Underwriting of new business transactions & annual reviews
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Manager, Salesforce Innovation & Enablement
BMO
Toronto, ON · BMOPLACE
- Full-time
The Manager, Salesforce Innovation & Enablement is required to maintain and manage core responsibilities related to all salesforce innovations to support business growth including marketing…
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Investment Support Officer
Scotiabank
ON · Mississauga, ON
…initiatives are executed / delivered in support of the team’s business strategies and objectives. Ensures all activities conducted are in compliance with governing regulations, internal…
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Officer Mortgage Operations
Scotiabank
Perth East, ON · Mississauga, ON
…initiatives are executed / delivered in support of the team’s business strategies and objectives. Ensures all activities conducted are in compliance with governing regulations, internal…
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Business Controls Officer
Scotiabank
Montreal, QC
As a Business Controls Officer you contribute to the success of Regulatory Controls and the Canadian Branch Network by conducting independent and rigorous reviews to support Global…
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Gestionnaire de Contrats de vente / Sales Contracts Manager
Airbus
Mirabel, QC · Montreal, QC
- Full-time
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Project Manager - Hybrid Power & Electrification
Hatch
Vancouver, BC
Hatch is seeking a Senior Project Manager to join our Power Business Unit and lead the delivery of utility, hybrid power, and electrification projects.
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Strategic Partnership Manager
Manulife
Halifax, NS · Toronto, ON · Waterloo, ON · Montreal, QC
- Full-time
As a Strategic Partnership Manager, you will play a critical role in leading initiatives, driving high value vendor relationships, optimizing third-party performance, and enabling strong…
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Senior Product Manager
Litera
Toronto, ON · Canada-Toronto, ON-Office
- Full-time
As a Senior Product Manager, you’ll own the vision, strategy, and roadmap for Litera’s Firm Intelligence Platform - the foundational layer that turns the data flowing through a law firm’s…
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Operating Practices Specialist
Metrolinx
Canada
- Full-time
…examinations and provide analysis and procedures to support ongoing business needs. They will also be responsible for the production and delivery of briefing materials to the Senior Manager…
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Lease Accountant (Contract)
LCBO
Toronto, ON
- Full-time
Reporting to the Senior Manager, Real Estate Administration & Analysis, the Lease Accountant is responsible for the accurate accounting, reporting, and financial administration of the LCBO…
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Solution Engineering Manager
Hitachi
Toronto, ON · (RSBU) Toronto
- Full-time
The Solution Engineering Manager (SEM) is the Technical Bid / Project manager for the Engineering organization. They provide the principle engineering delivery leadership, direction,…
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Amazon Brand Manager
Hadley Designs
Remote, Canada
- Full-time
- Remote
Own Your Catalog Like a Business, and Win on Amazon.
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Human Resources Business Partner
The Canada Life Assurance Company
Winnipeg, MB · London, ON · Toronto, ON · Montreal, QC
A hands-on project manager with a business partner mindset who has the experience and confidence necessary to work with senior business leaders, HR leaders, and employees at all levels to…
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Coordinator, Government Affairs
Independent Electricity System Operator
Canada
…IESO's engagement with government stakeholders. Reporting to the Manager, Government Affairs, you will work with senior leaders and government officials to advance the IESO's business and…
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Energy Group Leader
Mott MacDonald
Calgary, AB
…safety, quality, ethics, and compliance; and support sustainable business growth. Success will be assessed through measurable organisational outcomes, including resource performance,…
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Electrical Engineering Specialist I
Schneider Electric
AB · Edmonton, Alberta
- Full-time
…regarding the pay range can be directed to the recruiting / hiring…
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Senior Project Manager
Symbiotic Digital
Toronto, ON · Queen's Park Ontario Provincial Government, Ontario
- Contract
We are seeking an experienced Senior Project Manager to lead
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Senior Software Developer - ETL
Symbiotic Digital
ON · Downtown Toronto (Central Bay Street), Ontario
- Contract
pre-conversion and post-conversion support to business stakeholders.
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QA Training Specialist
Gilead Sciences
AB · CA - AB - Edmonton
- Full-time
Reporting to Sr. Manager, Quality Systems Training this role supports the development, delivery, and continuous improvement of learning and training programs across Quality and Operations.…
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Marketing Manager, Global Marketing, Consulting (24 Month Secondment/Fixed Term Contract)
KPMG
ON · Toronto, Ontario
- Full-time
…challenges. Here, you can build momentum that reaches beyond our business, develop skills for the future, and take ownership of your career with support at every stage. Join a firm where…
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Network Analyst
City of Leduc
Prince George, BC · Civic Centre
- Full-time
Reporting to the Manager, Vendor & Service Delivery, the Network Analyst is responsible for planning, implementing, maintaining, and optimizing the City's network and infrastructure…

SysAid

Manager, Sales Enablement

Toronto, ON, Canada

Full-time

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Job details

Job type: Full-time
Apply by: Nov 26, 2026
Posting language: English
Posted: Oct 27, 2026

Original job description

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, readiness programs, messaging, content, and technology stack, building an AI-first model that uses connected agents and systems to support seller workflows. Measure enablement performance against revenue outcomes, use data to identify gaps, and report results and investment priorities to executive leadership.

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 demonstrated success 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 content or learning systems, and be based in or willing to relocate to Toronto.

Skills

Sales Enablement
Enablement Strategy
Sales Readiness
AI Workflow Automation
Claude and LLM Tools
Sales Coaching
Sales Methodologies
Messaging Strategy
Content Strategy
Revenue Analytics
Salesforce
Gong
Snowflake
Prompt and Agent Governance
Change Management
Communication and Presentation

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
B2B Technology
SaaS
IT Service Management
Artificial Intelligence
Claude
MCP
AI Agents
Salesforce
Gong
Snowflake
Lemlist
Clay
ZoomInfo
Juno
Accord
Revenue Operations
Sales Readiness
Sales Coaching
Sales Methodology
Go-to-Market Strategy
Content Management
Learning Management Systems
Sales Kickoff
Ramp Time
Win Rate
Sales Cycle
Prompt Engineering
Workflow Automation
Performance Analytics

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