Find work in Canada.

508,432 jobs across our Canadian network. How we count

Jobs in Canada

25+ jobs

Email me new jobs Save this search

Added 5 mins ago
CI
Senior Analyst, Procurement
CPP Investments | Investissements RPC
Toronto, ON
- Full-time
Working closely with the Manager and Associate, Procurement, you will enhance visibility into enterprise vendor relationships, support vendor performance management and translate complex…
Added 5 mins ago
B
QA Analyst
BMO
Toronto, ON · BMOPLACE
- Full-time
…payment processing, and customer communication workflows. Perform data validation and end-to-end testing within and across multiple integrated banking systems. Log, track, and verify…
Added 5 mins ago
AC
Specialist, Product Delivery - Temporary
Air Canada
Dorval, QC
- Full-time
Maintain delivery dashboards and governance artefacts using agreed tools and reliable source data.
Added 20 mins ago
TU
Academic and Student Programs Coordinator
The University of British Columbia
Kelowna, BC
- $5,519 to $6,326 CAD / month
- Full-time
The Academic & Student Programs Coordinator reports to the Manager, Administration and works closely with faculty members, academic leaders, students, and administrative colleagues across…
Added 20 mins ago
NG
Finance Manager
New Gold Inc.
Emo, ON
- Full-time
The Manager, Finance is a key member of the mine site leadership team responsible for the accounting, financial reporting, budgeting and forecasting, Life of Mine preparation, site payroll,…
Added 20 mins ago
CS
Manager, Supply Chain Operations and Analytics
Canadian Standards Association
Toronto, ON
- $100,890 to $132,416 CAD / year
- Full-time
The Manager, Supply Chain Operations and Analytics, is responsible for supporting procurement operations through data analysis, reporting, supplier governance, travel and expense program…
Added 20 mins ago
SI
AI Product Owner
Supra ITS
Mississauga, ON
- Full-time
…and deploy agents; end users work with them over documents, data, policy and operational…
Added 20 mins ago
R
Senior Manager, Operational Risk / IT Risk and Compliance
RBC
Toronto, ON
- Full-time
Senior Manager Operational Risk / IT Risk and Compliance is responsible for supporting the management of Operational Risk and Technology / Cyber Risk supporting the broader Payments…
Added 20 mins ago
SA
Manager, Procurement Sr
Standard Aero
Winnipeg, MB
- Full-time
As a Senior Manager, Procurement you’ll be responsible for leading strategic sourcing and procurement activities that support StandardAero’s global MRO operations. This role drives supplier…
Added 20 mins ago
O
Data & Analytics Manager
OLG
Sault Ste. Marie, ON · Toronto, ON · York Mills Office
- Full-time
…to lead business-aligned analytics delivery, enablement, and data product development within an assigned portfolio by translating stakeholder priorities into trusted analytics, reporting,…
Added 20 mins ago
T
Data Scientist III
TD
Toronto, ON
- Full-time
We are seeking a Data Scientist III to lead AI adoption and AI-enabled process transformation for the CPSB AI2 team. This role will work across business, analytics, data, technology, risk,…
Added 20 mins ago
NC
Business Analyst – Technology Training
NAV CANADA
Ottawa, ON
- Full-time
The Business Analyst - Technology Training supports the planning, coordination, analysis, governance, and continuous improvement of technology training programs, products, and services.…
Added 35 mins ago
MU
Project Manager, Harmonization
McGill University
Victoria, BC · James Admin. Bldg.
- Full-time
Reporting to the Vice-President, Communications and Institutional Relations (CIR) and Executive Sponsor, the Project Manager, Harmonization leads the planning, oversight, and execution of a…
Added 35 mins ago
C
Senior Financial Analyst
Campbell's
Mississauga, ON · CAN - ON - Mississauga
- Full-time
…with Customer, Sales and Brand teams. Under the guidance of Manager, FP&A, this role supports profitability analysis, forecasting, annual and strategic plans, innovation business cases,…
Added 35 mins ago
B
Sr. Applied AI Scientist – Generative AI & Agentic Systems
BMO
Toronto, ON · FCP
- Full-time
…solutions while helping shape industry-leading practices for the governance of Generative AI and Agentic AI systems in a highly regulated…
Added 50 mins ago
KC
Senior Manager - IT ICFR
KPMG Canada
Ottawa, ON
- Full-time
Our Technology Risk Consulting services team is growing and we are looking for Senior Manager to join our team in Toronto. The Technology Risk Consulting practice provides a variety of…
Added 50 mins ago
A
Security GRC Specialist
Aviso
Toronto, ON
- $105,000 to $125,000 CAD / year
- Full-time
Reporting to the Director of Security Governance, Risk & Compliance (GRC), the Security GRC Specialist will be responsible to govern the risk management lifecycle, including monitoring…
Added 50 mins ago
Manager, GCEC & VA SSI Supervision
Scotiabank
Toronto, ON
Strong understanding of GCEC and Virtual Advice operations, risk management practices, business controls, compliance governance and change management.
Added 50 mins ago
R
Operations Strategy, Sr Manager/Gestionnaire principal, stratégie des opérations
RTX
Longueuil, QC
- Full-time
Added 50 mins ago
E
Senior Portfolio & Program Manager, Operational Technology & Engineering
Equinix
Toronto, ON
- Full-time
The Senior Portfolio & Program Manager, Operational Technology & Engineering is responsible for the integrated portfolio of Operational Technology & Engineering (OT&E) initiatives across…
Added 1 hour ago
KS
Engineering Manager - Industrial Automation & Power Systems
Kinetic Search Group
Vancouver, BC · Greater Vancouver Metropolitan Area
- $170,000 to $190,000 CAD / year
- Full-time
We are seeking an accomplished Engineering Manager to lead and further develop a multidisciplinary engineering team specializing in electrical power systems, industrial automation, and…
Added 1 hour ago
T
Security Manager
TERAGO
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Protect proprietary code, customer and network data, and personal information through data loss prevention, tenant and data isolation, least privilege, and insider-risk controls.
Added 1 hour ago
D
Senior Revenue Operations Manager (Remote Canada)
Directive
Remote, Canada
- Full-time
- Remote
…measurable growth for B2B SaaS and tech companies. We believe in data-backed strategy, radical accountability, and world-class execution across every channel - Paid Media, SEO & Content,…
Added 1 hour ago
D
Senior Marketing Operations Manager (Remote Canada)
Directive
Remote, Canada
- Full-time
- Remote
…measurable growth for B2B SaaS and tech companies. We believe in data-backed strategy, radical accountability, and world-class execution across every channel - Paid Media, SEO & Content,…
Added 1 hour ago
1
Senior GTM Program Manager
1Password
Remote, Canada
- Full-time
- Remote
…trusted. We innovated the market-leading enterprise password manager and pioneered Unified Access Management, a new cybersecurity category built for the way people and AI agents work today.…

SysAid

Manager, Sales Enablement

Toronto, ON, Canada

Full-time

Apply About employer

Applications open in a new tab.

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

Apply About employer

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

Report this job