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Added 36 mins ago
TC
Winter Equipment Operator II Casual
The Corporation of UCLG
ON · Greenbush, ON
- Part-time
Training: Our Public Works division offers paid training: One-Person Snow Plow Operator and we cover the cost of PPE.
Added 51 mins ago
C
CNC Machine Operator - Precision Equipment
CyberCoders
Chatham, NB
- $30 to $32 CAD / hour
- Contract
A well-established global manufacturer is seeking a CNC Machine Operator to join its growing team in Blenheim, Ontario. This is an excellent opportunity for a machinist who enjoys working…
Added 51 mins ago
HR
Senior Software Engineer – Drone Control & Simulation (Defense and Dual-Use)
Haply Robotics
Montreal, QC
- Full-time
The job has two pillars. Drone control: how the operator flies the drone, from direct control to assisted modes. The simulation environment: where operators train, and where the team tests…
Added 1 hour ago
PC
Retail Inventory Specialist
Pursuit Collection
Canmore, AB · CAN - Canmore Office (Operations)
- Full-time
…here to embrace the extraordinary. To watch the sunrise and set each day in a place that, for many people, exists only in their imagination. To build career experience beside seasoned…
Added 1 hour ago
J
Senior Vice President, Capital Markets, Investments & Project Finance - DG Solar Company
J&T
Toronto, ON
- Full-time
Our client is a fast-growing developer, owner and operator of community solar, distributed generation and energy storage assets in the US. They are hiring a Senior Vice President to lead…
Added 1 hour ago
WI
CNC Turret Punch Press Operator
Wesgar Inc.
Port Coquitlam, BC
- $22 to $25 CAD / hour
- Full-time
We are looking for an experienced CNC Turret Punch Press Operator to join our production team on the graveyard shift.
Added 1 hour ago
MH
Production Supervisor 1st Shift
MAT Holdings, Inc.
Ingersoll, ON
- Full-time
Performs set-up operations for all part numbers and verifies quality by dimensional and process material testing.
Added 2 hours ago
TP
Specialist, Airport Bussing (Term Opportunity - One Year)
Toronto Pearson International Airport
Toronto, ON
- Temporary
A “DA” class Airside Vehicle Operator’s Permit (AVOP) or successfully obtain one within thirty (30) days of appointment to the position.
Added 2 hours ago
C
CNC Machine Operator - Precision Equipment
CyberCoders
Chatham, NB
- $30 to $32 CAD / hour
- Contract
A well-established global manufacturer is seeking a CNC Machine Operator to join its growing team in Blenheim, Ontario. This is an excellent opportunity for a machinist who enjoys working…
Added 2 hours ago
IC
Head of YouTube (Strategy, Scripting & Team Lead)
Impact Clients
Remote, Canada
- $75,000 to $150,000 USD / year
- Full-time
- Remote
…You'll work directly with Richard and the leadership team to set direction, goals and KPI's and lead, hire and manage a creative team…
Added 2 hours ago
1
Snow Removal Equipment Operator
12571555-b10d-4781-ae01-09366cea0dab
Hamilton, ON
- $25 to $35 CAD / hour
- Temporary
Provide traffic control, including the set up and take down of traffic control signs
Added 3 hours ago
CW
Process Operator (Day Shift)
CG Wellington
ON · Arthur, Ontario
- Full-time
Set up equipment and stage materials for production runs
Added 4 hours ago
S
Manual Lathe Operator (Brampton)
Savaria
Toronto, ON · Greater Toronto Area, Canada
- $26 to $30 CAD / hour
- Full-time
We are seeking a skilled CNC and Manual Lathe Operator to join our manufacturing team. The successful candidate will be responsible for operating, setting up, and maintaining both manual…
Added 4 hours ago
MH
Service Manager
Minor Hotels
Ottawa, ON
- Full-time
Minor Food is one of Asia's most dynamic food service companies and a leading global restaurant operator, with more than 2,700 outlets across 25 countries. Our portfolio spans a wide range…
Added 4 hours ago
MK
Equipment Operator I
Michael Kors
Montreal, QC
- Full-time
The Equipment Operator II reports to the Distribution Center Outbound Processing Lead. This member of the Distribution Center team operates lift equipment and performs various general…
Added 4 hours ago
MK
Equipment Operator I
Michael Kors
Montreal, QC
- Full-time
The Equipment Operator II reports to the Distribution Center Outbound Processing Lead. This member of the Distribution Center team operates lift equipment and performs various general…
Added 4 hours ago
HR
Senior Software Engineer – Haptic Control for Defense and Dual-Use Drones and Vehicles (Rust)
Haply Robotics
Montreal, QC
- Full-time
…that connects a Haply controller to a vehicle. It sends the operator’s hand movements to the vehicle and turns what the vehicle senses into forces the operator feels. It runs both in…
Added 5 hours ago
WC
Building Operator (2026-400-HHS)
WoodGreen Community Services
Toronto, ON
- Full-time
…and buildings owned and/or managed by WoodGreen. The building operator shall perform their duties in a professional manner and operate within the schedules and directions set out by…
Added 6 hours ago
GT
Specialist, Airport Bussing (Term Opportunity - One Year)
Greater Toronto Airports Authority
Toronto, ON
- Full-time
A “DA” class Airside Vehicle Operator’s Permit (AVOP) or successfully obtain one within thirty (30) days of appointment to the position.
Added 6 hours ago
VA
Opérateur de production/ Production Operator
Vetio Animal Health
Quebec, QC · Ville St Laurent, Quebec
- Full-time
Set up, start-up, monitor, and shut down equipment; adjust process parameters (speed, spray rate, temperature, end-point moisture) to meet specifications.
Added 6 hours ago
WC
Building Operator (2026-400-HHS)
WoodGreen Community Services
Toronto, ON
- Full-time
…and buildings owned and/or managed by WoodGreen. The building operator shall perform their duties in a professional manner and operate within the schedules and directions set out by…
Added 6 hours ago
C
CNC Machine Operator - Precision Equipment
CyberCoders
Chatham, NB
- $30 to $32 CAD / hour
- Contract
A well-established global manufacturer is seeking a CNC Machine Operator to join its growing team in Blenheim, Ontario. This is an excellent opportunity for a machinist who enjoys working…
Added 7 hours ago
S
Manager, Sales Enablement
SysAid
Toronto, ON
- Full-time
…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…
Added 7 hours ago
MT
CNC Setup Technician
Modern Technical Staffing Inc.
Guelph, ON
- Full-time
Set up, operate, and optimize 4 & 5-axis CNC milling machines, ensuring efficient production, quality output, and adherence to tight tolerances.
Added 7 hours ago
K
Processing Operator 1 - Night Shift - Fixed term 12 months
Kenvue
Guelph, ON
- Full-time
Successfully execute all manufacturing steps associated with cleaning/sanitation, set-up and manufacturing operations associated with the work center the operator has been assigned to.

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

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