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Added 9 mins ago
GG
Regional Sales Manager - Canada Central & East
Gallagher Group
NB · St. John's, NL · NL · NS · ON · PE · Quebec, QC · New Brunswick, Canada · Newfoundland & Labrador, Canada · Nova Scotia, Canada · Ontario, Canada · Prince Edward Island, Canada
- Full-time
As Regional Sales Manager, you'll play a key role in driving the growth of Gallagher Security across two Canadian territories:
Added 9 mins ago
SD
Assistant Front Store Manager, Hourly Full Time Flexible Shifts Greenlight Requisition
Shoppers Drug Mart
Halifax, NS
- 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 9 mins ago
D
HR Advisor / Conseiller(ère) en ressources humaines
DWF
Toronto, ON
- Full-time
DWF takes pride in cultivating a collegial workplace that promotes teamwork, professional development, and social connection among staff and lawyers alike. We believe people thrive when…
Added 9 mins ago
W
(CAN) GM Lead Department Manager
Walmart
Camrose, AB
- Full-time
…partnership with the General Merchandise and Fashion Assistant Manager and ensure a high level of customer service and while ensuring task…
Added 9 mins ago
Clinician, Wound and Skin Care
Fraser Health
BC · Fraser Health, British Columbia
…practice and recommending changes to existing standards to the…
Added 9 mins ago
Licensed Practical Nurse Educator, Long Term Care
Fraser Health
BC · Hope / Agassiz / Harrison Hot Springs / Kent, British Columbia
Determines education priorities that meet learner needs, in collaboration with the Manager, Team Leader, Resident Care Coordinator, Clinical Nurse Educator and Clinical Resources Nurse as…
Added 9 mins ago
Nurse Clinician, Skin & Wound Care
Fraser Health
Chilliwack, BC
…clinical practice, recommends changes to existing standards to the Manager, and participates on regional and provincial committees related to skin and wound care…
Added 9 mins ago
FH
Patient Care Coordinator
Fraser Health
Abbotsford, BC
- Part-time
Identifies learning requirements of staff and, in conjunction with the Manager, Educator and other members of the clinical team, provides input into the development of learning objectives;…
Added 9 mins ago
FH
Registered Nurse, Emergency - Specialty Qualified
Fraser Health
Chilliwack, BC
- Part-time
Participates on nursing committees, care conferences and councils as assigned or as agreed to with the Manager.
Added 9 mins ago
TC
IT Service Desk Analyst
The Citco Group Limited
Toronto, ON
- Full-time
A career at Citco isn’t just a job – it’s an opportunity to excel in an environment that genuinely supports your personal and professional development.
Added 9 mins ago
Events Specialist
Canadian Mental Health Association BC Division
Vancouver, BC
…and the Bottom Line Conference in October. Reporting to the Manager, Development and Partnerships, the role carries out established event plans, timelines and budgets, and coordinates the…
Added 9 mins ago
EG
Event Producer - Hybrid (Project-Based)
Encore Global
Brampton, ON
- Full-time
…work collaboratively to find creative solutions during the development of projects. The Event Producer will ensure that all the right steps/process are followed and that the results of the…
Added 9 mins ago
EG
Event Operations Manager- Edmonton Convention Center
Encore Global
Edmonton, AB
- Full-time
…customer service, staff leadership, performance management, and development. Achieves the overall goals of the organization through effective workforce and inventory cost control. This…
Added 24 mins ago
PE
Administrative Assistant
PTW Energy Services
Hinton, AB
- Full-time
Preparing routine correspondence as directed by the Business Unit Manager.
Added 24 mins ago
OH
Senior Business Partner, Health Workforce Capacity
Ontario Health | Santé Ontario
Toronto, ON
- Full-time
Ongoing learning and career development opportunities designed to help you grow, advance, and thrive in your profession
Added 24 mins ago
TC
Permanent Open Position -FI-Gr 05 - 50% (PM)
Toronto Catholic District School Board
ON · York, ON
- Full-time
…an inclusive Catholic learning community that nurtures faith development and academic excellence through the love of God, neighbor, and…
Added 24 mins ago
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Operator II - Building Maintenance
City of Fort Saskatchewan
Fort Saskatchewan, AB
- Full-time
Training/education and professional development opportunities
Added 24 mins ago
AU
Security Guard - Various Casual Shifts
Allied Universal
Windsor, ON
- $18 CAD / hour
- Part-time
Undertake site specific training, follow direction and guidance from Site Supervisor or Manager
Added 24 mins ago
K
Scheduling Manager
Kiewit
Toronto, ON
- Full-time
As a Scheduling Manager, you’ll play a key role in the development and maintenance of project schedules utilizing company/district standards and scheduling techniques. This hands-on role…
Added 24 mins ago
CH
Radio Duty Attendant, CMH Revelstoke
CMH Heli-Skiing & Summer Adventures
BC · British Columbia, Canada
- Full-time
An opportunity to grow and learn in a work environment that promotes feedback and development.
Added 24 mins ago
E
Management Trainee
Enterprise
Antigonish, NS
- Full-time
Whether you see yourself in sales, business development, customer service, retail management, or operations, as a manager in training, you can count on a career path with a clear beginning…
Added 24 mins ago
CH
Assistant Lodge Manager, Monashees
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BC · British Columbia, Canada
- Full-time
An opportunity to grow and learn in a work environment that promotes feedback and development.
Added 24 mins ago
G
Regional Sales Manager - Canada Central & East
Gallagher
NL · New Chelsea, NL
- Full-time
As Regional Sales Manager, you'll play a key role in driving the growth of Gallagher Security across two Canadian territories:
Added 24 mins ago
WC
(CAN) Customer Service Manager
Walmart Canada
Drayton Valley, AB
- $15 CAD / hour
- Full-time
Position Summary...Working as a Customer Service Manager at Walmart Canada is a great opportunity to build strong leadership and operational skills in a fast paced retail environment. In…
Added 24 mins ago
G
Regional Sales Manager - Canada Central & East
Gallagher
St. John's, NL
- Full-time
As Regional Sales Manager, you'll play a key role in driving the growth of Gallagher Security across two Canadian territories:

SysAid

Sales Enablement Manager

Toronto, ON, Canada

Full-time

Apply About employer

Applications open in a new tab.

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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