Find work in Canada.

497,267 jobs across our Canadian network. How we count

Jobs in Canada

25+ jobs

Email me new jobs Save this search

Added 4 mins ago
Customer Success Operations Analyst
Global Relay
Vancouver, BC
…expect from an established company, we are not your typical technology company. Global Relay is a career-building company. A place for big ideas. New challenges. Groundbreaking innovation.…
Added 4 mins ago
T
Talent Acquisition Coordinator
Trulioo
Remote, Canada
- $60,000 to $70,000 CAD / year
- Full-time
- Remote
…meets innovation and contribute to a world where trust and technology…
Added 4 mins ago
RI
Associate Product Manager
Remarcable, Inc.
Vancouver, BC
- $90,000 to $115,000 CAD / year
- Full-time
Lead agile ceremonies with engineering pods, including sprint planning, backlog prioritization, and retrospectives to ensure steady delivery.
Added 4 mins ago
RI
AI Engineer
Remarcable, Inc.
Remote, Canada
- Full-time
- Remote
Lead or support projects such as AI-assisted AP automation, a natural-language assistant for our customers, and AI-powered supplier onboarding.
Added 4 mins ago
RB
Senior Director, DevOps Product Management and Strategy
Royal Bank of Canada
Toronto, ON
- Full-time
You will lead the multi-year transformation of how RBC develops and delivers technology, focusing on AI-integrated SDLC frameworks, harness engineering practices, and developer productivity…
Added 4 mins ago
CC
Retail Shift Leader
Canna Cabana
Grande Prairie, AB · Prairie Mall, Grande Prairie, AB
- Part-time
Skills to monitor and lead by example as required
Added 19 mins ago
HS
CA Financial Controller
Henry Schein Canada
Surrey, BC
- Full-time
…combined with expert business coaching, to help connect dental technology so it works as one. When technology connects, more data is shared, more tasks are automated, and more work gets…
Added 19 mins ago
NM
Agriculture Equipment Technician
Nelson Motors and Equipment
Redvers, SK
- Full-time
We're looking for Agricultural Equipment Technicians who lead by example, support a strong team environment, and deliver service excellence that reflects our promise of reliable,…
Added 19 mins ago
WB
Head of Manufacturing, Plant Production
Waterloo Biofilter Systems Inc.
ON · Ontario, Canada
- $100,000 to $130,000 CAD / year
- Full-time
Lead the plant operations of a fast-growing Canadian manufacturer, with the freedom to overhaul production and reshape how the plant runs for years to come
Added 19 mins ago
KB
Project Sales Associate
Kent Building Supplies
Moncton, NB
- Full-time
…Limited, you are part of a dynamic team of professionals who lead with integrity and are passionate about delivering results. With a culture that nurtures talent and creates an inclusive…
Added 19 mins ago
KB
Cashier
Kent Building Supplies
Clarenville, NL
- Part-time
…Limited, you are part of a dynamic team of professionals who lead with integrity and are passionate about delivering results. With a culture that nurtures talent and creates an inclusive…
Added 19 mins ago
N
Director of AI Delivery
nesto
Toronto, ON
- Full-time
…end-to-end mortgage experience powered by best-in-class AI technology. Fast, simple, and fully digital, nesto has been recognized as CLA Lender of the Year for three consecutive years.…
Added 19 mins ago
E
Data Scientist
Ericsson
Ottawa, ON
- Full-time
Added 19 mins ago
B
Systems Analyst II
BGIS
Markham, ON
- Full-time
The System Analyst II will lead the management and maintenance of key data center and network infrastructure to ensure successful realization of operational targets. As someone who has…
Added 19 mins ago
H
Maintenance Team Lead
Hendrickson
Stratford, ON
- Full-time
…through the efficient management of available skill trades. Lead and support maintenance staff through the daily execution of their duties. Also gives technical direction and performs other…
Added 19 mins ago
EW
Project Manager
ERCO Worldwide
Saskatoon, SK
- Full-time
…scale. As one of the largest suppliers of Chlorine Dioxide technology in the world, we are devoted to building genuine customer relationships and delivering innovative, sustainable chemical…
Added 19 mins ago
EW
Senior Plant Process Engineer
ERCO Worldwide
Saskatoon, SK
- Full-time
…scale. As one of the largest suppliers of Chlorine Dioxide technology in the world, we are devoted to building genuine customer relationships and delivering innovative, sustainable chemical…
Added 19 mins ago
FC
Faculty Teaching and Learning Development Consultant
Fanshawe College
London, ON
- Full-time
Lead faculty teaching development for new full-time and non-full-time faculty, ensuring alignment with college teaching standards and teaching excellence
Added 19 mins ago
I
Senior Consultant- Life Insurance
Infosys
Toronto, ON
- Full-time
…transform and innovate. Our consultants are industry experts that lead complex change agendas driven by disruptive technology. With offices in 20 countries and backed by the power of the…
Added 19 mins ago
GR
Customer Success Operations Analyst
Global Relay
Vancouver, BC
- Full-time
…expect from an established company, we are not your typical technology company. Global Relay is a career-building company. A place for big ideas. New challenges. Groundbreaking innovation.…
Added 19 mins ago
CC
Branch Lead and Backup Driver - Permanent Full-Time - Port Coquitlam, BC
Chit Chats
Port Coquitlam, BC
- Full-time
We’re looking for a Branch Lead (with possibility of taking on a Driver role on-call) who brings positive energy, curiosity and care to everything they do.
Added 19 mins ago
N
Director of AI Delivery
nesto
Montreal, QC
- Full-time
…end-to-end mortgage experience powered by best-in-class AI technology. Fast, simple, and fully digital, nesto has been recognized as CLA Lender of the Year for three consecutive years.…
Added 19 mins ago
SP
Proposal Lead
Spark Power ⚡
AB · Edmonton, AB
- Full-time
…seeking to look for an experienced and results-driven Proposal Lead to lead the development and execution of winning pursuit strategies for utility, renewable energy, and industrial…
Added 19 mins ago
UI
Business Development Representative
Util-Assist Inc.
Newmarket, ON
- Full-time
…navigate digital transformation - empowering them with smart technology, data-driven solutions, and customer-first services. From outage communications to billing support and grid security,…
Added 19 mins ago
VB
Senior C++ Software Engineer - VxWorks
Vaco by Highspring
Toronto, ON · Greater Toronto Area, Canada
- $100,000 to $140,000 CAD / year
- Full-time
Lead designs for safety critical, real-time software solutions

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

Apply About employer

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

Report this job