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Added 4 mins ago
BF
Senior Manager, Digital and Customer Applications
BC Ferries
BC · British Columbia, Canada
- Full-time
As Senior Manager, Digital and Customer Applications, you'll lead the teams and technology behind these experiences, ensuring our customer-facing applications are reliable, secure, and…
Added 4 mins ago
D-
Production Associate
DLF - BV
Surrey, BC
- Full-time
The Production Associate is responsible for supporting warehouse and production operations by performing a variety of tasks that ensure production goals are met efficiently, safely, and…
Added 4 mins ago
K
Marketing Manager
Kiocafe
Toronto, ON
- Full-time
…integrated beverage solutions that help businesses streamline operations, reduce labor requirements, and provide convenient, high-quality beverage…
Added 4 mins ago
JE
Automation Systems Designer - Mechanical
Johnson Electric
Ancaster, ON · Canada Ancaster - Automation Group Canada (General)
- Full-time
…vary in scope from simple material handling, fully automated product inspection cells, to complete pump assembly lines. Knowledge of a full range of motion methods (electrical, pneumatic)…
Added 19 mins ago
SH
Assistant Food & Beverage Manager | Full-time | Constantine
Silver Hotel Group
Toronto, ON
- Full-time
We’re looking for an Assistant Food & Beverage Manager who is ready to who is ready to roll up their sleeves, lead with heart, and help us build something exceptional
Added 19 mins ago
ET
Manager Marketing & Communications
E2IP TECHNOLOGIES
Montreal, QC
- Full-time
The Manager, Marketing & Communications leads E2IP's marketing team and owns how the company presents itself to customers and employees. The role sets the marketing roadmap, leads the…
Added 19 mins ago
WC
Full Time Staff Pharmacist - Courtenay - Campbell River
Walmart Canada
Courtenay, BC
- Full-time
Position Summary...The Staff Pharmacist assists the Pharmacy Manager in all aspects of the Pharmacy Operations. Provides patient care specific to each patient based on feedback received…
Added 19 mins ago
RH
Ecommerce Manager
Robert Half
Oshawa, ON
- Full-time
Oversee day-to-day eCommerce operations, website performance, digital merchandising, promotional campaigns, and product launches.
Added 19 mins ago
WC
(CAN) Health and Beauty Team Associate
Walmart Canada
Truro, NS
- Full-time
Position Summary...To provide exceptional customer service and assist in salesfloor operations in the Cosmetics department to ensure a positive shopping experience and drive customer…
Added 19 mins ago
AC
Financial Services Consultant
Assiniboine Credit Union
Rivers, MB
- Full-time
Reporting to the Branch Manager, the Financial Consultant plays a key role in deepening member relationships by delivering proactive, personalized advice and supporting a broad range of…
Added 19 mins ago
WC
Full Time Relief Pharmacist - Vancouver Island
Walmart Canada
Nanaimo, BC
- Full-time
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Added 19 mins ago
LN
Corporate Mechanical Maintenance Specialist
Logic NDT Solutions
Calgary, AB
- Full-time
The Corporate Mechanical Maintenance Specialist functions as a portfolio-wide Reliability and Asset Manager, shifting our multi-entity operations from reactive repairs to proactive asset…
Added 19 mins ago
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(CAN) Front End Checkout Team Associate
Walmart Canada
Brampton, ON
- Contract
Promotes company sponsor programs, ie. Credit card service, product protection and charity initiatives.
Added 19 mins ago
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Manager, Data Analytics and Reporting
Alexion Pharmaceuticals, Inc.
Mississauga, ON
- Full-time
The Manager, Analytics & Reporting will lead the creation of trusted, scalable analytics and reporting that power the US Commercial business across Specialty Pharmacy, Specialty Infusion…
Added 19 mins ago
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Senior Manager, Program Management
Walmart Canada
Mississauga, ON
- Full-time
A key responsibility is driving cross-functional accountability for identified opportunities. The Senior Manager will work with Operations, Product, Technology, eComm, Supply Chain, and…
Added 19 mins ago
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Shopper Marketing Manager
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Vancouver, BC
- Full-time
Our client is seeking a strategic and results-oriented Shopper Marketing Manager to lead the development and execution of shopper marketing, retail activation, and channel marketing…
Added 19 mins ago
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Relief Pharmacist
Walmart Canada
Waterloo, ON
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Research & Development Manager
TalentSphere Staffing Solutions
Niagara Falls, ON
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Collaborate with marketing and operations on product positioning
Added 19 mins ago
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Product Marketing Agent – Glass Hardware & Glazing
Quincaillerie Richelieu Ltée/Richelieu Hardware Ltd
Montreal, QC
- Full-time
We are currently looking for a Product Marketing Agent to join our team. The product marketing agent will report to the Product Manager and will assist him in the management of product…
Added 19 mins ago
WC
(CAN) Self Checkout Attendant
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Ancaster, ON
- Full-time
…opportunity to build valuable skills in customer service and retail operations. The Self‑Checkout Attendant supports a positive shopping experience by providing friendly, helpful service…
Added 19 mins ago
GN
Guest Experience Associate
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- Full-time
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Added 19 mins ago
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Garage Door Installer Helper
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Added 19 mins ago
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Free People Product Flow Manager
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Added 19 mins ago
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Senior Manager, Food Innovation Technology
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The Senior Food Innovation Technology Manager is the heart of our business and can balance the art and science of innovation, development, and food safety. They have passion for food and…
Added 34 mins ago
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Assistant Manager, Wealth Sales Support
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St. Catharines, ON · Toronto, ON · Etobicoke, ON
- Full-time
The role: Reporting to the Manager, Wealth Sales Support, the Assistant Manager, Wealth Sales Support leads the Mutual Fund Support Representatives who provide day-to-day operational and…

SysAid

Manager, Sales Enablement

Toronto, ON, Canada

Full-time

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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

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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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