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Added 10 mins ago
BO
Associate, Corporate and Commercial Banking Services
Bank of China (Canada)
Toronto, ON
- Full-time
The successful candidate will work closely with Relationship Managers and internal stakeholders across KYC, Operations, Credit Management, Compliance, and Product teams to facilitate timely…
Added 10 mins ago
BG
Foreman Service_CA
Brandt Group of Companies
Rocky View No 44, AB · Rocky View County, AB
- Full-time
Support service leadership by stepping into the Service Manager role during absences to ensure continuity of operations.
Added 10 mins ago
BG
Foreman
Brandt Group of Companies
Rocky View No 44, AB · Rocky View County, AB
- Full-time
…Optimization standards. The individual acts as the Service Manager when the Manager is away from the dealership and provide quotes and estimates to customers as required, review work orders…
Added 10 mins ago
PC
Team Leader - Hazardous Materials Division
Pinchin Canada
Richmond, BC
- $90,000 to $105,000 CAD / year
- Full-time
Reporting to the Operations Manager, the Team Leader is responsible for the efficient and profitable operation of their division within their assigned region. Team Leaders also fulfill a…
Added 10 mins ago
BG
Senior Project Manager
Brandt Group of Companies
Zehner
- Full-time
Brandt Development Ltd is currently seeking a Senior Project Manager for our Regina,SK, location.
Added 10 mins ago
BG
Territory Manager - Underground
Brandt Group of Companies
Milton, ON
- Full-time
The Territory Manager – Ditch Witch specializing in Underground and Tree Care is responsible for selling new and used equipment such as Ditch Witch and Morbark, within an assigned Area of…
Added 10 mins ago
BG
Territory Manager - Compact Construction Equipment
Brandt Group of Companies
Thunder Bay, ON
- Full-time
Brandt Tractor Ltd. is currently seeking a Territory Manager - Compact Construction Equipment for our Thunder Bay Construction & Forestry location
Added 10 mins ago
BH
Property Representative 1 - Distribution Acquisitions
BC Hydro
Vancouver, BC
- Full-time
…collaboratively with various business groups (Distribution/Field Operations, Engineering and Generation) as well as external stakeholders to support project delivery of distribution…
Added 10 mins ago
PL
Engineering Study Manager - PL#44559
Peter Lucas
Kamloops, BC
- Full-time
Peter Lucas Project Management invests in people and community to provide gold standard project delivery. We are currently looking for an Engineering Study Manager to join our team.
Added 10 mins ago
Branch Administrator
City of Edmonton
AB
Operating as the central information hub for the Office of the Branch Manager, you will deliver senior-level administrative support to ensure the efficiency and responsiveness of branch…
Added 10 mins ago
D
Senior Revenue Operations Manager (Remote Canada)
Directive
Remote, Canada
- Full-time
- Remote
We're hiring a Senior Revenue Operations Manager to own the systems our go-to-market runs on. You'll sit on the internal marketing team as the operator behind the Marketing and Sales teams,…
Added 10 mins ago
D
Senior Marketing Operations Manager (Remote Canada)
Directive
Remote, Canada
- Full-time
- Remote
We're hiring a Senior Marketing Operations Manager to own the systems our go-to-market runs on. You'll sit on the internal marketing team as the operator behind the Marketing and Sales…
Added 10 mins 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.…
Added 10 mins ago
UH
Program Services Manager, Spinal Cord Rehab - Inpatient Unit 2B & Outpatient Clinic
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- Full-time
The Program Services Manager, Spinal Cord Rehabilitation (Inpatient Unit 2B & Outpatient Clinic) provides strategic, operational, and clinical leadership for a multidisciplinary team within…
Added 10 mins ago
AG
Senior Mill Projects Engineer
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…within delegated authority and provide recommendations to the Manager - Processing for material changes.• Maintain project risk registers and actively manage technical, safety,…
Added 10 mins ago
SD
Post Office Manager, Hourly Full Time Flexible Shifts
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Toronto, ON
- Full-time
Leads by example and ensures that Post Office staff demonstrate our CORE Values
Added 10 mins ago
AY
Client Services Coordinator (CAN)
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AB · Edmonton, AB
- Full-time
Located in our Edmonton office and reporting to the Managing Director and Operations Manager, this role includes daily real estate administrative support in a fast-paced environment. As a…
Added 10 mins ago
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Front Office Manager
AccorHotel
Toronto, ON
- Full-time
Seeking a dynamically motivated, multi-tasked individual for the position of Front Office Manager. Candidates should be goal oriented to be a future Front Office Director at a large hotel.…
Added 10 mins ago
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Senior Analyst, Marketing Science
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- Full-time
Communicate with clients about media, data operations, measurement, competitive analysis, testing, modeling requirements, and results.
Added 10 mins ago
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Project Engineer (Laval)
Trane Italia
Laval, QC · Longueuil, QC
- Full-time
…requirements. Works directly on the project team to assist the Project…
Added 25 mins ago
BG
Territory Manager
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Zehner
- Full-time
…satisfaction and project success. Work collaboratively with Operations Manger and other Territory Manager(s) to develop the territory sales…
Added 25 mins ago
C
Change Management Manager
Cella
Toronto, ON · Greater Toronto Area, Canada
- $40 to $46 CAD / hour
- Contract
…strategic partner to HR, Talent, Technology, Communications, Operations, and executive leadership. You will establish robust governance frameworks, conduct end-to-end readiness and impact…
Added 25 mins ago
Grocery Manager
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The Grocery Manager is responsible for coaching, motivating, and developing department staff to foster customer loyalty, fulfil customer needs and actively contribute to an environment of…
Added 25 mins ago
Access Control Coordinator - Casual
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As part of our Security Operations Centre(SOC) team, this role plays a key part in facilitating 24/7/365 event and operational service excellence to multiple internal departments,…
Added 25 mins ago
Customer Care Centre Agent - Winter 2026/27
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The Customer Care Centre Agent is in a visible role, handling all inbound calls to the Calgary Snow Central Office and main line of the Resort. The Agent facilitates pass and product sales,…

SysAid

Manager, Sales Enablement

Toronto, ON, Canada

Full-time

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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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