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Added 9 mins ago
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Product Manager
MNP
AB · Calgary, AB
- Full-time
Make an impact with our Technology – Solution Delivery team as a Product Manager. This diverse team of tech-savvy builders and problem solvers embraces digital transformation, and the…
Added 23 mins ago
CT
Associate Manager, Loyalty Program
Canadian Tire Corporation
Toronto, ON
- Full-time
Lead cross-functional initiatives: Mobilize partners across Product, Marketing, Analytics, Finance, Research, Operations and other teams to deliver loyalty initiatives, pilots and program…
Added 39 mins ago
WC
Gestionnaire de produits, Composants de matériel roulant (RSC) / Rolling Stock Components (RSC) Product Manager
Wabtec Corporation
Montreal, QC
- $95,000 to $127,000 CAD / year
- Full-time
…comptes clés, de développement des affaires, de soumissions, d'opérations commerciales (COM-OPS), d'ingénierie de produits, d'approvisionnement, d'exploitation et de services au sein de la…
Added 39 mins ago
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Senior Director, Clinical Development Change & Transformation Lead
Evinova
Mississauga, ON
- Full-time
…across clinical development. Working within the transformation strategy and roadmap set by Evinova's Clinical Development Digital Innovation & Transformation leadership, you will lead the…
Added 54 mins ago
GM
Business Operations & Product Development Manager
Global Medical Products Inc.
Burlington, ON
- Full-time
We are seeking a Business Operations & Product Development Manager to play a key role in strengthening our day-to-day operations, driving strategic initiatives, and expanding our product…
Added 1 hour ago
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Tax Manager
STEMCELL Technologies
Burnaby, BC · Canada - BC, Burnaby, Production Court, Onsite
- Full-time
Are you passionate about supporting research to cure disease? STEMCELL Technologies is hiring a Tax Manager to help lead our global tax operations as we continue to grow.
Added 1 hour ago
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Business Manager
FCC / FAC
AB · Edmonton, Alberta
- Full-time
As a Business Manager, you'll play a key role in supporting the execution of FCC's strategy by working closely with two Vice-Presidents and their leadership teams. You'll provide analysis,…
Added 1 hour ago
Tangerine Advisor - Bilingual (French/English) - Tangerine
Scotiabank
Toronto, ON
…and E-services when needed. They will report directly to the Manager of Tangerine…
Added 2 hours ago
MU
Project Manager, Graduate Education Initiatives
McGill University
Victoria, BC · James Admin. Bldg.
- Full-time
Reporting to the Director Strategy & Operations, the Project Manager, Graduate Education Initiatives provides advising, planning, policy and project management support on a range of…
Added 2 hours ago
FC
Market Data Vendor Manager
Fidelity Canada
Toronto, ON
- Full-time
2.Market Data Administration & Operations: Oversee day-to-day market data administration activities, including onboarding/offboarding, entitlement management, invoice validation, inventory…
Added 2 hours ago
GT
Manager, Operational Modernization
Greater Toronto Airports Authority
Toronto, ON
- Full-time
8+ years of progressively responsible experience in operations, operational planning, process improvement, capacity planning, business transformation, or strategy execution.
Added 3 hours ago
Sales Manager, Canadian Armed Forces (CAF)
Octasic
Montreal, QC
Reporting to the Director Sales CAN and EMEA; Sales Manager, Canadian Armed Forces (CAF), is responsible for developing and executing Octasic's growth strategy across the Canadian defense…
Added 3 hours ago
IG
Brand Marketing Specialist
Insight Global
Brampton, ON
- $22 to $24 CAD / hour
- Contract
Brand communications, creative & media strategy (traditional and digital media)
Added 3 hours ago
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Sales Manager, Canadian Armed Forces (CAF) / Directeur des ventes
Octasic
Ottawa, ON
- Full-time
Reporting to the Director Sales CAN and EMEA; Sales Manager, Canadian Armed Forces (CAF), is responsible for developing and executing Octasic's growth strategy across the Canadian defense…
Added 3 hours ago
CI
Manager, Finance
Canadian Institute for Safety, Wellness, and Performance (CISWP)
Cambridge, ON
- $115,000 to $130,000 CAD / year
- Full-time
The Manager, Finance is responsible for leading the Institute's financial operations while providing strategic financial guidance to support organizational sustainability, growth, and…
Added 3 hours ago
TH
Patient Flow Coordinator (Temporary Full-Time)
Trillium Health Partners
Mississauga, ON
- Full-time
In collaboration with the Clinical Manager, develop daily flow strategy that is responsive in real time to competing capacity demands and changes in unit/patient acuity
Added 3 hours ago
S
Manager, Sales Enablement
SysAid
Toronto, ON
- Full-time
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,…
Added 4 hours ago
S
Absence, Time Tracking & Payroll Lead, BC Health Workday
Sanya’k̓ula
BC · British Columbia, Canada
- Full-time
…software solution as part of the BC Health Human Resources Strategy to transform HR services. Designed by Workday Canada, the new provincial platform will replace existing HR and payroll…
Added 4 hours ago
S
Senior Business Analyst, Business Functions, BC Health Workday
Sanya’k̓ula
BC · British Columbia, Canada
- Full-time
…software solution as part of the BC Health Human Resources Strategy to transform HR services. Designed by Workday Canada, the new provincial platform will replace existing HR and payroll…
Added 4 hours ago
S
Manager, Business Function Products, BC Health Workday
Sanya’k̓ula
BC · British Columbia, Canada
- Full-time
…software solution as part of the BC Health Human Resources Strategy to transform HR services. Designed by Workday Canada, the new provincial platform will replace existing HR and payroll…
Added 4 hours ago
PH
Reporting Architect, BC Health Workday
Provincial Health Services Authority
BC · British Columbia, Canada
- Full-time
…software solution as part of the BC Health Human Resources Strategy to transform HR services. Designed by Workday Canada, the new provincial platform will replace existing HR and payroll…
Added 4 hours ago
PH
Manager, 3D Printing & Clinical Engineering
Provincial Health Services Authority
Vancouver, BC
- Full-time
The 3D Printing & Clinical Engineering Manager provides strategic, operational, and technical leadership for the Clinical Technology Innovation (CTI) Program, with a specific focus on…
Added 5 hours ago
S
Organ Recovery Assistant, Organ Donation & Hospital Development - BC Transplant Society
Sanya’k̓ula
Vancouver, BC
- Part-time
Reporting to the Clinical Operations Manager, Organ Donation, the Organ Recovery Assistant (ORA) functions as an integral part of the Organ Donation and Hospital Development (ODHD) team.
Added 6 hours ago
AP
Clinical Operations Manager-Traveling CRC Team
ActivMed Practices & Research, LLC.
Burlington, ON
- Full-time
The Manager, Clinical Operations – Traveling Team is responsible for the coordination and execution of clinical research support at various site locations
Added 10 hours ago
GM
bakery manager - retail
Grey Matlock Bakery
Mississauga, ON
- Full-time
Study market research and trends to determine consumer demand, potential sales volumes and effect of competitors' operations on sales

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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