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Added 5 mins ago
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Engagement Manager
Straive
Calgary, AB
- Full-time
Job Tittle- Engagement Manager – Analytics and AI Consulting
Added 5 mins ago
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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 5 mins ago
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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 5 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 5 mins ago
Technical Program Manager-II, GO-AI
Amazon
Vancouver, BC
As a Technical Program Manager on GO-AI's Technology & Development team, you will partner with product, science, software engineering, data engineering, operations, and other Amazon…
Added 5 mins ago
RB
Manager, Digital Product Marketing - RBC Direct Investing
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Toronto, ON
- Full-time
As Manager, Digital Product Marketing, you will be a key product marketer on the Digital Marketing team, responsible for the web experience and content transformation of RBC Direct…
Added 5 mins ago
AG
Senior Analyst, Marketing Science
Adelphi Group
Toronto, ON
- Full-time
Lead a small team of Analysts and draw from wider Data Analytics resources within the organization, including Data Engineering
Added 20 mins ago
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Accounting Manager
Nanalysis
Calgary, AB · Greater Calgary Metropolitan Area
- Full-time
Nanalysis is seeking a detail-oriented Accounting Manager with an active Chartered Professional Accountant (CPA) designation to support month-end close, financial reporting under IFRS…
Added 35 mins ago
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Pricing Manager
Pet Valu
Markham, ON
- Full-time
The Pricing Manager is responsible for supporting the development, execution, and continuous improvement of pricing strategies that drive sales, profitability, and customer value. Working…
Added 35 mins ago
UO
Programmer Analyst II
University of British Columbia
Vancouver, BC · UBCV | The Leonard S. Klinck Building (LSK)
- $8,810.92 to $13,202.5 CAD / month
- Full-time
The incumbent is a member of the Enterprise Automation and Solution Delivery (EASD) team, reporting to the Senior Manager, EASD. Work may also be directed and reviewed by a Delivery Manager…
Added 35 mins ago
UO
Programmer Analyst II
University of British Columbia
Vancouver, BC · UBCV | The Leonard S. Klinck Building (LSK)
- $8,810.92 to $13,202.5 CAD / month
- Full-time
The incumbent is a member of the Enterprise Automation and Solution Delivery (EASD) team, reporting to the Senior Manager, EASD. Work may also be directed and reviewed by a Delivery Manager…
Added 35 mins ago
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Software Engineer III
TD
Toronto, ON
- Full-time
Added 35 mins ago
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Software Engineer II
TD
Toronto, ON
- Full-time
Added 35 mins ago
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Senior Consultant, AI Strategy & Program Execution
Sun Life
Toronto, ON · Waterloo, ON · Sun Life Waterloo King
- Full-time
…execution. In addition, they will serve as the primary program manager for an assigned AI workstream within the portfolio, coordinating stakeholders and ensuring priorities translate into…
Added 35 mins ago
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Gestionnaire, Médias
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Montreal, QC
- Full-time
…plateformes de médias numériques (Google Ads, Meta Business Manager, DV360 et Campaign Manager 360), des outils d’analytique (Google Analytics) et des plateformes de gestion des enchères…
Added 50 mins ago
M
Strategic Partnership Manager
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Halifax, NS · Toronto, ON · Waterloo, ON · Montreal, QC
- Full-time
As a Strategic Partnership Manager, you will play a critical role in leading initiatives, driving high value vendor relationships, optimizing third-party performance, and enabling strong…
Added 50 mins ago
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Senior Product Manager
Litera
Toronto, ON · Canada-Toronto, ON-Office
- Full-time
As a Senior Product Manager, you’ll own the vision, strategy, and roadmap for Litera’s Firm Intelligence Platform - the foundational layer that turns the data flowing through a law firm’s…
Added 50 mins ago
HD
Amazon Brand Manager
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Remote, Canada
- Full-time
- Remote
Hadley Designs is seeking an Amazon Brand Manager to take full ownership of a multi-million dollar group of our products on Amazon, as the product manager, the merchandiser, and the CEO of…
Added 51 mins ago
PC
Junior Compliance Manager ( Calgary, AB)
Phantom Compliance
Crowsnest Pass, AB
- Full-time
Eagerness to learn blockchain analytics, transaction monitoring workflows, and risk assessment models.
Added 51 mins ago
PC
Service Delivery Manager ( Blairmore, AB)
Phantom Compliance
Crowsnest Pass, AB
- Part-time
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Added 51 mins ago
EB
Account Specialist, Sales, Canada
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- Full-time
The Account Specialist, Sales will assist the Account Manager(s) with bringing e.l.f. Cosmetics and e.l.f. SKIN to life within our retailers in Canada. The role supports all customer…
Added 51 mins ago
S
Senior Software Engineering Manager
symplistic.ai
Woodbridge, ON
- $150,000 CAD / year
- Full-time
We seek a hands-on Engineering Manager to lead ContentIQ's development, quality, delivery, and operation. You'll mentor engineers while actively coding, making architectural decisions, and…
Added 51 mins ago
RI
Growth Marketing Manager
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Newmarket, ON
- Full-time
Reporting to the General Manager, we are hiring a Growth Marketing Manager to establish and lead our in-house marketing function across Realtax and Ontario Tax Sales. As our new Growth…
Added 1 hour ago
Principal Strategic Deal Maker- Sales Executive
Capgemini
Mississauga, ON
The manager will be responsible for the following key activities:
Added 1 hour ago
MI
Director of Product
Method Integration Inc.
Remote, Canada
- Full-time
- Remote
Own the product plan, from the long-term big picture down to what ships next, and hold every Product Manager to the same standard: work is thought through and grounded in customer data…

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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