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Added 4 mins ago
Q
Business Development Manager/Field Sales - (Parcel Lockers) - Vancouver, BC, Canada
Quadient
Vancouver, BC
- $80,000 to $108,196 CAD / year
- Full-time
As a Business Development / Site Acquisition Manager, you will play a critical role in expanding our parcel locker footprint by identifying, securing, and developing high-value locations…
Added 4 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 4 mins ago
GA
General Manager, AX Metrotown
Giorgio Armani
Burnaby, BC
- Part-time
As a General Manager you will also provide input on merchandising, marketing, and client relationship strategies. Your presence daily on the sales floor will provide you the opportunity to…
Added 18 mins ago
SM
RQ11680 – Systems Analyst – Senior
S M Software Solutions Inc
Toronto, ON
- Internship
…hands-on knowledge of PeopleSoft HCM upgrades, PeopleSoft Update Manager (PUM), PeopleTools upgrades, Fluid and Classic+ interfaces, and HR-related modules, including Absence Management,…
Added 19 mins ago
PJ
General Manager, International Markets (MEA)
Papa Johns
NB · Chiasson Office, NB
- Full-time
The General Manager, International Markets (MEA) is the senior leader responsible for driving the sustainable growth, profitability, and long-term success of the Papa Johns business across…
Added 19 mins ago
CC
Regional Branch Manager
Crossroads C&I
Saint John, NB
- Full-time
…company's values, our Branch Managers direct and manage all branch operations and resources with the overall responsibility to achieve maximum profits consistent with the company’s business…
Added 19 mins ago
B|
Gestionnaire des opérations | Operations Manager
Bloom | Digital Marketing Agency
Montreal, QC
- Full-time
Nous recherchons un(e) gestionnaire des opérations très organisé(e), calé(e) en technologie et adaptable pour superviser et optimiser les systèmes internes, les outils numériques et les…
Added 19 mins ago
D
Recruitment Manager
Delpath
Toronto, ON
- Full-time
…of service, we are looking for a high-performing Recruitment…
Added 19 mins ago
CC
Regional Branch Manager
Crossroads C&I
Dartmouth, NS
- Full-time
…company's values, our Branch Managers direct and manage all branch operations and resources with the overall responsibility to achieve maximum profits consistent with the company’s business…
Added 33 mins ago
B
Gestionnaire des opérations | Operations Manager
Bloom
Montreal, QC
- Full-time
Nous recherchons un(e) gestionnaire des opérations très organisé(e), calé(e) en technologie et adaptable pour superviser et optimiser les systèmes internes, les outils numériques et les…
Added 33 mins ago
B
Credit Analyst
BMO
Toronto, ON · FCP
- Full-time
Builds and maintains client relationships to ensure long-term financial performance in collaboration with Relationship Manager and business partners.
Added 33 mins ago
RG
Director, FP&A
Regional Group
Ottawa, ON
- Full-time
…in development, construction, asset management, and property operations to deliver exceptional value and experiences. Through our homebuilding division, eQ Homes, we continue to set the…
Added 33 mins ago
A
SOC Manager (Secret Cleared)
Accenture
Ottawa, ON
- Full-time
The primary objective of the SOC manager is to manage SOC operations for our external clients, in transition of service and/or in the run-phase of the service. This role is responsible to…
Added 33 mins ago
C
General Manager - Galaxy Moose Jaw
Cineplex
Moose Jaw, SK · GLX Moose Jaw
- Full-time
…exceptional experience to each and every guest. The General Manager executes all company programs, supports the operation of the business, maintains revenue and payroll budgets, and meets…
Added 48 mins ago
JC
Manufacturing Operations Manager
Johnson Controls
AB · SA - Edmonton Orion
- Full-time
You will be responsible for the strategic direction, leadership, and overall administration of plant operations overseeing staffing and production while effectively and efficiently…
Added 48 mins ago
G
Process Owner Assembly
gategroup
Mississauga, ON · CAN_ON_Mississauga_YYZ
- Full-time
…Assembly processes/department within the Gate Gourmet Large operations. The Individual is a strong leader with strong People management…
Added 1 hour ago
LC
Inbound Sales Development Representative - Hospitality
Lightspeed Commerce, Inc.
Remote, Canada
- Full-time
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…have with our sales team. You will be responsible for driving revenue growth by generating and qualifying leads for the sales team. The ideal candidate will have experience generating leads…
Added 1 hour ago
LI
Manager of Payroll and Benefits (Global)
Loopio Inc.
Remote, Canada
- $110,000 to $140,000 CAD / year
- Full-time
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…People team, you will at times work closely with Sales and Revenue Operations, especially for Variable compensation…
Added 1 hour ago
HS
President
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ON · Niagara, ON
- Full-time
5+ years in a senior executive role (e.g., General Manager, Vice President of Operations, COO, or President).
Added 1 hour ago
O
National Accounts Director
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- $100,000 to $125,000 CAD / year
- Full-time
A National Account Director who will serve as the primary account relationship manager for commercial sellers. The core focus of this role is (1) to retain our high-value client base to…
Added 1 hour ago
I
Finance Manager
InnPower
Innisfil, ON
- Full-time
Responsible for managing the day-to-day operations of Finance. Includes keeping or causing proper financial records to be kept, managing general accounting, payroll, accounts payable,…
Added 1 hour ago
A
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Toronto, ON
- Full-time
…other organizations build their digital core, optimize their operations, accelerate revenue growth and enhance citizen services - creating tangible value at speed and scale. We are a…
Added 1 hour ago
O
Property Administrator
OMERS
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- Full-time
We are a leading global real estate investor, developer and manager. We combine our capital with our capabilities to create real estate that strengthens economies and communities. By…
Added 1 hour ago
DI
Manager, ABM & Paid Digital
Dig Insights
Toronto, ON · Greater Toronto Area, Canada
- Full-time
…you will set ABM goals tied to account warmth, pipeline, and revenue targets, and you will coordinate with content and subject matter experts to ensure campaigns are supported by relevant…
Added 1 hour ago
K
Store Manager, Toronto
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SysAid

Manager, Sales Enablement

Toronto, ON, Canada

Full-time

Apply About employer

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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