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Added 3 mins ago
BL
Paid Media Acquisition and Growth Specialist
Blanc Labs
Toronto, ON
- Contract
…next-generation digital products and services. Our expertise in digital transformation powers businesses to accelerate service delivery, drive customer engagement, and foster…
Added 3 mins ago
IF
Director, IT Service Delivery, Talent and Culture, Treasury and Banking Services
iA Financial Group
Montreal, QC · Quebec, QC
- Full-time
Are you passionate about technological transformation and eager to contribute to the purpose of an organization committed to helping its clients feel confident and secure about their future?
Added 3 mins ago
M
Comptable, Inventaire / Accountant, Inventory
McKesson
Montreal, QC
- Full-time
…tiers et contribuerez à l’amélioration des processus et à la transformation numérique au sein de la fonction…
Added 18 mins ago
IC
Cloud Operations, Senior Specialist
Interac Corp.
Toronto, ON · Interac Corp. Head Office
- Full-time
Lead hands-on AWS operational engineering across Interac’s cloud environments, with responsibility for Terraform-based infrastructure automation, production reliability, observability,…
Added 18 mins ago
SH
Manager/Director, Management Consulting
Santis Health
Toronto, ON
- Full-time
…lasting impact. The successful candidate will originate and lead client engagements, build and develop high-performing teams and help define the service offerings that drive the practice’s…
Added 34 mins ago
MarTech / AdTech Technical Lead
Capgemini
Mississauga, ON
As a MarTech / AdTech Technical Lead, you will lead solution design and technical delivery across the marketing and advertising technology ecosystem, including customer data platforms…
Added 48 mins ago
Enterprise Architect
Sobeys Capital Incorporated or a Franchise/Affiliate / ou une franchise/société affiliée
Calgary, AB · Stellarton, NS · Mississauga, ON
…health, guide major technology decisions, and support strategic transformation…
Added 1 hour ago
B
Senior Data Migration SME
Bevertec
ON · Ontario, Canada
- Contract
Advanced proficiency in Python and SQL for data processing, transformation, validation, and reconciliation.
Added 1 hour ago
C
Pre-Sales D365 / ERP Solutions Architect
Centrilogic
Canada
- Full-time
Engage with C-level executives to address infrastructure, security, and transformation concerns.
Added 1 hour ago
S
Enterprise Architect – AI, Data & Cloud
Synechron
Mississauga, ON
- $180,000 to $200,000 CAD / year
- Full-time
…an advisory leader. They will shape enterprise architecture, lead critical design decisions, review architecture-critical implementations, mentor architects and engineers, evaluate emerging…
Added 1 hour ago
H
Accounts Payable Lead
Hitachi
Toronto, ON · (RSBU) Toronto
- Full-time
…of the world, our work goes to the cutting-edge of digital transformation and technology. From the multi-cultural strength of our global organisation to the sustainable and innovative ways…
Added 1 hour ago
RH
Marketing Manager
Robert Half
Oshawa, ON
- $85,000 to $95,000 CAD / year
- Full-time
Lead CRM, email marketing, and marketing automation initiatives, including customer segmentation, personalized campaigns, automated journeys, and retention strategies.
Added 2 hours ago
AS
AWS Cloud Architect
Ardent SoftSol Inc.
Mississauga, ON
- $50 to $55 CAD / hour
- Contract
Lead API-first transformation initiatives across business domains.
Added 2 hours ago
JG
AWS / API lead and Architect
J&M Group
Mississauga, ON
- Contract
Lead API-first transformation initiatives across business domains.
Added 2 hours ago
Q
Business Development Manager/Field Sales - (Parcel Lockers) - Vancouver, BC, Canada
Quadient
Vancouver, BC
- $80,000 to $108,196 CAD / year
- Full-time
At Quadient, we support businesses of all sizes in their digital transformation and growth journey, unlocking operational efficiency with reliable, secure, and sustainable automation…
Added 2 hours ago
I
Senior Sales Director
Infosys
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Lead sales of Finacle Core Banking, Digital Banking, Payments, Lending, and Banking Transformation solutions.
Added 2 hours ago
FG
Lead Software Engineer, Full-Stack Applications - AI Fluent
Fitch Group
Toronto, ON
- $180,000 to $220,000 CAD / year
Lead Software Engineer, Full-Stack Applications – AI Fluent
Added 2 hours ago
S
Solution Engineer (Pre-Sales) - All Levels (Canada)
Salesforce
Toronto, ON
- Full-time
Ready to level-up your career at the company leading workforce transformation in the agentic era? You’re in the right place! Agentforce is the future of AI, and you are the future of…
Added 2 hours ago
N
Director, Global Trade Credit
Nutrien
Calgary, AB
- Full-time
We are seeking a Director, Global Trade Credit to lead credit risk management for a large portfolio of corporate customers across North America, with select international exposure. This…
Added 2 hours ago
S
Manager, Sales Enablement
SysAid
Toronto, ON
- Full-time
…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…
Added 2 hours ago
XI
Senior Engineering Manager
Xplore Inc.
Markham, ON
- Full-time
We are looking for an experienced Senior Engineering Manager to lead and grow a team of software developers as we embark on a company-wide transformation. This is your chance to use…
Added 3 hours ago
S
Data Scientist
SymphonyAI
Toronto, ON
- Full-time
Better models lead to better decisions, stronger controls, and safer financial systems. That’s where you come in.
Added 4 hours ago
IF
Senior Process Journey Owner
iA Financial Group
Toronto, ON · Montreal, QC
- Full-time
Are you driven by digital transformation and eager to improve the experiences of advisors and clients? As a Senior Process Journey Owner, you will lead the evolution of business processes…
Added 4 hours ago
HT
VP, Accounting & Controllership (Husky)
Husky Technologies
Bolton, ON
- Full-time
…passion of our people around the world and their desire to lead change. At the same time, we are not afraid to expect a lot and strive for leadership in all of our key markets. We are a…
Added 5 hours ago
BT
IT & Innovation Consultant, SR&ED
Baker Tilly Canada
Windsor, ON
- Full-time
Lead client interviews with developers, technical leads, project managers, and business owners, asking clear follow-up questions to gather complete and accurate technical information.

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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