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Added 12 mins ago
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Manager, Systems Development - Agentic Salesforce Delivery
Co-operators
Guelph, ON · Mississauga, ON · Toronto, ON
- Full-time
As the Manager, Systems Development – Salesforce, you will lead teams of IT professionals and provide expert IT solution delivery advice and direction to the organization, with a focus on…
Added 42 mins ago
Senior Manager, Business Banking Deposits Product Management - Tangerine
Scotiabank
Toronto, ON
The Senior Manager, Small Business Deposit Products is accountable for supporting the execution of Tangerine’s Small Business deposits strategy and product roadmap. The role will help…
Added 1 hour ago
ST
Sales Enablement Manager
SysAid Technologies
Toronto, ON
- Full-time
Build, test and improve agentic enablement workflows end to end, and measure accuracy, adoption and business results.
Added 1 hour ago
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Sales Enablement Manager
SysAid
Toronto, ON
- Full-time
Build, test and improve agentic enablement workflows end to end, and measure accuracy, adoption and business results.
Added 1 hour ago
OS
Marketing Director
OneRiver Software
Toronto, ON · Greater Toronto and Hamilton Area, ON
- Full-time
Develop sales enablement materials, ROI and business-case tools, case studies, presentations, and competitive intelligence.
Added 1 hour ago
R
Client Advisor
RBC
Carman, MB
- Part-time
…individual needs. You will champion the RBC brand and drive business by supporting new client acquisition and deepening existing relationships. If you have the self-motivation to deliver…
Added 2 hours ago
CO
Sr. Manager, Artificial Intelligence 1
City of Brampton
Brampton, ON
- Full-time
Transformative delivery. Partner with business, IT and Digital Enablement teams to identify and execute opportunities, align with enterprise architecture and measure service and operational…
Added 2 hours ago
ZG
General Manager / Head of Vision Care Canada
ZEISS Group
Toronto, ON
- Full-time
How many companies can say they’ve been in business for over 180 years?!
Added 2 hours ago
AF
Senior Manager, Cloud & AI Security
ATB Financial
Calgary, AB
- Full-time
As ATB’s next Senior Manager, Cloud & AI Security, you’ll lead a team responsible for securing ATB’s cloud platforms and enabling the safe adoption of AI. You’ll set the security roadmap,…
Added 3 hours ago
Gainsight Administrator
Braze
Toronto, ON
Partner cross-functionally: Work with the CX Business Systems Analyst / Technical Project Manager team and CX Operations, who gather and shape requirements, and provide the…
Added 3 hours ago
B
Gainsight Administrator
Braze
Toronto, ON
- Full-time
Partner cross-functionally: Work with the CX Business Systems Analyst / Technical Project Manager team and CX Operations, who gather and shape requirements, and provide the…
Added 3 hours ago
DC
Power BI & Power Platform Administrator
Dasro Consulting Inc.
Calgary, AB
- Contract
Manage platform-level Copilot enablement, environment configurations, and credit consumption tracking/forecasting.
Added 3 hours ago
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AVP, Programs & Deployment
TD
Toronto, ON
- Full-time
As the business integrator for the portfolio, the role connects enterprise priorities, planning excellence, client experience, field enablement, operating model evolution, and business…
Added 3 hours ago
M
Product Marketing Manager
MapsPeople
Richmond Hill, ON
- Full-time
…across the Americas, we are looking for a Product Marketing Manager to strengthen how we position our platform, bring new capabilities to market, enable our sales organization, and connect…
Added 4 hours ago
Senior Product Marketing Manager, Marketing & Operations Audiences
Asana
Vancouver, BC
The Asana Product Marketing team fuels business growth and builds a brand customers love by creating campaigns and content to attract new accounts and inspire current ones to grow with us.…
Added 4 hours ago
Senior Product Marketing Manager, IT and AI Transformation
Asana
Vancouver, BC
The Asana Product Marketing team fuels business growth and builds a brand customers love by creating campaigns and content to attract new accounts and inspire current ones to grow with us.…
Added 4 hours ago
RB
Client Advisor
Royal Bank of Canada
NS · ST. MARY'S, Nova Scotia
- Part-time
…individual needs. You will champion the RBC brand and drive business by supporting new client acquisition and deepening existing relationships. If you have the self-motivation to deliver…
Added 4 hours ago
L
Logistics and Compliance Analyst
Longo's
Vaughan, ON
- Full-time
Reporting to the Replenishment Manager. The Logistics & Compliance Analyst is responsible for driving supply chain performance through the integration of demand planning, advanced…
Added 4 hours ago
J&
IM Transcend-Program Manager, Signavio
Johnson & Johnson Innovative Medicine
Toronto, ON
- Full-time
Transcend is a global business transformation program that will modernize our foundational transactional processes and harmonize them into one “clean” ERP as a standardized platform for…
Added 4 hours ago
BQ
QNX Quality Manager
BlackBerry QNX
Ottawa, ON
- Full-time
…trusted foundation for software-defined businesses to thrive. The business leads the way in delivering safe and secure operating systems, hypervisors, middleware, solutions, and development…
Added 4 hours ago
B
QNX Quality Manager
BlackBerry
Ottawa, ON
- Full-time
…trusted foundation for software-defined businesses to thrive. The business leads the way in delivering safe and secure operating systems, hypervisors, middleware, solutions, and development…
Added 5 hours ago
Partner Marketing Manager (Hybrid)
OpenTable
Toronto, ON
OpenTable is looking for a Partner Marketing Manager to turn strategic partnerships into repeatable, measurable growth for our restaurant business. Reporting to the Senior Director,…
Added 5 hours ago
A
Manager, Data Analytics and Reporting
AstraZeneca
Mississauga, ON · Canada - Mississauga
- Full-time
The Manager, Analytics & Reporting will lead the creation of trusted, scalable analytics and reporting that power the US Commercial business across Specialty Pharmacy, Specialty Infusion…
Added 5 hours ago
FM
AI Strategy Intern
Ford Motor Company
Oakville, ON
- Part-time
…intelligence strategy - both internally across Ford of Canada's business functions, and externally across our national dealership network. This is a unique opportunity to gain hands-on…
Added 5 hours ago
Manager, Performance Enablement - Global HR
Scotiabank
Toronto, ON
The Manager contributes to and support the development and execution of a global performance development strategy, program and processes that drive all key activities needed for a…

SysAid Technologies

Sales Enablement Manager

Toronto, ON, Canada

Full-time

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Job details

Job type: Full-time
Posting language: English
Posted: Oct 26, 2026

Original job 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

1. 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.

4. 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.

5. 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

You will architect and operate an AI-first enablement engine to drive global sales and customer success performance. This involves defining enablement strategy, designing AI-powered workflows, and aligning sales messaging with revenue goals.

Requirements

Candidates must have 5+ years of experience in B2B technology sales or enablement, including at least 3 years as a quota-carrying individual contributor. You must demonstrate hands-on experience with AI tools and modern GTM technology stacks.

Skills

Sales enablement
AI strategy
Claude
Salesforce
Gong
Revenue operations
Content strategy
Data analysis
B2B sales
Coaching
Workflow automation
Prompt engineering
Go-to-market strategy
Project management
Communication skills

Benefits

Medical insurance
Vision insurance
Dental insurance
RRSP
Life insurance
AD&D insurance
LTD insurance
Gender-neutral parental leave
Option plan

Visa sponsorship

Not detected in the job text

Keywords

Sales Enablement
AI-First
SaaS
ITSM
Claude
Salesforce
Gong
Snowflake
Lemlist
Clay
ZoomInfo
Juno
Accord
MCP
Revenue Operations
Go-to-market
B2B
Automation
Prompt Engineering
Sales Readiness
Coaching
KPIs
Workflow Design
Messaging Architecture
Data-driven
Customer Success
Product Launch
Sales Methodology
Toronto
Liberty Village

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