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Added 26 mins ago
S
Regional Sales Director
Salesforce
Toronto, ON · Canada - Toronto
- Full-time
…looking for Trailblazers who are passionate about bettering business and the world through AI, driving innovation, and keeping Salesforce's core values at the heart of it…
Added 26 mins ago
SP
Enterprise/Commercial Account Executive – Data Foundation (MuleSoft + Informatica) or Enterprise/Commercial Account Executive - Informatica Specialist
Salesforce Partner Canada
Toronto, ON
- Full-time
Business-value seller: Demonstrated ability to translate technical capabilities into executive-level business outcomes (revenue, risk mitigation, and market advantage).
Added 26 mins ago
SP
SMB Account Executive – Data Foundation (MuleSoft + Informatica) AE or Informatica Specialist AE (Toronto)
Salesforce Partner Canada
Toronto, ON
- Full-time
Business-value seller: Demonstrated ability to translate technical capabilities into executive-level business outcomes (revenue, risk mitigation, and competitive advantage).
Added 27 mins ago
SP
Regional Sales Director
Salesforce Partner Canada
Toronto, ON
- Full-time
As a Sales Leader, you will manage and develop a team of Account Executives. You will take part in and lead client and prospect meetings, and work cross-functionally with internal partners…
Added 42 mins ago
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Account Executive
Beneva
NS · Toronto, ON
- Full-time
Proven sales and business development ability, including comfort with numerical analysis.
Added 57 mins ago
Industry Advisor - Public Safety
Softchoice
Ottawa, ON
…within the organization, helping shape strategies to enhance sales performance. This hybrid role requires approximately 25% travel, including occasional travel to the United States,…
Added 57 mins ago
M&
Entry-Level Commercial Real Estate Agent
Marcus & Millichap
AB · Edmonton, AB
- Full-time
…at the highest level. From day one you are building your own business in commercial real estate investment sales. You do not need industry experience to start. You need drive, discipline,…
Added 1 hour ago
AR
Community Business Manager
Atria Retirement Canada - View at Lethbridge
Lethbridge, AB · AB-Lethbridge
- Full-time
…of general ledger and monthly financials in conjunction with Executive Director.• Work in conjunction with the Executive Director with the preparation of operational and financial variance…
Added 1 hour ago
AC
Chief Executive Officer, Winnipeg Insurance Brokers
Assiniboine Credit Union
Winnipeg, MB
- Full-time
Guided by Winnipeg Insurance Brokers Ltd. mission and values, the Chief Executive Officer (CEO, WIB) leads and directs a multi-branch insurance brokerage. This position maintains overall…
Added 1 hour ago
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Senior Marketing Manager
PwC
Toronto, ON
- Full-time
As a Senior Marketing Manager, you will lead the development and delivery of integrated B2B marketing strategies that advance PwC Canada’s business priorities. You will partner with senior…
Added 1 hour ago
ES
Director of Engineering & Technical Services
Engineering Search Firm Inc.
Hanover, ON
- Full-time
· Work with Executive Leadership to make decisions for operational activities and execute strategic planning and goals for the business.
Added 1 hour ago
PC
Personal Lines Account Executive
People Corporation
Toronto, ON · ON - PC John St - Toronto
- Full-time
Experience in a quota-driven sales environment, business development, or client-facing sales.
Added 1 hour ago
I
Directeur adjoint, Architecture de solutions d’IA/ Associate Principal, AI Solution Architecture
IQVIA
Ottawa, ON
- Full-time
…operationally scalable, and demonstrably trustworthy. Working across business development, consulting, engineering, product, and applied science teams, the Associate Principal translates…
Added 1 hour ago
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Enterprise Account Executive - Toronto
HiBob
Toronto, ON
- Full-time
Working cross-functionally with Sales Engineering, Business Development, and Customer Success, you will own the end-to-end sales cycle - from strategic outbound prospecting to complex deal…
Added 1 hour ago
Y
Sales Development Representative (SDR) - Outbound B2B
YuJa
Toronto, ON · North York, ON
- $60,000 to $70,000 CAD / year
- Full-time
This is an expansion role designed to support the continued growth and scaling of our Sales Development team. Our Sales Development team members are at the forefront of our growth,…
Added 2 hours ago
MC
Director, Advisor Experience
Meridian Credit Union
St. Catharines, ON · Toronto, ON · Etobicoke, ON
- Full-time
Partner with Sales Effectiveness, Learning and RVPs to activate and continuously amplify coaching frameworks, business-planning disciplines and leader routines. Set strategic priorities for…
Added 2 hours ago
MC
Director, Distribution & Activation
Meridian Credit Union
St. Catharines, ON · Toronto, ON · Etobicoke, ON
- Full-time
The role: Accelerates growth by leading development, prioritization and commercial mobilization of Wealth-specific growth programs, including referral and lead ecosystems, advisor…
Added 2 hours ago
LC
Outbound Account Executive (Hospitality)
Lightspeed Commerce, Inc.
Remote, Canada
- Full-time
- Remote
This is a full cycle Account Executive (AE) role. AE’s will be generating a pipeline through prospecting, booking meetings and owning the sales processing from initial outreach to demo and…
Added 2 hours ago
LC
Outbound Account Executive (Hospitality)
Lightspeed Commerce, Inc.
Remote, Canada
- Full-time
- Remote
This is a full cycle Account Executive (AE) role. AE’s will be generating a pipeline through prospecting, booking meetings and owning the sales processing from initial outreach to demo and…
Added 2 hours ago
DN
Director, Business Development & Capture
Des Nedhe Group Defence
Ottawa, ON
- Full-time
Minimum 10 years of progressively responsible experience in defence or security business development, corporate development, major-program capture or strategic growth, with demonstrated…
Added 2 hours ago
CC
Director, Leadership Giving
Canadian Cancer Society
Vancouver, BC
- Full-time
Reporting to the Senior Executive Director, Leadership Giving, the Director, Leadership Giving, British Columbia will build the capacity for donor relationship management across British…
Added 2 hours ago
B
Portfolio Real Estate Strategy Manager
BGIS
Montreal, QC
- Full-time
Analyze, evaluate, present and advocate for new development or sales opportunities which support the organization goal, including office space, technical space, land, towers sites, media…
Added 2 hours ago
CE
Market Leader / Chef de Marché - Alberta and Saskatchewan / Alberta et Saskatchewan
Carrier Enterprise Canada
SK · Saskatchewan, Canada
- Full-time
Establish and maintain executive-level customer relationships to advance business development opportunities.
Added 2 hours ago
Territory Account Executive, Halifax
Block
Halifax, NS
Square is building a best-in-class, high-impact field sales organization, and we are looking for an exceptional Territory Account Executive - someone who consistently exceeds expectations,…
Added 2 hours ago
S
Business Developer Manager
Siemens
Montreal, QC
- Full-time

SysAid

Sales Enablement Manager

Toronto, ON, Canada

Full-time

Apply About employer

Applications open in a new tab.

Job details

Job type: Full-time
Apply by: Oct 26, 2027
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

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 and build an AI-first enablement model using Claude and connected systems to support onboarding, coaching, content, and seller workflows. Measure enablement impact against revenue outcomes, manage the GTM technology stack, and align sales messaging and readiness across regions and teams.

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 a proven record of 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 analytics, and be based in or willing to relocate to Toronto.

Skills

Sales Enablement
Sales Strategy
Sales Coaching
AI Workflow Automation
Claude and LLM Tools
Agentic Workflows
Salesforce
Gong
Snowflake
Sales Messaging
Content Strategy
Revenue Analytics
Sales Readiness
Go-to-Market Strategy
Communication and Presentation
Learning and Development

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
Artificial Intelligence
Claude
MCP
LLMs
Agentic Workflows
Salesforce
Gong
Snowflake
Lemlist
Clay
ZoomInfo
Juno
Accord
Revenue Operations
IT Service Management
SaaS
B2B Technology Sales
Sales Readiness
Sales Coaching
Sales Methodology
Go-to-Market Strategy
Sales Messaging
Content Management
Learning Management Systems
Revenue Analytics
Sales Performance Metrics
Product Launch Readiness
Account Research
Objection Handling

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