Senior Manager of Customer Success Enablement, Jobber

CA$132.4-179.1k

Our range is intentionally broad to support growth and long-term impact, with fully established hires typically starting around the midpoint ($155,700). The higher end of the range is reserved for those who have demonstrated deep expertise and lasting contributions, while offers below the midpoint reflect strong potential with room to develop+ Equity

Confluence

Notion

Senior and Expert level

Toronto

Vancouver

1+ day a week in office

Job tracking and customer management software for home service businesses

Open for applications

Job tracking and customer management software for home service businesses

1001+ employees

B2BCommunicationCustomer serviceFinancial ServicesSaaSMobile

Open for applications

CA$132.4-179.1k

Confluence

Notion

Senior and Expert level

Toronto

Vancouver

1+ day a week in office

1001+ employees

B2BCommunicationCustomer serviceFinancial ServicesSaaSMobile

Company mission

To help home service professionals around the world win.

Job

Company

Role

Who you are

This is a highly autonomous, impact-oriented role—ideal for someone who thrives in ambiguity, moves quickly from insight to action, and brings fresh, creative thinking to solving complex problems
You’re energized by building programs from the ground up, collaborating cross-functionally, and using data, feedback, and intuition to level up both team performance and the customer experience
You understand the inner workings of high-performing Success organizations and are ready to roll up your sleeves to build systems, content, and experiences that drive real results—whether it's a smoother ramp, a smarter knowledge base, or a more confident team on the front lines
Proven experience in enablement, L&D, or QA within a SaaS or customer-focused organization; demonstrated knowledge of relevant best practices, methodologies, and technologies
Proven leadership in building enablement strategies that serve diverse functions (e.g., onboarding, support, sales)
Deep experience with LMS platforms, content tools (e.g., Notion, Confluence), QA frameworks, and product enablement practices
A data-driven mindset and strong program management abilities
Ability to coach, mentor, and scale high-performing teams
Excellent communication and facilitation skills—across live sessions, async formats, and documentation
Strong business acumen
A high level of curiosity, and a passion for continuous improvement
Extremely strong analytical and problem-solving skills

What the job involves

We’re looking for a Sr. Manager, Enablement to be part of our Customer Success department
Our Customer Success team works together with other teams and stakeholders to bring our company values to life for our customers
By being humble, supportive, and truly giving a sh*t, the team ensures that our customers are successful in Jobber
This team thrives on meaningful and impactful communication with one another and with our customers and plays a significant role in the lives of entrepreneurs and business owners who utilize Jobber
The Enablement team is a central function within Jobber’s Customer Success organization, supporting the growth and performance of Customer Onboarding, Product Support and Account Management
As a Center of Excellence, Enablement owns the programs, tools, and frameworks that drive operational excellence and skill development in these areas
We work cross-functionally to ensure that every team member—regardless of channel or customer type—has the knowledge, confidence, and support to deliver value
As Senior Manager, Enablement, you’ll be a driving force behind the design and execution of enablement programs across employee onboarding, knowledge management, quality assurance, and continuous learning
You’ll play a pivotal role in shaping how our Customer Success teams onboard, grow, and show up for our customers across onboarding, support, and account management functions
Design and deliver onboarding, upskilling, and continuous learning programs tailored to the needs of Customer Onboarding, Product Support, and Sales Expansion teams
Coach Enablement team members in curriculum development, facilitation, and instructional design
Integrate feedback from Voice of Customer (VoC), QA insights, and CSAT metrics into training evolution
Oversee the creation, organization, and maintenance of internal and external knowledge assets (e.g., playbooks, SOPs, Help Center articles)
Ensure knowledge materials are accurate, accessible, and in line with best industry best practice for technical writing
Partner closely with Knowledge Base Managers and content specialists to drive strategy and efficiency in self-serve resources
Lead QA strategy for onboarding and support interactions, including call reviews, chat/email evaluations, and feedback loops
Align QA criteria with enablement outcomes and team performance standards
Drive cross-functional calibration sessions to ensure consistency and transparency
Define success metrics across each enablement pillar—ramp time, QA score trends, knowledge engagement, CSAT, and more
Report regularly on enablement impact to Success and cross-functional leadership
Use data to iterate on training delivery, content structure, and coaching programs
Partner with Product, Product Marketing, Operations, and People teams to ensure readiness for product releases, campaigns, and feature changes
Influence and support change management efforts across supported functions
Ensure enablement alignment with business goals, team targets, and customer outcomes

Our take

For businesses that sell home services, it can be difficult keeping up with paperwork, scheduling appointments, and chasing payments, especially when their teams are small. Jobber delivers a comprehensive toolbox to keep track of all these aspects, so that small business owners can concentrate on more important things like serving their customers and building their brand.

Jobber was founded in 2011, initially to help a friend who owned a small painting business. The founders quickly discovered that what they were building could help many more owners across a number of industries, going on to launch the product which is now used by over 300,000 home service professionals in over 60 countries.

What makes Jobber stand out is that it collects all the vital parts of running a home services business into one place, removing the burden of keeping track of multiple sources of information. The company has seen significant funding which it has invested in R&D and growing its customer base, and boasts four consecutive years on The Globe and Mail's Canada's Top Growing Companies List.

Steph

Company Specialist at Welcome to the Jungle

Insights

Top investors

15% employee growth in 12 months

Glassdoor (3.9)

Company

Funding (last 2 of 7 rounds)

Jan 2023

$100m

SERIES D

Jan 2021

$60m

GROWTH EQUITY VC

Total funding: $185.8m

Company HQ

Downtown, Edmonton, AB

Leadership

Sam Pillar

(Co-Founder & CEO)

Prior to co-founding Jobber in 2011, Sam was a Freelance Software Developer at Cardboard Creative and a Business Analyst/Management Consultant at CGI.

Forrest Zeisler

(Co-Founder & CTO)

Experienced Developer, with a degree in Engineering from the University of Alberta.

Salary benchmarks

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