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Added 1 min ago
H
Human Resources Generalist
Haivision
Montreal, QC
- Temporary
…the HR team on a variety of HR tasks. Reporting to the Senior Director of Human Resources and working closely with the Vice President of Finance, the HR Generalist will be assisting in…
Added 2 mins ago
C
Sr. Consultant, Business Effectiveness
CIBC
Toronto, ON
- Full-time
…such as Mortgage Advisor, Area Sales Manager, and Regional Director, while providing analysis related to targets, commissions, and channel performance. You'll partner closely with business…
Added 2 mins ago
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Director of Care (DOC) - Full Time (FT) - Charleswood Care Centre
Extendicare
Winnipeg, MB · Charleswood Care Centre
- Full-time
As the Director of Care, you will contribute to the Extendicare purpose of Helping People Live Better, by leading a high performing team that is dedicated to ensuring all residents receive…
Added 32 mins ago
TV
Director of Product Strategy and Commercialization
TandemLaunch Ventures Studio & Funds
Montreal, QC
- Full-time
We are hiring a Director of Product Strategy and Commercialization to be the product-and-market voice inside several of our ventures at once.
Added 32 mins ago
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Cost Assurance Specialist/ Cost Manager
Gleeds
Toronto, ON
- Full-time
This position will report directly to the Canada Operations Director.
Added 1 hour ago
TS
Associate, Transaction Banking Product Development
TD Securities
Toronto, ON
- Full-time
…Product Transformation team and will report directly to the Director, TB Payments, Product Transformation. The incumbent will require a detailed understanding the TB business, our client…
Added 2 hours ago
M
RQ00833 - Program Manager - Senior
Maarut
Toronto, ON
- Contract
Provide project oversight on behalf of the Director,
Added 5 hours ago
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Associate, Transaction Banking Product Development
TD
Toronto, ON
- Full-time
…Product Transformation team and will report directly to the Director, TB Payments, Product Transformation. The incumbent will require a detailed understanding the TB business, our client…
Added 6 hours ago
FH
Patient Care Coordinator, Mental Health & Substance Use Services (MH&SUS), In Patient Psychiatry - Chilliwack General Hospital
Fraser Health Authority
Chilliwack, BC
- $49.2 to $67.08 CAD / hour
- Full-time
…of telephone, virtual video/audio conference and/or remote technology to patients in their homes, in the community including outreach, and…
Added 8 hours ago
Dir Cyber Security Engineering
Altice USA
Toronto, ON
As the Director of Cyber Security Engineering, you will lead the strategic vision and implementation of advanced security frameworks, leveraging automation and AI/ML to enhance threat…
Added 9 hours ago
C
Data Scientist, Model Performance Monitoring and Reporting
CIBC
Toronto, ON
- Full-time
…artificial intelligence and leverage the latest in big data technology platforms. We also engage with the leading academic & research institutes in the space of AI and machine learning to…
Added 12 hours ago
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Director - Health Records - Regular Full-Time - 2026-18625 (2026-18625)
Sunnybrook
Toronto, ON
- Full-time
Reporting to the Vice President, Digital Health and Chief Information Officer, the successful candidate will be responsible for overseeing the management and strategic direction of the…
Added 12 hours ago
LS
District Visual Language Interpreter
Langley School District #35
Langley (District), BC · Langley, BC
- Full-time
Under the direction of the LSS director, or designate, the District Visual Language interpreter aids and support students, staff, and families in the district. The Educational Interpreter…
Added 12 hours ago
BV
Facilities Manager
Bow Valley College
Calgary, AB
- Full-time
…meaningful careers in health care, social services, business, technology, and creative industries. Every program has a Work Integrated Learning requirement, ensuring students contribute to…
Added 12 hours ago
BV
Infrastructure Analyst - Business Analyst II
Bow Valley College
Calgary, AB
- Full-time
…meaningful careers in health care, social services, business, technology, and creative industries. Every program has a Work Integrated Learning requirement, ensuring students contribute to…
Added 12 hours ago
FO
Finance Manager, Operations
Federation of Canadian Municipalities
Ottawa, ON · Hybrid - Ottawa
- Full-time
…financial processes. The role promotes best practices, leverages technology and data-driven solutions, and ensures the delivery of accurate, reliable, and meaningful financial information…
Added 12 hours ago
FO
Senior Director, Enterprise Technology Services
Federation of Canadian Municipalities
Ottawa, ON · Hybrid - Ottawa
- Full-time
Reporting to the Chief Operating Officer, the Senior Director, Enterprise Technology Services provides enterprise leadership for FCM's technology strategy, digital platforms, cybersecurity,…
Added 17 hours ago
LS
District Visual Language Interpreter
Langley School District #35
Langley (District), BC · Langley, BC
- Full-time
Under the direction of the LSS director, or designate, the District Visual Language interpreter aids and support students, staff, and families in the district. The Educational Interpreter…
Added 18 hours ago
SM
RQ00833 – Program Manager – Senior
S M Software Solutions Inc
Toronto, ON
- Full-time
…Ontario's (PHO) Public Health Data Utility (PHDU) and Immunization Information System (IIS) initiatives, coordinating multidisciplinary teams, vendors, and external partners to ensure…
Added 20 hours ago
AI
Strategic Sourcing Manager
American Iron & Metal (AIM)
Montreal, QC
- Full-time
Act as a strategic business partner to Finance, Operations, Information Technology, Human Resources, and other corporate functions.
Added 20 hours ago
IE
Manager, Supply Chain & Innovation
IMAX Enhanced | Streaming & Consumer Technology
Mississauga, ON
- Full-time
For more than 50 years, IMAX has been a global leader in entertainment technology, redefining how stories are experienced on the world’s biggest screens. Our mission is to power…
Added 20 hours ago
IE
Analyst, Business
IMAX Enhanced | Streaming & Consumer Technology
Mississauga, ON
- Full-time
IMAX is seeking a Business Analyst to bridge business functions, technology teams, data teams, project management, and senior leadership in defining and delivering technology-enabled…
Added 22 hours ago
SA
Operations Director
SAMSIC Assistance Canada Inc
Dorval, QC
- Full-time
For more information about our company, visit our websites at: www.samsic.aero or www.samsic.com
Added 22 hours ago
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Information Technology Operations Manager
Cardata
Canada
- $80,000 to $120,000 CAD / year
- Full-time
Partner with the Director of Engineering to implement and maintain IT security and controls to ensure that Cardata systems and information is secure and protected.
Added 22 hours ago
PT
Control Systems Engineer
ProSlide Technology
Ottawa, ON
- Full-time
…communication skills, with the ability to convey complex technical information to non-technical stakeholders.…

Redwood Software

Director, Customer Success Operations & Education

Toronto, ON, Canada

$150,000 to $170,000 CAD / year

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Job details

Pay: $150,000 to $170,000 CAD / year
Posting language: English
Posted: Oct 6, 2026

Original job description

OUR MISSION

At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.

ABOUT US

Redwood Software is the leading orchestration platform for the autonomous enterprise, driving business transformation at the lowest total cost of ownership. Redwood empowers organizations to intelligently automate and orchestrate mission-critical business and IT processes across complex ERP, hybrid cloud, data and emerging agentic AI systems. Through its SaaS-first automation fabric - with AI embedded across the automation lifecycle - Redwood accelerates the path to autonomous operations. Backed by 30 years of experience and trusted by more than 50% of the Fortune 50, Redwood helps organizations unlock human potential to focus on innovation, growth and what’s next.

CORE VALUES

One Team. One Redwood Make Your Own Weather Obsess over Customer Success Work the Problem Be Curious Own the Outcome Respect Each Other

YOUR IMPACT

As a Director, Customer Success Operations & Education you will be responsible for leading the operating strategy, infrastructure, and customer learning ecosystem supporting Redwood’s global Customer Success organization. You will define how Redwood scales consistent, data-driven customer experiences across the full customer lifecycle, while ensuring customers, partners, and internal teams have the knowledge and resources needed to maximize the value of Redwood’s software solutions.

Define and lead the global Customer Success operations strategy, roadmap, and governance model in alignment with Redwood’s customer and business objectives.
Design and continuously improve the customer lifecycle operating model across onboarding, adoption, value realization, risk management, customer feedback, renewals, and advocacy.
Establish scalable processes, service standards, playbooks, and engagement models that create consistent customer experiences across products, segments, and regions.
Partner with Customer Success leadership to improve capacity planning, resource allocation, account coverage, and organizational scalability.
Identify operational risks, process gaps, and areas of friction, and lead cross-functional initiatives to address them.
Establish governance mechanisms that drive accountability, consistency, and continuous improvement across the Customer Success organization.
Establish the Customer Success measurement framework and executive reporting strategy, connecting operational activity to customer and business outcomes.
Define and monitor KPIs across onboarding, time-to-value, product adoption, customer health, satisfaction, retention, education engagement, and operational efficiency.
Translate customer and operational data into actionable insights, recommendations, and investment priorities for senior leadership.
Partner with Finance, Sales Operations, and Customer Success leadership to strengthen forecasting, resource planning, and performance visibility.
Improve the quality, accessibility, and governance of customer data across systems and teams.
Own Redwood’s global customer education vision and multiyear strategy across products, customer segments, partners, and stages of the customer lifecycle.
Ensure education programs support faster onboarding, increased product adoption, stronger customer proficiency, and long-term value realization.
Oversee scalable learning experiences, including instructor-led training, digital learning, webinars, product documentation, video tutorials, learning paths, and certification programs.
Develop a role- and competency-based learning framework supporting customers from new users through advanced technical practitioners.
Evaluate opportunities to expand certification, partner enablement, and other scalable or revenue-generating education offerings.
Champion modern learning approaches, including AI-assisted content development, personalization, self-service learning, and learning automation.
Develop a structured Voice of the Customer program that captures, analyzes, and communicates customer insights across the organization.
Represent customer needs and operational priorities in product planning, go-to-market initiatives, and executive decision-making.
Partner with Product and Engineering to connect customer feedback, adoption data, and learning needs to product-roadmap decisions.
Collaborate with Professional Services, Support, Marketing, and Sales to create a cohesive customer journey and eliminate gaps between functions.
Build strong relationships with strategic customers and partners to understand evolving needs and validate program direction.
Present strategies, performance insights, risks, and recommendations to executive stakeholders.
Own the strategy, evaluation, implementation, adoption, and optimization of Customer Success and customer education technologies.
Lead the effective use of customer success platforms, learning management systems, analytics solutions, feedback platforms, and content-development tools.
Establish system governance, data standards, integrations, and workflows that improve team productivity and customer visibility.
Evaluate emerging technologies, including AI-enabled platforms, that can improve customer engagement, predictive insights, learning effectiveness, and operational scale.
Manage key technology vendors, contracts, budgets, and implementation partners.
Lead, develop, and scale a multidisciplinary team that may include Customer Success operations professionals, instructional designers, trainers, learning-program managers, and content creators.
Build an organizational structure and talent strategy that supports Redwood’s growth and evolving customer needs.
Coach and develop managers and individual contributors while establishing clear expectations, career paths, and succession plans.
Foster a culture of customer focus, accountability, innovation, collaboration, and continuous improvement.
Develop annual operating plans, budgets, staffing models, and investment recommendations for Customer Success Operations and Education.
Manage competing priorities across multiple strategic initiatives while maintaining strong execution and stakeholder alignment.
Drive measurable improvements in Customer Success operating-model adoption, customer-health visibility, onboarding and time-to-value, product adoption, customer proficiency, education outcomes, operational efficiency, customer feedback integration, satisfaction, retention, and long-term customer value.

YOUR EXPERIENCE

Bachelor’s degree in Business, Education, Instructional Design, Operations, Technology, or a related field; master’s degree preferred.
At least 10 years of progressive experience across Customer Success operations, customer education, enablement, training, instructional design, or related functions.
Five or more years of leadership experience, including leading managers, multidisciplinary teams, or globally distributed functions.
Demonstrated success defining and executing Customer Success operations or customer education strategies within a SaaS, enterprise software, or technology organization.
Proven ability to build scalable operating models, processes, programs, and systems that improve customer and business outcomes.
Experience partnering with executive leaders and influencing strategy across Customer Success, Product, Engineering, Sales, Marketing, Professional Services, Support, and Finance.
Strong understanding of the enterprise customer lifecycle, including onboarding, adoption, value realization, risk management, retention, and advocacy.
Experience establishing performance frameworks and using data to evaluate customer health, operational efficiency, learning effectiveness, and business impact.
Strong knowledge of learning management systems and digital learning platforms; experience with Skilljar preferred.
Experience selecting, implementing, or optimizing Customer Success platforms, customer-feedback systems, analytics tools, and content-authoring technologies.
Demonstrated ability to manage organizational change, complex cross-functional programs, budgets, vendors, and competing priorities.
Exceptional executive communication, stakeholder-management, and presentation skills.
Strong business judgment with the ability to move effectively between long-term strategy and operational execution.
Passion for simplifying complex technology and helping customers realize measurable value from enterprise software.
Experience supporting global enterprise customers across multiple products, regions, or customer segments preferred.
Background in automation, enterprise software, SaaS, ERP, or other technically complex product environments preferred.
Experience building customer certification, partner education, or scaled digital-learning programs preferred.
Familiarity with AI-enabled customer engagement, learning personalization, content development, or operational analytics preferred.
Track record of connecting education and Customer Success initiatives to improved adoption, time-to-value, retention, expansion, or customer satisfaction preferred.

Pay Transparency: The typical base salary range for this position is CAD $150,000 - $170,000 annually. The range represents base salary only, and does not include company bonus, incentive for sales roles, equity or benefits, as applicable. Final compensation will be determined based on the candidate's skills, experience, and relevant qualifications.

Vacancy Status: Existing vacancy

AI Transparency Disclosure: As part of our commitment to hiring transparency and in compliance with Ontario law, please be advised that we utilize artificial intelligence (AI) tools during our interview process. Specifically, we may use an AI-enabled notetaking assistant to help capture and summarize interview discussions. This tool is used solely to assist our hiring team in summarizing candidate information; all final hiring and selection decisions are made exclusively by individuals on the hiring team.

If you like growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us!

THE LEGAL BIT
Redwood is an equal opportunity employer. Redwood prohibits unlawful discrimination based on race, colour, religion, sex, gender identity, marital or veteran status, age, national origin, ancestry, citizenship, physical or mental disability, medical condition, genetic information or characteristics (or those of a family member), sexual orientation, pregnancy or any other consideration made unlawful by regional or local laws. We also prohibit discrimination based on a perception that anyone has any of those characteristics or is associated with a person who has or is perceived as having any of those characteristics. All such discrimination is unlawful and will have a zero tolerance policy applied to it.

Redwood will comply with all local data protection laws, including GDPR when it comes to the handling and processing of personal data. Should you wish for us to remove your personal data from our recruitment database, please email us directly at Privacy@Redwood.com

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More about this job

Responsibilities

You will lead the global operating strategy, infrastructure, and customer learning ecosystem to drive consistent, data-driven customer experiences. This role involves managing cross-functional teams to optimize the customer lifecycle, from onboarding and adoption to value realization and retention.

Requirements

The role requires at least 10 years of progressive experience in Customer Success operations or education, with at least 5 years in a leadership capacity. A bachelor's degree is required, with a preference for a master's degree and a background in SaaS or enterprise software environments.

Skills

Customer Success Operations
Customer Education
SaaS
Strategy Development
Data-driven Decision Making
Capacity Planning
Learning Management Systems
Instructional Design
Change Management
Stakeholder Management
Process Improvement
KPI Monitoring
Enterprise Software
Team Leadership
Budget Management
Cross-functional Collaboration

Visa sponsorship

Not detected in the job text

Keywords

Customer Success
Operations
Education
SaaS
Orchestration Platform
Automation
AI
Enterprise Software
Lifecycle Management
KPIs
Governance
Skilljar
Instructional Design
Change Management
Data Analytics
Forecasting
Resource Planning
Customer Health
Onboarding
Retention
Advocacy
Strategy
Leadership
Cross-functional
Budgeting
Vendor Management
Product Adoption
Time-to-value
Voice of the Customer
ERP

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