Customer Success Manager

Laivly; Winnipeg; On-site; CAD 85,000 - 120,000; Full time

Job summary

Laivly is seeking a Customer Success Manager to oversee complex customer environments, understand what matters quickly, and translate ambitious ideas into measurable results. You will manage relationships with Enterprise and SME clients using Sidd, our AI-powered platform for transforming customer service operations.

You’ll be a strategic advisor and account leader, building trusted relationships with senior stakeholders, guiding both customers and internal teams from onboarding through

Qualifications

• Experience in strategic customer success or related roles.
• Exceptional communication with executives and stakeholders.
• Ability to structure ambiguous problems and drive decisions.
• Proactive, accountable, and data-driven mindset.

Responsibilities

• Own the full customer lifecycle from onboarding to renewal and expansion.
• Build trusted relationships with senior client stakeholders.
• Create account plans aligning priorities with measurable outcomes.
• Coordinate internal resources to remove adoption barriers and deliver value.
• Lead business reviews and communicate clearly across teams.

Skills

Strategic communication

Account management

Data-driven

B2B SaaS

Tools

APIs

AI tools

LLMs

Automation

Job description

About Laivly

Seeking curious and creative types! We are an ambitious company of innovators building and shaping the future of customer service technology. Our solutions help the world’s biggest brands leverage artificial intelligence, machine learning, and digital automation in their contact centers to deliver better customer experiences. Led by a team of established contact center experts, Laivly addresses the unique needs and challenges of customer service programs, with an emphasis on ethics in AI and the customer service agent experience.

This role is remote and open to all Canadian residents.

About the role

This is not a traditional Customer Success Role.

Laivly is looking for a Customer Success Manager who can walk into a complex customer environment, quickly understand what matters, and turn ambitious ideas into measurable results. You’ll own relationships with Enterprise and SME clients using Sidd, our AI-powered platform for transforming customer service operations.

You’ll be part strategic advisor, part account leader, and part operator. You’ll build trusted relationships with senior client stakeholders, bring structure to ambiguity, and keep customers moving from opportunity through implementation, adoption, renewal, and expansion. You’ll work closely with Technical Solutions, Product, and Engineering to solve difficult problems, while remaining accountable for the customer relationship and business outcome.

This role is for someone who prepares deeply, communicates exceptionally well, and develops an informed point of view instead of simply reporting status. Our strongest CSMs spot risks early, ask sharp questions, create momentum, and confidently guide both customers and internal teams toward the right outcome.

You’ll enjoy this role if you are curious, commercially minded, highly accountable, and energized by building inside a fast-moving AI company.

As CSM, you will:

• Own the overall customer lifecycle and account strategy, from onboarding through adoption, value realization, renewal, and expansion, partnering with deployment and technical teams during implementation
• Build trusted relationships with senior client stakeholders and become a credible advisor on how AI and automation can improve their operations
• Create account plans that connect customer priorities, solution delivery, measurable outcomes, risks, and growth opportunities
• Surface customer priorities, business requirements, and operational challenges, partnering with technical teams on detailed discovery, workflow mapping, and solution design
• Coordinate the right internal resources to address customer risks, remove barriers to adoption, and ensure issues are resolved with clear ownership and communication
• Bring structure and momentum to complex situations, ensuring decisions are made, commitments are clear, and open items are driven to completion
• Identify account risks before they become urgent and lead clear mitigation plans across client and internal stakeholders
• Act as the voice of the customer, providing structured feedback to product, engineering, and leadership
• Lead strategic and operational business reviews that demonstrate value, surface decisions, and establish accountability for next steps.
• Challenge customers and internal teams constructively when decisions or delays put the intended outcome at risk.
• Mentor and guide junior team members, helping to scale the CSM function at Laivly

As CSM, you have:

• You have 3-5+ years of experience in strategic customer success, consulting, solutions consulting, technical account management, product, or another complex client-facing role
• You are an exceptional communicator who can establish credibility with senior executives, operational leaders, and technical stakeholders
• You prepare thoroughly, ask thoughtful questions, and quickly develop an informed point of view
• You can take an ambiguous customer problem, create structure around it, and drive people toward a decision and plan
• You have strong commercial judgment and understand how customer outcomes connect to retention, expansion, and long-term account value
• You are proactive and highly accountable. You do not wait for someone else to identify the next step or chase you for an update
• You can manage strong personalities, navigate difficult conversations, and challenge stakeholders constructively
• You are analytically minded and comfortable using data to assess results, identify risks, and recommend action
• You are technically curious and comfortable learning how APIs, AI tools, LLMs, and automation products work
• You are energized by startup environments where priorities move quickly and the playbook is still being built
• Experience in B2B SaaS, AI and automation, contact centres, or digital transformation is an asset

Life at Laivly

Laivly gives you the opportunity to collaborate and grow your career with a creative, diverse, and passionate team. We work hard and play often, with a flexible environment that works with you. A career at Laivly means being part of a fun-loving, dedicated team of creatives, risk takers and game changers. It’s about sharing your talent and imagination to develop innovative tech that’s revolutionizing the way top brands interact with the world.

We’ve got a shared mission—and a Laivly future. Join us today!

Laivly provides Equal Employment Opportunities in accordance with all provincial and federal laws. Laivly is committed to ensuring equality of opportunity in all aspects of employment and does not discriminate based on protected characteristics.

Laivly is committed to accommodating persons with disabilities. If you need accommodation at any stage of the application process or want more information on our accommodation policies, please let us know.