Head of Customer Success

Planned; Toronto; On-site; CAD 110,000 - 145,000; Full time

Job summary

A leading event management platform in Toronto is seeking a Head of Customer Success to elevate client interactions and ensure operational excellence. This role involves overseeing a large team, unifying processes, and leveraging data to enhance user experiences. The successful candidate will work closely with product teams and refine metrics that reflect client health. The company offers a competitive compensation package, unlimited PTO, and a collaborative, in-office environment.

Benefits

Unlimited PTO

Competitive total compensation package

Health, dental, vision insurance

Bus pass subsidy or indoor parking

Stocked snack bar & lunches in office 2x per week

Dog-friendly office

Relocation assistance, if needed

Qualifications

• Experience leading or scaling a customer success organization at a fast‑growing SaaS startup.
• A track record of building or optimizing CS functions from the ground up; process, metrics, culture, and team development.
• Demonstrated ability to use data and systems to scale onboarding operations, improve team efficiency, and forecast key business outcomes.
• Strong partnership with product teams, with an ability to influence and build roadmaps and improve user journeys.
• Proven people leader with a passion for hiring, developing, and retaining top talent.
• Comfort operating in ambiguity - you create clarity, not wait for it.

Responsibilities

• Oversee a team of ~20 across multiple client pods, driving alignment, clarity, and shared goals.
• Build consistent processes and standards so every client experience feels equally exceptional.
• Gather data and feedback from clients and internal teams, then translate that into actionable strategies that improve satisfaction, retention, and engagement.
• Be the voice of the customer in product discussions, helping to build the right features faster.
• Define and drive performance across NRR, CSAT, SLAs, and KPIs that reflect client health.
• Build a high‑performing, curious team that operates with ownership and accountability.

Skills

Leadership

Data analysis

Customer success management

Process optimization

User experience enhancement

Team development

Influencing product roadmap

Job description

Head of Customer Success

Montreal, Quebec - Customer Success - In office - Full-time

Planned is an event management platform that helps companies streamline their meetings and events booking process. We make it easy for anyone to plan successful events while giving finance teams the visibility and control they need to maximize their budget. We already work with over 200 companies across North America - including PwC, L’Oréal, and Nike - and we’re on a mission to change the way organizations connect, collaborate, and celebrate.

We’re a fast‑growing, product‑driven Series B startup backed by top‑tier investors and powered by a team of builders who are obsessed with making a real impact.

We’re looking for a Head of Customer Success to lead the next evolution of how we serve our clients, from onboarding to renewal. This person will bring consistency, harmony, and excellence across our customer success organization, ensuring that every client interaction delivers real value and delight.

You’ll report directly to our CEO and work closely with Product and Revenue leadership to align our customer experience with our business and product strategy. Your mission will be to shape how we think about user experience, operational excellence, and long‑term client partnerships at scale.

What You’ll Do

Lead and elevate the CS function :

Oversee a team of ~20 across multiple client pods, driving alignment, clarity, and shared goals.

Unify how we work :

Build consistent processes and standards so every client experience feels equally exceptional.

Champion user experience :

Start by immersing yourself in our product and clients - shadowing the team, planning events with users, and understanding what works (and what doesn’t) before implementing change.

Turn insights into strategy :

Gather data and feedback from clients and internal teams, then translate that into actionable strategies that improve satisfaction, retention, and engagement.

Partner with Product :

Be the voice of the customer in product discussions, helping us build the right things, faster.

Own the metrics that matter :

Define and drive performance across NRR, CSAT, SLAs, and the KPIs that best reflect client health.

Coach and inspire :

Build a high‑performing, curious team that operates with ownership and accountability.

What You Bring

Experience leading or scaling a customer success organization at a fast‑growing SaaS startup.

A track record of building or optimizing CS functions from the ground up; process, metrics, culture, and team development.

Demonstrated ability to use data and systems to scale onboarding operations, improve team efficiency, and forecast key business outcomes.

Strong partnership with product teams, with an ability to influence and build roadmaps and improve user journeys.

Proven people leader with a passion for hiring, developing, and retaining top talent.

Comfort operating in ambiguity - you create clarity, not wait for it.

What We Offer

The space to lead, experience, and make decisions that move the needle - you’ll have the ability to completely reshape user experience and product.

Culture of high performance, strong talent density and in‑person collaboration.

Unlimited PTO.

Competitive total comp package.

All the tools and gear you need to be successful (Macbook, screens, mouse, keyboard, ChatGPT, etc.).

Health, dental, vision insurance.

Bus pass subsidy or indoor parking.

Stocked up snack bar & lunches in office 2x per week.

Dog‑friendly office.

Relocation assistance, if needed.

More About Planned

Read about our Series B raise.

Read up on our USP - being one vendor of record.

Here’s how we’re using AI.