Senior Director, Customer Success at Assemble – Toronto, Ontario

We’re Assemble—a company built to serve the many business leaders that struggle to make important decisions with certainty. We help enterprise leaders cut through the noise with trusted peer insights that bridge the gap between data overload and decision-making clarity. Our work has real impact, and our team is made up of smart, driven people who genuinely care about doing great work together.

Our unique approach leverages peer intelligence—a one-of-a-kind advantage created by convening the right people around the right questions—enabling leaders from top global companies to engage in meaningful discussions and gain actionable insights across diverse industries. From finance to manufacturing, Assemble empowers leaders to make confident, strategic decisions that accelerate progress and innovation.

Learn more about our brands:

• Executive Platforms (executiveplatforms.com) hosts summits that provide senior executives with a unique space to explore new ideas, innovations, and inspirations, fostering personal and professional growth.
• Board.org (board.org) offers unbiased peer insights from a trusted community—led by expert advisors—that help leaders and their teams at big companies quickly make informed strategic decisions.

This role is based at our Toronto HQ, right in the heart of downtown. We move fast, think big, and work hard—but we also have a lot of fun doing it. The energy in our office reflects our culture: ambitious, collaborative, and full of momentum. Whether we’re solving complex challenges, celebrating wins, or sharing a laugh, we show up because we want to—not because we have to. Learn more at www.theassemble.com.

How You’ll Contribute

You’ll be at the front line of our growth—connecting with senior decision-makers and bringing the right people to the table for powerful, peer-driven conversations.

The Senior Director of Customer Success will lead and scale a newly centralized, customer operations team responsible for delivering reliable, exceptional experiences across the three different customer types in the business, ultimately driving retention. This will require building processes that take the best of what’s working and deliver at scale. This role is both strategic and hands-on, with a strong focus on people leadership, revenue expansion (upsell/cross-sell), and operational excellence across membership, delegate, and sponsorship functions.

You will play a critical role in building a data-driven Customer Success organization that leverages systems, KPIs, and processes to deliver measurable impact, while fostering a collaborative and high-performance remote culture. It will also involve spotting opportunities cross-customers and coaching their team to do the same.

In this role, you will:

• Lead and develop a high-performing Customer Operations & Success team, providing coaching, mentorship, and clear performance management across both an in-person and remote environment
• Collaborate cross-functionally with Sales, Marketing, Product, and Finance to ensure alignment on customer goals and seamless handoffs – identifying areas for improvement and implementing meaningful, but miniminally disruptive change
• Act as a strategic voice of the customer, providing insights that influence business decisions and product/service improvements
• Standardize and improve processes across the customer journey to enhance experience, consistency, and operational efficiency
• Identify and execute growth opportunities within the existing customer base, building scalable playbooks for expansion
• Optimize systems and tools (CRM, customer success platforms) to ensure visibility, efficiency, and scalability of customer operations
• Own customer lifecycle strategy, providing reliable, exceptional service, boosting engagement, and driving revenue growth through upsell and cross-sell opportunities
• Establish and track key success metrics and KPIs (e.g., onboarding time, response times, NPS scores, retention rates, expansion revenue, customer health scores) across membership, delegate, and sponsorship teams
• Drive a data-first culture, leveraging dashboards and reporting to inform decisions and improve performance across teams
• Lead remote team operations, ensuring strong communication, accountability, and engagement across distributed team members

What Sets You Up for Success

You don’t need decades of experience to make a big impact here—just the mindset, motivation, and willingness to learn fast. You’ll thrive in this role if you bring:

• 5-8+ years of experience in Customer Operations or Customer Success leadership roles
• Strong operational mindset with experience improving processes, workflows, and systems – experience with project management tools (eg. Asana) a plus
• Proven experience leading and scaling high-performing teams, including remote or distributed teams
• Strong track record of driving customer retention across multiple customer segments simultaneously
• Deep experience building and managing KPIs, dashboards, and performance metrics
• Ability to ruthlessly prioritize the work that matters most, while keeping stakeholders in the know on progress and arming the teams with the tools to clearly see their priorities
• Experience optimizing and implementing CRM and customer success tools (e.g., Salesforce, HubSpot)
• Exceptional communication and stakeholder management skills, with the ability to influence cross-functional partners
• Experience working across membership, events, or sponsorship-driven environments is a strong asset

Why You’ll Love Working Here

We work hard, grow fast, and celebrate the wins along the way. At Assemble, you’ll be part of a collaborative team that values progress, people, and purpose. Here’s what you can expect:

• A competitive compensation package
• A hybrid work model that blends time in our downtown Toronto office with the flexibility of working from home
• A Flexible Paid Time Off Policy, 12 paid company holidays, and Summer Hours to help you recharge
• Comprehensive group benefits including health, dental vision, and flexible spending accounts to support your well-being
• Occasional opportunities to travel and experience our events in person
• Real room to grow your career in a high-growth environment where your contributions matter

Excited about this role, but don't meet 100% of the expected qualifications listed above? We'd still love for you to apply!

The Company is committed to building a diverse and inclusive workforce where unique experiences are valued, and everyone has the opportunity to contribute. Research has continuously shown that women and people of colour are less likely to apply to jobs unless they meet all of the listed qualifications. We want to help overcome this trend and seek to make space for unique and relevant skills and attributes. So, when applying to the Company, rest assured that your application is reviewed by a living, breathing human being and evaluated based on key competencies needed for success in the position. Our Recruiting team maintains awareness of all open roles which means your application may be assessed against multiple positions and we will reach out to gauge your interest in other opportunities as appropriate. Questions or concerns? Contact our HR Team, we'd be happy to connect!

As part of our commitment to creating an accessible and inclusive hiring process, we strive to provide reasonable accommodations for persons with medical conditions or disabilities that will enable their access to the hiring process. If you need an accommodation, please let us know the nature of your request.