Senior Director, Customer Success

Assemble•Toronto, ON

38d•Hybrid

About The Position

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 [http://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.

Requirements

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

Nice To Haves

Experience working across membership, events, or sponsorship-driven environments is a strong asset

Responsibilities

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

Benefits

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

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