Senior Manager / Associate Director, Customer Success (Canada Remote)
Dooly
Sales & Business Development, Customer Service
USD 155k-175k / year
Posted on Sep 13, 2025
Who we are:
Mediafly is the leading revenue enablement platform market-facing teams use to plan, predict, coach, and engage at the highest levels. Our unified suite of solutions create immersive buyer experiences; enable sellers to lead with value, allow managers to scale coaching, and empower leaders to forecast with confidence. In today’s unpredictable market, Mediafly is the key to delivering predictable efficient growth.
The Opportunity:
We are seeking a highly motivated and experienced Senior Manager or Associate Director of Customer Success to join our growing team. This role is ideal for a seasoned customer success professional who is passionate about leading and developing a team, driving customer adoption and retention, and contributing to the strategic direction of our Customer Success organization. You will be responsible for overseeing a portfolio of key customer accounts, guiding a team of Customer Success Managers (CSMs), and collaborating cross-functionally to ensure our customers achieve their desired outcomes with Mediafly.
What You'll Do:
- Lead and Mentor: Lead, coach, and develop a team of Customer Success Managers, fostering a culture of continuous learning, accountability, and excellence
- Drive Revenue: Collaborate with Renewal Managers to ensure revenue retention forecast accuracy and showcase customer ROI. Enable CSMs to identify and qualify upsell and cross-sell opportunities, working alongside the sales team to finalize these deals.
- Performance Management: Set clear performance goals, conduct regular performance reviews, provide constructive feedback, and implement performance improvement plans when necessary.
- Drive Success Metrics: Develop and execute strategies to improve key customer success metrics, including adoption, engagement, and retention rates.
- Cross-Functional Collaboration: Partner closely with sales, product, services, and support teams to ensure a seamless customer journey and drive product innovation.
- Process Improvement: Identify and implement improvements to our customer success processes and playbooks, enhancing efficiency and effectiveness.
- Thought Leadership: Stay informed on industry best practices and trends in customer success, contributing to the overall strategic direction of the department.
- Team Morale and Engagement: Foster a positive and collaborative team environment, promote knowledge sharing, and recognize achievements to maintain high morale and engagement.
- Customer Journey Optimization: Continuously analyze and optimize the customer journey from onboarding to renewal, identifying pain points and implementing improvements.
- Escalation Management: Acting as a primary point of escalation for complex customer issues, working cross-functionally to ensure timely and effective resolution.
- Customer Advocacy: Act as a key advocate for our customers, ensuring their feedback is heard and incorporated into our product roadmap and service offerings.
What You'll Bring:
- 5+ years of experience in Customer Success, with at least 2 years in a leadership or management role, preferably within a B2B SaaS environment.
- Proven ability to lead, mentor, and motivate a team of customer success professionals.
- Deep understanding of customer success principles and a strong passion for delivering exceptional customer experiences.
- Ability to develop and execute strategic plans that align with overall business objectives.
- Excellent written and verbal communication skills, with the ability to effectively communicate with customers, internal stakeholders, and senior leadership.
- Strong analytical and creative problem-solving skills, with the ability to identify and resolve complex customer issues.
- Ability to thrive in a fast-paced, dynamic, and evolving environment.
- Comfort with technology and the ability to quickly learn new software platforms.
- Bachelor's degree in a relevant field (Business, Marketing, Communications, etc.) or equivalent practical experience.
Nice-to-Have:
- Experience with a CRM platform (e.g., Salesforce) and Customer Success platforms (e.g., Gainsight).
- Experience in a sales enablement, content management, or revenue intelligence related industry.
$155,000 - $175,000 a year
Location and Work Setup
This is a 100% remote position with a collaborative team that values flexibility and trust. We use modern communication and collaboration tools to stay connected and productive across time zones.
Ready to make an impact on a product that matters? Apply today and help us build the next generation of our platform!
Why Mediafly?
Remote based
Flexible working hours
Generous Paid Time Off
Competitive Salary
Health Benefits
Transparent Career Paths
Generous Paid Parental Leave
Remote Stipend
Mediafly is an equal opportunity employer, which means we do not discriminate on the basis of race, color, religion, marital status, age, national origin, ancestry, physical or mental disability, medical condition, pregnancy, genetic information, gender, sexual orientation, gender identity or expression. We celebrate diversity and are committed to creating an inclusive environment for all employees. We welcome people of different backgrounds, experiences, abilities and perspectives and encourage all interested individuals to apply.
Thanks to our commitment to employee experience, Mediafly has been recognized as a Best Place to Work from Crain's, Inc. and BuiltIn.
Mediafly's HQ is based in Chicago, IL.
