Director, Customer Success

  • Full-time

Company Description

insightsoftware is a global provider of reporting, analytics, and performance management solutions that unlock the potential of business data and transform the way finance and data teams operate. We empower leaders from over 32,000 organizations to make timely and intelligent decisions. Our comprehensive solutions span Financial Planning and Analysis (FP&A), Controllership, and Data and Analytics. We deliver finance teams the insights required to navigate any economic climate and drive greater financial intelligence, while increasing productivity, visibility, accuracy, and compliance. Learn more at

Job Description

  • Partner with the General Managers and Product owners to drive overall retention and meet or exceed the defined retention goals.
  • Conduct detailed analysis of the customer base to identify leading indicators for churn and expansion.
  • Define and execute uplift strategies to optimize available price increases while minimizing customer churn.
  • Build predictive models for maximizing customer retention including actively influencing product roadmap, services/support delivery, billing and collections improvements.
  • Lead your team to deliver outstanding experiences that drive strong customer retention, expansion, adoption, and referrals.
  • Organize and lead a retention forecasting process– ensuring the execution of timely renewals including risk management with best case and worst case forecasting scenarios.
  • Increase customer lifetime value through success plans, customer satisfaction, and overall health scores.
  • Master retention performance reporting to develop data-driven insights on customer behavior.
  • Possess and display professional presence and credibility to function effectively both internally as well as at the highest level of customer contacts.
  • Strategically balances customer needs with business goals.
  • Drive a proactive NPS, at risk program, and other initiatives and measures to prevent customer attrition.
  • Build effective processes and systems to scale customer negotiations around renewals while ensuring product retention targets are met.
  • Manage a diverse set of renewal motions - spanning named accounts covered by CSMs, low touch uncovered accounts, partners, and self service customers.
  • Drive a standardized, proactive outreach and reactive interventions for various points in the journey by identifying opportunities to encourage feedback loops and continuous improvement.
  • Partner with peers to scale processes in on boarding, training, success management, support, and customer advocacy.
  • Increase opportunities for expansion and up-sells by creating a bridge between Account Management, Direct Sales, Channel Sales, Professional Services, and Customer Success teams.
  • Develop and share metrics to measure the effectiveness of Customer Success in meeting company and team goals.
  • Track, analyze, and report on Customer Success metrics across the organization.
  • Be a customer champion internally.

Achievements/Goals *Must Display in the 1st 6 months:

  • Work Ethic – operate in a fast-paced environment with a focus on achieving results.
  • Engaging/Executive Presence – quickly establish rapport and build relationships with partners and communicate successfully with clients. Ability to elevate and lead the conversation with Sr Executive from insightsoftware and our customers.
  • Teamwork – work cross-functionally to achieve team and individual goals.
  • Communication – communicate effectively with customers and internal cross-functional partners, creating promoters at every touch point.


  • 7+ years of management experience in customer success – including direct experience as a 2nd level manager for more than 1 year.
  • Experience integrating acquired companies and teams into success model
  • Experience with retention forecasting and management of a monthly process with a track record for accuracy and overachievement
  • Experience segmenting customers, providing different levels of outreach, from tech touch to personalized interaction
  • Experience in both on-prem and cloud-based success models
  • Strong communication and presentation skills, both verbal and written
  • Bachelor’s Degree in related field or equivalent experience
  • Experience in technical or commercial management of software support services, software development, or customer care around IT/Application services is highly preferred
  • Ability to travel up to 25%

Additional Information

Candidate will be required to visit our Toronto/Vancouver office based on support needs.  

All your information will be kept confidential according to EEO guidelines.


** At this time insightsoftware is not able to offer sponsorship to candidates who are not eligible to work in the country where the position is located. **

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Background checks are required for employment with insightsoftware, where permitted by country, state/province.

At insightsoftware, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace.