Senior Director of Customer Success

iManage•Chicago, IL

3d•$225,000 - $275,000•Hybrid

About The Position

We offer a flexible working policy that supports a healthy balance between personal and professional well-being. This role requires in-office presence on Tuesdays & Thursdays to collaborate, connect, and learn from peers - while also maintaining the flexibility for meaningful work-life balance. Being a Senior Director, Customer Success at iManage Means… You will lead our Americas team dedicated to ensuring our customers achieve their desired outcomes while growing their relationship with iManage. You will own customer retention, adoption, and advocacy across a high-impact portfolio, leveraging your ability to inspire teams, build trust with executives, and drive meaningful business impact across the organization.

Requirements

10+ years of customer success, account management, or customer-facing leadership experience in a B2B SaaS environment, with proven track record managing strategic customer portfolios.
A demonstrated ability to develop, mentor, and lead high-performing teams through clear goal-setting, performance feedback, and coaching that builds confidence and promotes growth.
Proven expertise in designing and executing customer retention, adoption, and engagement strategies that measurably improve customer outcomes and reduce churn.
Strong executive presence and stakeholder management skills with the ability to build trust with C-level customers, influence cross-functional teams, and drive alignment across organizations.
Demonstrated emotional intelligence with the ability to listen actively, understand diverse perspectives, and lead with empathy while maintaining high standards for accountability and results.
Strong business acumen with deep understanding of SaaS metrics (retention, churn, net revenue retention), financial impact of customer decisions, and ability to connect customer outcomes to company strategy.
A proven ability to identify and escalate customer risks, develop mitigation strategies, and communicate transparently with internal and external stakeholders.
Experience conducting and facilitating complex customer conversations including executive business reviews, health assessments, and success planning sessions.

Nice To Haves

Legal and corporate/finance industry knowledge or experience selling/supporting into these verticals.
A working knowledge of iManage products and solutions, particularly iManage Work, Drive, Tracker, and Insight+.
Hands-on experience with customer success tools such as Salesforce, or ticketing systems for managing customer interactions and outcomes.
Project Management Professional (PMP) or ITIL certification.
Experience implementing enterprise cloud and/or security platform solutions with complex customer bases.
Demonstrated ability to work effectively both independently and as a collaborative member of a distributed, global team.

Responsibilities

Leading and developing a team of customer success professionals to manage strategic customer portfolios while driving accountability for key retention, adoption, and satisfaction metrics; establishing data-driven performance targets aligned to company OKRs and regularly analyzing team performance against targets.
Developing and mentoring direct reports to think strategically and analytically; providing regular performance feedback aligned to the iThrive framework; fostering a culture of data-driven decision making and continuous learning through coaching and development opportunities.
Leveraging predictive analytics and customer health scoring models to identify at-risk accounts, churn signals, and expansion opportunities; translating data insights into proactive mitigation and growth strategies that demonstrably reduce churn and increase net revenue retention.
Conducting regular customer health assessments through direct conversations combined with rigorous data analysis of usage patterns, feature adoption, support ticket trends, and business outcomes; synthesizing insights to prioritize organizational resources and inform product strategy.
Establishing executive-level customer relationships by conducting Executive Business Calls and Quarterly Business Reviews grounded in data analysis, customer metrics, and competitive positioning; using insights to guide strategic account planning and align customer outcomes with iManage roadmap.
Developing and executing evidence-based customer adoption, loyalty, communication, and engagement strategies informed by customer behavior data, industry benchmarks, and competitive intelligence; measuring strategy effectiveness through defined KPIs and iterate based on results.
Designing and implementing strategic customer success programs and enablement content that are informed by customer segmentation analysis, adoption maturity benchmarks, and outcome data; continuously optimizing programs based on performance metrics and customer feedback.
Coordinating cross-functional initiatives with sales, support, product management, and professional services; using data to identify customer obstacles and barriers to adoption, recommending solutions, and tracking impact on customer outcomes and retention.
Building and maintaining strong internal partnerships with colleagues in sales, channel, support, product management, and partner enablement; establishing shared data dashboards and reporting to align on customer priorities and cultivate cooperation in customer activities.

Benefits

Flexible working policy
Health/Vision/Dental/Life Insurance
401k Retirement Savings Plan with a company match up to 4%
Enhanced leave for expecting parents (20 weeks 100% paid for primary leave, and 10 weeks 100% paid for secondary leave)
Flexible time off policy
Company wellness days
Access to RethinkCare, a global behavioral health platform
Annual performance-based bonus
Unlimited access to LinkedIn Learning courses and interactive Microsoft courses & training
Internal development framework for career path ownership