Director of Customer Success Operations

About Us:

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 insightsoftware.com.

Job Description:

The Director of Retention Operations for the Reporting business unit is a strategic operations leader responsible for gross retention rate (GRR) and net retention rate (NRR) across a high-volume customer base. Reporting to the General Manager, this role consolidates customer success signal at scale, identifies churn risk and expansion opportunities across cohorts, and ensures execution of programmatic retention and growth strategies.

This is an internal, cross-functional operations role that brings discipline and scalability to retention by maintaining visibility into cohort and segment health trends, analyzing churn patterns and root causes, and ensuring that retention and expansion strategies are being executed with consistency and rigor.

Key Responsibilities

• Consolidate customer health signals (usage trends, engagement, support incidents, expansion opportunity) from customer success teams to provide the GM with weekly visibility into account and cohort health

• Track gross retention rate (GRR) and net retention rate (NRR) by product, segment, and cohort; conduct variance analysis to identify deterioration trends and positive momentum

• Identify at-risk account cohorts and customers; work with customer success to develop targeted interventions and track remediation progress

• Conduct root-cause analysis on churn trends; identify systemic issues (product, onboarding, support, pricing) and recommend operational or product improvements

• Partner with customer success, product, and marketing to design and implement retention and expansion plays (e.g., programmatic outreach, upgrade campaigns, engagement initiatives)

• Maintain dashboards that track GRR, NRR, churn cohorts, expansion opportunity, and other key retention metrics; provide predictive forecasts of end-of-period performance

• Work with customer success to develop and implement escalation and resolution protocols for at-risk accounts

• Provide regular reporting to the GM on retention performance, key drivers, and recommended actions

• Deep understanding of the at risk accounts and the plan of attack to maintain each customer and grow GRR.

• Identify and work to resolve issues impacting customer retention through process improvement challenges with renewal management and other CS ops related patterns.

What Success Looks Like

• The Director has real-time visibility into GRR and NRR performance by segment and cohort, with clear understanding of primary churn drivers

• At-risk cohorts are identified early (at least one quarter in advance), with documented interventions tracked to completion

• Churn analysis is conducted systematically for all at-risk accounts; patterns are identified and communicated to product and operations

• Retention and expansion plays are tracked against execution and adoption targets

• GRR and NRR meet or exceed target, with measurable improvement in efficiency and speed of intervention

Required Skills & Experience

• Seven to ten years of experience in customer success operations, retention analytics, or similar role in a high-volume B2B SaaS environment

• Deep understanding of SaaS metrics (GRR, NRR, CAC payback, churn drivers, cohort analysis) and ability to identify and investigate performance variances

• Demonstrable experience working with programmatic or high-volume customer bases (100 plus accounts or more)

• Strong analytical and data visualization skills; comfort with SQL, BI tools, and statistical analysis

• Experience designing and tracking retention initiatives or campaigns at scale

• Excellent communication skills and ability to distill complex analyses into actionable insights for leadership

• Project management mindset: ability to manage multiple retention and expansion initiatives in parallel

Core Attributes

• Systematic: Brings structure and process to high-volume environments; thinks in terms of cohorts and patterns, not just individual accounts.

• Analytical: Comfortable working with large datasets; good at identifying signal in noise.

• Collaborative: Partners well with customer success, product, and marketing; sees retention as a shared responsibility.

• Execution-oriented: Focuses on results and impact; isn't satisfied until strategies are tested, tracked, and optimized.

Compensation & Benefits

• Base salary: Competitive, based on experience. Bonus structure: 80 percent base, 20 percent bonus tied to GRR and NRR targets for the Reporting cohort.

• Benefits package includes health insurance, 401(k), professional development support, and flexible work arrangements.

The salary range in United States of America for this position is 160,000.00 to 201,000.00 USD Annual.

For sales roles, this range includes the commission target. For non-sales roles, this is a base salary only range; additional bonus eligibility may apply.

Your specific offer within this range will be determined by your skills, experience, and qualifications.

We are committed to pay transparency and fair compensation practices. If you have questions about our compensation approach, please don't hesitate to ask during the interview process.

Additional Information

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

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