Head of Customer Success Manager

Overview Head of Customer Success

at

Penny Software

– we are seeking an experienced and strategic leader to head our customer success function, drive long-term value for customers, oversee the team, define success metrics, and ensure customers achieve maximum value from our solutions while driving retention, growth, and advocacy. The ideal candidate combines a customer-first mindset with strong leadership, operational excellence, and proven experience in scaling customer success for a SaaS or B2B company.

Responsibilities

Develop and execute the overall customer success strategy aligned with company goals.

Lead, mentor, and grow a high-performing team of Customer Success Managers and Account Managers.

Establish clear success metrics, KPIs, and reporting frameworks for customer retention, expansion, and satisfaction.

Serve as the executive sponsor for strategic customer accounts and escalate as needed.

Ensure a seamless onboarding, adoption, and renewal process across all customer segments.

Build strong, trusted advisor relationships with customer executives to ensure business outcomes are achieved.

Standardize customer success playbooks, workflows, and best practices.

Partner with Product, Sales, and Marketing to ensure customer needs are represented in roadmap and strategy.

Implement tools and processes for customer health scoring, lifecycle management, and proactive engagement.

Own customer retention and expansion metrics (churn, renewal, upsell, and cross-sell).

Collaborate with Sales on expansion opportunities and renewal negotiations.

Monitor customer health indicators and proactively address risks to prevent churn.

Qualifications

8-12 years of experience in Customer Success, Account Management, or related roles in B2B enterprise SaaS.

At least 3-5 years of leadership experience managing customer-facing teams.

Strong understanding of customer success frameworks, lifecycle management, and revenue impact.

Strong understanding of business flows, business analysis, and process optimization.

Proven track record of reducing churn and driving account growth.

Exceptional communication and executive presence with the ability to influence at all levels.

Data-driven with the ability to translate insights into actionable strategies.

Bachelors degree in Business, Management, or related field; MBA is a plus.

Seniority level

Executive

Employment type

Full-time

Job function

Other

Industries

Software Development

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