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.

• 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.

• 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.

• Executive

• Full-time

• Other

• Software Development

We’re not displaying external referrals or job suggestions in this description. This listing reflects only the Head of Customer Success role at Penny Software.