Senior Director, Customer Success

Senior Director, Customer Success Rapid7 is seeking a Senior Director of Customer Success to lead the care, retention, and growth of a significant portion of our annual recurring revenue. In this strategic leadership role, you will design and execute a customer relationship strategy focused on driving high retention across a highly diverse customer base. You will lead a high-performing team of Customer Success Managers, translating customer insights into scalable methodologies that deliver consultative, team-based strategic guidance. About the Team The Customer Success team is responsible for the care, retention, and growth of Rapid7’s diverse customer base, ranging from SMBs to Fortune 1000 organizations. Reporting to the VP of Customer Success, the team focuses on driving product adoption and delivering measurable impact through a culture of accountability and continuous improvement. We partner closely with Sales, Product, Marketing, and Operations to ensure customer-centric execution and support long-term revenue growth. About the Role The Senior Director of Customer Success will lead a team of managers and senior CSMs to own and drive key performance indicators, including gross and net revenue retention. You will act as a strong internal voice for the customer, establishing proactive risk frameworks and implementing scalable infrastructure to support sustainable team and revenue growth. In this role, you will: Own Strategic Outcomes: Drive key performance indicators including risk identification, activity management, product adoption, and gross/net revenue retention. Lead and Develop Talent: Recruit, coach, and motivate a high-performing team, building a customer-focused culture rooted in accountability and measurable impact. Establish Operational Rigor: Implement scalable processes, dashboards, and reporting cadences to support data-driven decision-making and sustainable growth. Drive Cross-Functional Alignment: Partner with Sales, Product, and Support to influence process improvements and collaborate on expansion strategies based on customer insights. Manage High-Level Escalations: Provide hands-on leadership in complex account scenarios, modeling executive presence during high-level negotiations alongside direct reports. Scale Methodologies: Develop repeatable, consultative methodologies that enable CSMs to deeply understand and deliver on customer objectives. The skills you’ll bring include: Proven Leadership: A minimum of 10-15 years of experience in B2B client-facing roles with at least 5+ years specifically leading and developing managers or senior-level CSMs. Metric-Driven Success: A proven track record of owning and driving retention, expansion, and adoption metrics within large Customer Success organizations. Executive Presence: Strong experience handling complex commercial negotiations and high-level customer escalations. Operational Expertise: Demonstrated ability to design scalable lifecycle frameworks and leverage CRM/CSM platforms to inform strategy. Stakeholder Management: Excellent cross-functional collaboration skills with the ability to influence internal partners and advocate for customer needs. Adaptability and Travel: Ability to travel up to 20% of the time for customer meetings or remote office visits. We know that the best ideas and solutions come from multi-dimensional teams. That’s because these teams reflect a variety of backgrounds and professional experiences. If you are excited about this role and feel your experience can make an impact, please don’t be shy - apply today. #LI-CG4 #LI-Remote About Rapid7 At Rapid7, our vision is to create a secure digital world for our customers, our industry, and our communities. We do this by harnessing our collective expertise and passion to challenge what’s possible and drive extraordinary impact. We’re building a dynamic and collaborative workplace where new ideas are welcome. Protecting 11,500+ customers against bad actors and threats means we’re continuing to push the envelope just like we’ ve been doing for the past 20 years. If you ’re ready to solve some of the toughest challenges in cybersecurity, we’re ready to help you take command of your career. Join us. Rapid7, Inc. is committed to fair and equitable compensation practices. A candidate’s salary is determined by various factors including, but not limited to, relevant work experience, skills, and certifications. We evaluate compensation decisions on a case-by-case basis, and it is not typical for an individual to be hired at the very top of the salary range. The salary range for this role in the US is: $189,600.00 - 256,500.00 USD Annual Salary ranges may vary based on geographical location. This range does not include variable/incentive compensation, equity and benefits (where applicable/eligible). All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, age, national origin, disability, protected veteran status or any other status protected by applicable national, federal, state or local law.