Director of Customer Success

CloudShare is a fast-growing, AI-first SaaS company delivering virtual hands-on labs that help organizations drive customer acquisition, product adoption, skill development, and retention through realistic software experiences.

Trusted by hundreds of enterprise organizations, CloudShare enables customers to create, deliver, manage, integrate, and measure secure and scalable software experiences across technical training, product demonstrations, proofs of concept, onboarding, enablement, certifications, and customer and partner education.

We are looking for an experienced Director of Customer Success to lead and scale our global Customer Success organization across an enterprise B2B SaaS customer base.

Reporting directly to the CEO, this leader will be responsible for driving customer adoption, measurable business outcomes, retention, renewals, expansion, customer satisfaction, and long-term success. You will build strong executive relationships, identify opportunities to expand CloudShare’s use across teams and use cases, and create a scalable Customer Success operating model.

The ideal candidate is a strategic, hands-on customer leader who can operate effectively at both the executive and operational levels. You understand how to translate technology capabilities into business outcomes and can build trusted relationships across technical, business, learning, enablement, and executive stakeholders.

Responsibilities

• Own and execute the Customer Success strategy and operating model across onboarding, adoption, customer health, renewals, retention, expansion, and advocacy.
• Lead, mentor, and develop a high-performing Customer Success team, creating a culture of accountability, customer obsession, collaboration, and continuous improvement.
• Establish clear customer objectives, success plans, adoption strategies, and measurable outcomes that demonstrate the business value of CloudShare.
• Drive Net Revenue Retention (NRR), Gross Revenue Retention (GRR), product adoption, customer satisfaction, time to value, and overall customer health.
• Build scalable Customer Success processes, playbooks, and operational rhythms across onboarding, implementation, business reviews, adoption, renewals, and executive engagement.
• Develop customer segmentation, coverage models, health scoring, and proactive engagement strategies to identify adoption risks and address potential churn or renewal concerns.
• Partner with Sales to support renewals and identify opportunities to expand CloudShare across customer teams, audiences, and use cases.
• Build trusted relationships with senior customer stakeholders and serve as an executive sponsor for strategic enterprise customers.
• Partner closely with Sales, Product, Professional Services, Marketing, Support, and Engineering to deliver a seamless customer experience and translate customer insights into actionable internal priorities.
• Establish Customer Success KPIs, forecasting, and operational planning processes, providing executive leadership with clear visibility into customer health, trends, risks, opportunities, and team capacity.
• Use technology, automation, AI, and data to scale Customer Success and support continued company growth.
• Develop a systematic customer advocacy program, identifying customers for references, speaking opportunities, case studies, and other proof points that demonstrate CloudShare’s value.

Requirements

• 6+ years of leadership experience in Customer Success, Customer Experience, Account Management, or related customer-facing SaaS leadership roles.
• Proven experience scaling high-growth SaaS companies, ideally from $10M-$50M ARR and beyond.
• Strong track record improving customer retention, adoption, expansion, and overall customer health.
• Deep understanding of SaaS business models, recurring revenue, customer lifecycle management, and success metrics.
• Experience working with enterprise customers and executive stakeholders.
• Strong analytical and operational mindset with the ability to use data to drive decisions.
• Excellent leadership, coaching, communication, and cross-functional collaboration skills.
• Hands-on leader who enjoys building processes while remaining close to customers and the business.
• Experience working closely with executive leadership and influencing company strategy through customer insights.

Nice to have

• Experience in customer education, learning technologies, virtual labs, cybersecurity, developer platforms, or technical enablement environments.
• Experience working with enterprise customers and customer success-driven SaaS organizations.

Benefits

We offer a competitive compensation package including:

• Medical, Dental, Vision benefits
• 401K
• Flexible PTO
• 12 Paid Holidays
• Hybrid work (3 days in office) with modern downtown Denver location
• Free Parking
• Onsite Gym

Compensation: $150k annual base salary + 10% bonus

Please note that CloudShare considers various factors in determining pay, including, but not limited to geographic location, qualifications, licensures, certifications, experience, and other skills relevant to the needs of the business.

• Comprehensive and market-competitive benefits.
• Complimentary onsite parking in downtown Denver
• Collaborative team atmosphere that values the contributions of all employees

CloudShare is proud to be an Equal Opportunity Employer. All qualified candidates will be considered without regard to race, color, religion, national origin, age, disability, sex, marital or familial status, status as a protected veteran, or any other characteristic protected by law.