VP of Customer Success at CloudShare — Denver, CO

About Us

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 deliver demos, training, POCs, onboarding, and certifications through secure, scalable virtual environments.

We are looking for an experienced VP of Customer Success to lead our global Customer Success organization and help customers maximize the value of CloudShare throughout their lifecycle.

Reporting directly to the CEO, you will be responsible for driving customer retention, product adoption, expansion, customer satisfaction, and long-term customer success. The ideal candidate is both strategic and hands-on, with a strong background leading Customer Success teams in high-growth B2B SaaS environments.

Responsibilities

Own the overall Customer Success strategy and execution across onboarding, adoption, customer health, renewals, retention, and expansion. Lead, mentor, and develop a high-performing Customer Success organization, creating a culture of accountability, customer obsession, and continuous improvement. Drive Net Revenue Retention (NRR), Gross Revenue Retention (GRR), customer satisfaction, and overall customer outcomes. Build scalable customer success processes, playbooks, and operational frameworks that support continued company growth. Develop customer segmentation strategies, success plans, health scoring, and proactive engagement models. Partner closely with Sales, Product, Professional Services, Marketing, and Support to deliver a seamless customer experience throughout the customer lifecycle. Serve as the executive sponsor for strategic enterprise customers, building trusted relationships and supporting executive-level engagements. Establish and monitor key Customer Success KPIs, providing regular reporting and data-driven recommendations to executive leadership. Identify opportunities to improve customer adoption, reduce churn, and increase expansion opportunities. Build scalable forecasting and operational planning processes for renewals, customer health, and team capacity.

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. Familiarity with operational frameworks such as EOS, OKRs, or similar scaling methodologies. 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 Range: $175k–$200k annual base salary + 15-20% 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.