Job Overview
Location
Remote (United States)
Job Type
Full-time
Category
Operations
Date Posted
May 14, 2026
Full Job Description
đź“‹ Description
- • As a Manager, Customer Experience Operations at Tailscale, you will serve as the operational backbone of the global post-sales organization, ensuring Customer Success, Customer Success Engineering, and Support Engineering teams operate at scale to deliver exceptional customer outcomes.
- • You will own the operational rhythm of the Customer Experience organization, including reporting cadences, QBRs, renewal forecasting, health scoring, capacity modeling, and tooling, while designing and implementing customer journey strategies and automated workflows to process renewals and customer programs at scale.
- • You will partner with post-sales leadership, Revenue Operations, Finance, and Product to define customer segmentation, coverage models, and engagement strategies, align post-sales motions with company goals like NRR and GRR, and build dashboards that translate data into proactive recommendations on customer health, churn risk, and team performance.
- • You will develop and operationalize lifecycle programs and playbooks across onboarding, success plans, risk mitigation, escalations, expansion, and renewals, act as the primary point of contact for post-sales tooling (Salesforce, CS platform, BI reporting), and improve handoffs between Sales, CS, Support, and Engineering to ensure a seamless customer experience.
🎯 Requirements
- • 5 to 8+ years of experience in Customer Success Operations, Revenue Operations, or a related GTM operations role, preferably in a high-growth B2B SaaS environment.
- • Strong working knowledge of Salesforce (required) and a CS platform such as Gainsight, Planhat, or Totango.
- • Proficiency with BI and analytics tools such as Looker, with the ability to build reports and dashboards independently.
- • Familiarity with SQL or BigQuery is a strong plus; data fluency is essential.
- • Systems thinker who can connect workflows across CS, CSE, Support, and Revenue teams with strong analytical skills and the ability to build and interpret complex data, identify key insights, and communicate them clearly.
🏖️ Benefits
- • Competitive total compensation package including base salary, equity incentive plan, and variable commission (for quota-based roles).
- • Comprehensive group benefits with no waiting period, covering health, vision, dental, and more for you and your family.
- • Remote-first company culture with flexibility to work from anywhere with wifi, plus access to corporate co-working programs (e.g., WeWork) and intentional in-person connection through annual retreats and team off-sites.
- • $1,500 USD annual professional development stipend, plus mentorship, coaching, and internal promotion opportunities.
- • Generous parental leave program from day one, with top-ups for up to 26 weeks, and a build-your-own home office setup including company-owned laptop, monthly internet reimbursement, and $1,000 USD to customize your workstation.
Skills & Technologies
About Tailscale Inc.
Tailscale Inc. provides a zero-config virtual private network built on the open-source WireGuard protocol. It creates secure, encrypted mesh networks that connect devices, servers and users without traditional VPN hardware or complex firewall rules. The software runs on Linux, macOS, Windows, iOS, Android and container platforms, integrating with identity providers like Google Workspace, Microsoft Entra ID and Okta. Organizations use Tailscale to enable remote access to internal applications, SSH, RDP, databases and development environments, while maintaining centralized access controls and audit logs. The company is privately held and headquartered in Toronto, Canada.
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