Job Overview
Location
Remote (Canada)
Job Type
Full-time
Category
HR & Recruiting
Date Posted
May 14, 2026
Full Job Description
đź“‹ Description
- • Manager, Customer Experience Operations at Tailscale Inc. is a high-impact, cross-functional role that serves as the operational backbone of the global post-sales organization, ensuring scalable systems, data integrity, and strategic alignment to drive customer retention, expansion, and world-class experiences.
- • Day to day, the role involves owning the operational rhythm of the Customer Experience organization—managing reporting cadences, QBRs, renewal forecasting, health scoring, capacity modeling, and tooling—while designing customer journeys, implementing health scoring models, automating renewal workflows, and maintaining data integrity across Salesforce, CS platforms, and BI tools.
- • The role sits within Tailscale’s Revenue Operations team, partnering closely with Customer Success, Customer Success Engineering, Support Engineering, Finance, Product, and Marketing to align post-sales motions with company goals like NRR, GRR, product adoption, and support SLAs in a fully remote, high-growth B2B SaaS environment backed by top-tier investors.
- • The person in this role will learn to build and scale post-sales operations from the ground up, gain deep expertise in SaaS GTM motions, influence strategic decisions through data-driven insights, and directly impact customer health, retention, and expansion outcomes while developing leadership in cross-functional influence and systems thinking.
🎯 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.
- • Proven ability to lead strategic initiatives while executing hands-on in a fast-paced, evolving environment.
- • Highly collaborative with strong stakeholder management skills and the ability to influence without authority.
🏖️ Benefits
- • An inclusive, flexible environment where you can be your authentic self.
- • A 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 support for virtual and in-person social events and corporate co-working program access (e.g., WeWork).
- • $1,500 USD annually for professional development, plus mentorship, coaching, and internal promotion opportunities.
- • Generous parental leave program from day one, with top-ups for up to 26 weeks.
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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