About Tailscale Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We’re building a future for the Internet that’s easy, sensible, and safe, like it used to be. Job Overview We are looking for a high‑impact Customer Experience Operations Manager to join our Revenue Operations team. This critical, cross‑functional role sits at the intersection of strategy, data, and execution, supporting our global post‑sales organization—including Customer Success, Customer Success Engineering, and Support Engineering—to operate at scale and deliver exceptional customer outcomes. You’ll partner closely with CS leadership, Revenue Operations, Finance, and Product to design and run the operational systems, processes, and insights that drive retention, expansion, and customer health across our portfolio. You’ll shape how our post‑sales teams operate, influence strategic decisions, and directly impact our ability to deliver world‑class customer experiences. Key Responsibilities Run and Scale CS Operations Own the operational rhythm of the Customer Experience organization: reporting cadences, QBRs, renewal forecasting, health scoring, capacity modeling, and tooling. Design and implement the customer journey alongside Product, Marketing, and other cross‑functional partners to ensure proper coverage of customer accounts. Define and implement customer health scoring models that incorporate product usage, support signals, and engagement data to surface risk and opportunity proactively. Implement automated workflows to process renewals and customer programs at scale. Maintain data integrity across post‑sales systems (Salesforce, CS Platform, BI tools) to ensure CS, CSE, and Support teams have reliable, actionable data. Drive Strategy, Planning, and Segmentation Partner with post‑sales leadership to define customer segmentation, coverage models, and engagement strategies across CS, CSE, and Support Engineering. Support annual and quarterly planning, including capacity modeling across all post‑sales functions. Align post‑sales motions with company‑level goals including NRR, GRR, product adoption, and support SLAs. Drive Insights and Program Execution Translate data signals into proactive recommendations, surfacing trends in customer health, churn risk, product adoption, and team performance for CS leadership. Build and maintain dashboards and reporting across customer health and risk, support performance (SLAs, backlog, resolution time), product adoption and engagement, and retention and expansion metrics. Receive feedback from CS, CSE, and Support teams to define and prioritize strategic projects and process improvements. Own Cross‑Functional Programs Work cross‑functionally with Revenue Operations, Finance, Product, and Marketing to support operational programs aligned to broader organizational strategy. Improve handoffs between teams (Sales to CS to Support to Engineering) to ensure a seamless, consistent customer experience. Identify tooling and process gaps and own the roadmap to close them, leveraging automation and AI to drive efficiency. Enable the Post‑Sales Team Develop and operationalize lifecycle programs and playbooks across CS, CSE, and Support covering onboarding, success plans, risk mitigation, escalations, expansion, and renewals. Act as the primary point of contact for post‑sales tooling, including CS platform administration, Salesforce integrations, and BI reporting. What We Are Looking For Experience 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. Proven experience designing and executing programs that scale, from ideation through implementation and measurement. Experience supporting multi‑functional post‑sales teams (Customer Success, Customer Success Engineering, Support Engineering, Renewals, or Professional Services) is strongly preferred. Track record of working cross‑functionally and building trust with stakeholders across CS, Sales, Finance, and Product. Experience with renewal operations and post‑sales GTM motions including expansion and professional services. Technical Skills 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 support tooling such as Jira Service Management. Familiarity with SQL or BigQuery is a strong plus; data fluency is essential. Familiarity with AI‑driven tooling or workflow automation platforms to improve post‑sales productivity and scale customer programs. Mindset and Ways of Working Systems thinker who can connect workflows across CS, CSE, Support, and Revenue teams. Strong analytical skills with the ability to build and interpret complex data, identify the key insights, and communicate them clearly to any audience. Customer‑first orientation with a genuine passion for improving the post‑sales experience through better process and tooling. 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. Comfortable operating in ambiguity and building from scratch as the organization grows. Excellent written and verbal communication skills with the ability to manage multiple workstreams simultaneously. Nice to Have Experience in a high‑growth startup environment. Familiarity with product usage analytics tools such as Amplitude or Pendo. Experience with PLG or hybrid sales motions. Experience building or maturing a CS Operations function from scratch. Background working closely with Engineering or Support organizations. What Success Looks Like A unified, seamless experience across CS, Customer Success Engineering, and Support Engineering, with clear ownership and consistent handoffs at every stage. Customer segmentation and coverage models that are well‑defined, actively maintained, and aligned to company growth goals. Scalable systems and processes that measurably improve team efficiency and reduce manual work across post‑sales functions. Leadership has clear, real‑time visibility into customer health, risk, support performance, and expansion opportunity. Measurable improvements in Net Revenue Retention (NRR) and Gross Revenue Retention (GRR). Improved customer satisfaction as reflected in CSAT and NPS scores. Faster time‑to‑resolution and stronger support SLA performance across Support Engineering. Strong cross‑functional alignment between post‑sales, Product, and Sales that accelerates both retention and expansion. What We Offer An inclusive, flexible environment where you can be your authentic self. A competitive total compensation package including base salary, equity, and variable commission (for quota‑based roles). Comprehensive group benefits with no waiting period for health, vision, dental, and more. Remote‑first company: most teams work fully remotely; occasional in‑office collaboration noted in the job description. Support for personal and professional development with annual funding and internal growth opportunities. Paid time off and a healthy work‑life integration program. Build‑your‑own home office setup with equipment, internet reimbursement, and customization allowance. Generous parental leave program from day one. Location Requirement Applicants must reside in Canada to be considered for this position. We are not currently providing relocation or immigration support for this role. Equal Employment Opportunity As set forth in Tailscale’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law. #J-18808-Ljbffr