Manager, Customer Experience Operations

Tailscale

4d • Remote

About The Position

We are looking for a high-impact Customer Experience Operations Manager to join our Revenue Operations team. This is a critical, cross-functional role that 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.
If you're energized by building scalable programs, turning messy data into clear insights, and being the operational backbone of a high-growth team, this role is for you.

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.
• 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.
• 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.
• 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 Haves

• 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.

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.

Benefits

• An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
• A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
• Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
• Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
• Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own.
• Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed
• Number of Employees: 101-250 employees