Manager, Customer Experience Operations

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. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Job Description

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.

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.

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.

CAN Pay Range (OTE)

$268,000—$268,000 CAD

Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

What We Offer

• 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.

 

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