[All remote jobs](https://jobicy.com/jobs.md)[![Ashby logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/08/63864ee6-221.png)](https://jobicy.com/company/ashby.md)[Ashby](https://jobicy.com/company/ashby.md) # Strategy & Operations, Customer Success AI Summary Ashby is hiring a Strategy & Operations professional to scale Customer Success processes, systems, reporting, and strategic planning. The role analyzes retention, churn, adoption, health, and customer-sentiment metrics to produce actionable recommendations for CS leadership. Responsibilities span customer segmentation, lifecycle design, capacity modeling, KPI deployment, CRM and health-scoring improvements, and change management. This is a cross-functional, hands-on role partnering closely with Customer Success, Finance, Sales, Product, RevOps, and Enablement. Success requires strong SaaS and financial literacy, analytical rigor, autonomous execution, and clear stakeholder communication.[Apply for this job](#job-application)[View company](https://jobicy.com/company/ashby.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md), [Canada](https://jobicy.com/job-region/canada.md)SalaryUSD 175k–221,875 / yrDepartment[Product & Operations](https://jobicy.com/categories/management.md)EmploymentFull TimeExperienceSeniorPublished6 Nov 2026Apply before6 Dec 2026Listing views86Application actions5Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. Opportunity details ## About this role. ### Role Overview In this Strategy and Operations, Customer Success role, you will drive the strategy, processes, and data-driven insights that empower our Customer Success Team to deliver exceptional outcomes for our customers. Reporting to the Manager of Strategy and Operations, and partnering closely with Customer Success leadership, you will define strategies and execute improvements that optimize customer health, retention, and revenue growth. Our Customer Success team is consistently praised by our customers for their deep expertise, responsiveness, and dedication—a testament to how much we Care Deeply About Customers, one of our core Operating Principles. As we continue to scale, it’s critical that we preserve and enhance this high standard of customer care while ensuring our processes, tools, and insights evolve to support sustainable growth. You will play a crucial role in our operations, including process improvements, planning, and reporting. This is both a strategic and tactical role in which you’ll design frameworks and programs, uncover actionable insights, and create data-informed recommendations across our Customer Success functions. ### What you’ll do at Ashby: * Operationalize CS Strategy: Develop and refine processes, tools, and workflows to scale Customer Success operations. This includes customer segmentation, onboarding workflows, lifecycle mapping, and playbook development. * Analyze Business Dynamics: Partner with internal stakeholders on reporting & analysis of metrics such as NRR, GRR, churn, product adoption, health score, and customer sentiment. Use these insights to provide early warnings and refine CS strategies. * Optimizate the Customer Journey: Enhance the end-to-end customer journey, ensuring smooth transitions across all post-sales touch points from onboarding through support and renewal. * Support Strategic Planning: Collaborate with Finance and CS leadership on planning cycles, including headcount planning, capacity modeling, and quota setting. Provide relevant historical data for informed decision making. * Drive Process Improvements: Identify inefficiencies and implement improvements to CS workflows, customer onboarding, account transitions, and renewal processes. Implement & deploy KPIs to measure performance against strategic initiatives. * Optimize CS Systems: Define the business requirements to improve Customer Success efficiency, efficacy, and scalability. Partner with RevOps teammates to implement changes to tools (CRM, health scoring platforms, etc) * Collaborate Cross-functionally: Ensure alignment with Sales, Product, and other teams to align resources with customer needs and forecasted growth. * Support Change Management: Lead the roll-out and adoption of new processes or workflows to the CS team. Partner with Enablement on larger scale change programs. ### You could be a great fit if you: * Are a self-starter, innately curious in your approach * Bring both SaaS & financial literacy, offering an informed perspective on CS benchmarks (e.g.ideal book sizes) * Have a strategic mindset, with the ability to distill data into actionable recommendations * Are detail-oriented and committed to data accuracy and process quality * Have experience in fast-growth SaaS environments, ideally in a Customer Success or Revenue Operations role * Are skilled in CRM reporting, with preference for HubSpot experience * Work autonomously, managing multiple tasks and deadlines effectively * Are an excellent communicator, both verbally and in writing ### This role may not be a fit if: * You’re unwilling to manage both high-level strategy and hands-on execution * You’re uncomfortable with ambiguity and prefer structured, predefined assignments * You prefer focused work on a single project at a time * You prefer working within a single team rather than across multiple teams ### Interview Process Our interview process is thorough — we aim to ensure each person joining the team is the right fit for Ashby and will provide ample information to assess if Ashby is the right fit for you. The process for this role is as follows: * Recruiter Screen with Talent Acquisition Team – 30 minutes * Hiring Manager Interview – 45 minutes * Challenge Interview – 45 minutes * Virtual Onsite – 90 min ### Benefits * 10-year exercise window for stock options. You shouldn’t feel pressure to purchase stock options if you leave Ashby —do it when you feel financially comfortable. * Unlimited PTO with four weeks recommended per year. Expect “Vacation?” in our one-on-one agenda until you start taking it 😅. * Twelve weeks of fully paid family leave in the US. We plan to expand this to employees in other countries as situations arise. * Generous equipment, software, and office furniture budget. Get what you need to be happy and productive! * $100/month education budget with more expensive items (like conferences) covered with manager approval. * If you’re in the US, top-notch health insurance for you and your dependents, with all premiums covered by us. Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities. Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position. Show more [Apply now >](https://jobicy.com/jobs/159400-strategy-operations-customer-success-2.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 4/5EasyHard ### Pace & Pressure 4/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThe position combines strategic operating design with detailed analytical and implementation work across several teams. It requires comfort with ambiguity, customer-success economics, system requirements, and competing priorities in a fast-growth SaaS environment. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Highly competitive$198,437.50US market range (per year)$165k–$230k0$253.00k AI insightThe employer discloses a base salary range of $175,000–$221,875 USD per year, with a midpoint of $198,437.50. This is a credible annual range for a senior Customer Success Strategy & Operations role in the US/Canada remote SaaS market. Estimated market pay is $165,000–$230,000 USD per year; actual offers may vary by location, experience, and scope. ## Core skills Skills and capabilities most closely associated with this opportunity. [Customer Success Operations](https://jobicy.com/jobs?search_keywords=Customer%20Success%20Operations.md)[SaaS Strategy](https://jobicy.com/jobs?search_keywords=SaaS%20Strategy.md)[Business Analytics](https://jobicy.com/jobs?search_keywords=Business%20Analytics.md)[Customer Retention](https://jobicy.com/jobs?search_keywords=Customer%20Retention.md)[Churn Analysis](https://jobicy.com/jobs?search_keywords=Churn%20Analysis.md)[Net Revenue Retention](https://jobicy.com/jobs?search_keywords=Net%20Revenue%20Retention.md)[Customer Segmentation](https://jobicy.com/jobs?search_keywords=Customer%20Segmentation.md)[Lifecycle Management](https://jobicy.com/jobs?search_keywords=Lifecycle%20Management.md)[CRM Reporting](https://jobicy.com/jobs?search_keywords=CRM%20Reporting.md)[HubSpot](https://jobicy.com/jobs?search_keywords=HubSpot.md)[Capacity Planning](https://jobicy.com/jobs?search_keywords=Capacity%20Planning.md)[KPI Development](https://jobicy.com/jobs?search_keywords=KPI%20Development.md)[Process Improvement](https://jobicy.com/jobs?search_keywords=Process%20Improvement.md)[Change Management](https://jobicy.com/jobs?search_keywords=Change%20Management.md)[Cross-functional Collaboration](https://jobicy.com/jobs?search_keywords=Cross-functional%20Collaboration.md) Sample interview questionsHow would you use NRR, GRR, churn, adoption, and health-score data to prioritize Customer Success initiatives?I would first validate metric definitions and segment the data by customer cohort, size, lifecycle stage, product usage, and CSM ownership. I would identify leading indicators correlated with churn or expansion, quantify the affected revenue, and prioritize interventions by expected impact, urgency, and implementation effort. I would then establish KPIs and review the results with CS leadership on a regular cadence. Describe how you would design a scalable customer segmentation model. I would combine commercial attributes such as ARR, growth potential, and renewal risk with operational factors such as complexity, product maturity, support needs, and engagement signals. Each segment would have a clearly defined service model, engagement cadence, ownership model, and success playbook. I would pilot the model, measure outcomes such as retention and CSM capacity, and refine it before wider rollout. How would you approach a capacity-planning exercise for a growing Customer Success organization? I would model current books of business, account complexity, customer-contact requirements, renewal timing, and expected growth by segment. I would translate those assumptions into CSM capacity ranges and compare the demand forecast with current staffing, ramp time, and hiring plans. The output would include headcount scenarios, risks, and recommended trigger points for hiring. Tell us how you would lead adoption of a new CS workflow or CRM process. I would begin by documenting the business problem, desired behavior, process owners, and success measures. I would involve representative users in design and testing, provide concise enablement materials, and launch with clear expectations and feedback channels. After rollout, I would monitor adoption and data quality, resolve friction points, and communicate measured improvements to the team. What makes a recommendation to Customer Success leadership persuasive? A persuasive recommendation connects a verified business problem to customer and revenue impact, presents the relevant data clearly, and offers a practical path to action. I would state assumptions, trade-offs, resourcing needs, and measurable success criteria rather than presenting analysis alone. Tailoring the message to the audience and inviting stakeholder input also helps build alignment and accountability. Next step ## Apply now. Follow the employer’s application method and review Jobicy’s safety guidance before sharing personal information. Keep exploring ## Related remote jobs. * ![Nebius logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2026/06/d90c0566-221.webp) Nebius Nov 6 New ### [Transportation Logistics Specialist](https://jobicy.com/jobs/159438-transportation-logistics-specialist.md) About Nebius: Nebius is leading a new era in cloud infrastructure for the global AI economy. 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