# Strategy & Operations, Customer Success Remote from[USA](https://jobicy.com/job-region/usa.md), [Canada](https://jobicy.com/job-region/canada.md)Salary, yearly, USD 140,000 - 180,000Department [Product & Operations](https://jobicy.com/categories/management.md) Employment type Full Time, Job posted20 Jul 2026Apply before20 Aug 2026Views / Applies 109 / 5 [About company](https://jobicy.com/company/ashby.md) * Share About [Ashby](https://jobicy.com/company/ashby.md) Ashby helps scaling companies achieve their ambitious growth targets by running a fast and efficient hiring process. [Computer Software](https://jobicy.com/company-category/software.md) * 2018 Actively Hiring Verified job posting This job post has been [manually reviewed](https://jobicy.com/tools/help-center/employee/how-does-jobicy-verify-the-legitimacy-of-remote-job-listings.md) for authenticity and compliance. ### AI Summary This Strategy & Operations role within Customer Success at Ashby focuses on driving strategy, processes, and data-driven insights to optimize customer health, retention, and revenue growth. The position involves operationalizing CS strategy, analyzing business metrics like NRR and churn, and enhancing the end-to-end customer journey. It requires close collaboration with CS leadership, Finance, and cross-functional teams to support planning and process improvements. The ideal candidate is a self-starter with SaaS and financial literacy, comfortable with both strategic and tactical execution in a fast-growth environment. This role offers a salary range of $140,000 to $180,000 per year. ### Role DNA Job Complexity Easy Hard Pace & Pressure Relaxed Fast-paced Autonomy Level Guided Full Ownership Communication Load Independent Highly Collaborative AI Insight The role demands strategic thinking, data analysis, cross-functional collaboration, and change management in a fast-paced SaaS environment, requiring a blend of high-level strategy and hands-on execution, which is challenging. ### Salary Analysis Median Highly Competitive USD160,000US Market USD100k – 200k 0 USD220k AI Insight The offered salary of $140,000 - $180,000 is competitive for a Senior Strategy & Operations role in Customer Success, aligning with market rates for experienced professionals in high-growth SaaS companies. ### Core Skills Required [Customer Success Operations](https://jobicy.com/jobs?search_keywords=Customer+Success+Operations.md) [Revenue Operations](https://jobicy.com/jobs?search_keywords=Revenue+Operations.md) [Data Analysis](https://jobicy.com/jobs?search_keywords=Data+Analysis.md) [Process Improvement](https://jobicy.com/jobs?search_keywords=Process+Improvement.md) [CRM Management](https://jobicy.com/jobs?search_keywords=CRM+Management.md) [Cross-functional Collaboration](https://jobicy.com/jobs?search_keywords=Crossfunctional+Collaboration.md) [Strategic Planning](https://jobicy.com/jobs?search_keywords=Strategic+Planning.md) [SaaS](https://jobicy.com/jobs?search_keywords=SaaS.md) [Customer Health Scoring](https://jobicy.com/jobs?search_keywords=Customer+Health+Scoring.md) [Change Management](https://jobicy.com/jobs?search_keywords=Change+Management.md) ### Cover Letter Sample Dear Hiring Manager, I am excited to apply for the Strategy & Operations, Customer Success role at Ashby. With over five years of experience in revenue operations and customer success strategy at high-growth SaaS companies, I have a proven track record of driving process improvements and data-informed decisions that enhance customer retention and revenue growth. In my previous role, I led the development of customer health scoring models and optimized onboarding workflows, resulting in a 15% increase in net revenue retention. I am skilled in CRM tools like HubSpot and have deep expertise in analyzing metrics such as NRR, GRR, and churn to guide strategic initiatives. I am particularly drawn to Ashby's commitment to customer care and would welcome the opportunity to contribute to your team's evolution. Thank you for considering my application. Copy ### Sample Interview Questions How would you approach optimizing the customer journey from onboarding to renewal?I would start by mapping the current journey to identify friction points, then collaborate with CS, Product, and Support to implement improvements. Key metrics like time-to-value and NPS would be tracked to measure impact, and I would iterate based on feedback and data.Describe a time you used data to influence a strategic decision in Customer Success.At my previous company, I analyzed churn data and found that customers who didn't receive a product training within the first 30 days had a 40% higher churn rate. I presented this insight to leadership, leading to a mandatory onboarding training program that reduced churn by 20%.How do you handle competing priorities from multiple stakeholders?I prioritize by aligning with business goals and assessing impact versus effort. I communicate openly with stakeholders about trade-offs and set clear expectations. Using tools like a RACI matrix helps ensure everyone is aligned and informed.What experience do you have with CRM reporting and tools like HubSpot?I have extensive experience with HubSpot, including building custom dashboards, automating workflows, and integrating with other tools. At my last role, I created a health scoring system in HubSpot that improved early warning identification for at-risk accounts.Can you give an example of a change management initiative you led?I led the rollout of a new customer segmentation framework. I created training materials, held workshops, and established feedback loops. By involving key stakeholders early and addressing concerns, adoption reached 90% within two months, leading to more targeted services. Role Overview In this CSSO 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 Senior Manager of Revenue 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 / Career Deep Dive – 60 minutes * Challenge Interview – 45 Minutes * Final Round / Virtual Onsite – 2 hours ## About Ashby We’re building the next generation of enterprise software, and we’re starting with a suite of products that help talent leaders, recruiters, and hiring managers run their hiring process significantly better. Learn more on our website:[https://www.ashbyhq.com/](https://www.ashbyhq.com/) We are well funded and backed by great investors, including Y Combinator, Elad Gil and Lachy Groom. We have thousands of amazing customers including Snowflake, OpenAI, Shopify, Ramp, Notion, and Zapier (and many others who we cannot name!). Our growth and retention metrics are best-in-class among our peers: we have tens of millions in ARR, growing >100% year over year, very low churn, and many years of runway. We’ll share more details once we meet. In short, it’s the perfect time to join! 🚀 ## 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/149439-strategy-operations-customer-success.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. 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