Customer Success Strategy & Operations

About Ashby

• We’re building the next generation of enterprise software, starting with products that help talent leaders, recruiters, and managers unlock hiring excellence

• Series C raised earlier this year, and growing ARR >100% YoY

• Have thousands of amazing customers including OpenAI, Ramp, Deliveroo, Notion and Reddit

• Multiple products to win both land-and-expand and material new business deals

• Rapidly moving up-market with no signs of slowing down

• Implemented AI throughout the platform

• Known for our pace of innovation and advanced analytics

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 Head 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.

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 systems, uncover actionable insights, and create data-informed recommendations across all Customer Success functions, including our CSM teams, Professional Services, Contract Management, and Support.

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.

• Optimize 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)

• Cross-functional Collaboration: 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