Strategy & Operations, Customer Success

Ashby; San Francisco (CA); On-site; USD 140,000 - 180,000; Full time

Benefits offered by this job

Unlimited PTO

Twelve weeks paid family leave

Education budget

Health insurance premiums covered

Generous equipment budget

Job summary

Ashby is hiring a Chief Customer Success Officer (CSSO) in San Francisco to drive strategies and processes for our Customer Success team. You will enhance customer journeys, collaborate across functions, and optimize customer operations. Ideal candidates should possess SaaS literacy, strategic and analytical skills, and have experience in fast-growth environments. Join Ashby to help shape our customer-centric initiatives while enjoying benefits like unlimited PTO and top-tier health insurance.

Qualifications

• Self-starter and innately curious.
• Experience in fast-growth SaaS environments.
• Detail-oriented and committed to data accuracy.

Responsibilities

• Develop and refine CS operations processes and workflows.
• Analyze metrics and partnership with stakeholders.
• Enhance customer journey across all post-sales touch points.
• Collaborate on planning cycles and provide historical data.

Skills

SaaS literacy

Strategic mindset

Data analysis

CRM reporting

Communication skills

Tools

HubSpot

Job description

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.

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/.

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 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. 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.
• 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.

Compensation Range: $140K – $180K