Head of Customer Success & Retention (Remote)

Clearstory; San Francisco (CA); Hybrid; USD 180,000 - 260,000; Full time

Benefits offered by this job

Subsidized healthcare

Vision & dental

Early equity

Remote work schedule

Executive interaction

Job summary

Clearstory is seeking a Senior Director of Customer Success to own our post-sale organization, including 12 CSMs, a growing management layer, and customer support. You will oversee GRR/NRR across segments, manage executive relationships with top customers, and report to the CRO.

You’ll inherit a high-performing team with established processes and a disciplined forecasting cadence. This role offers ownership, scale, and a path to broader operational impact as the company grows.

Qualifications

• 8+ years in Customer Success, including 4+ years leading CS teams at B2B SaaS companies.
• Experience managing managers and running a multi-segment CS org.
• Direct ownership of a retention number at a company between $10M-$50M ARR.
• A track record of building repeatable process: operating cadences, forecast discipline, onboarding and QBR programs.
• Executive presence — you can coach a call review in the morning and present retention strategy to the board in the afternoon.
• A high-ownership mindset: the number is yours from day one.

Responsibilities

• Own the entire post-sale organization: 12 CSMs across two segments, growing management layer and support.
• Coach managers, develop career paths, and complete open hiring on the management layer.
• Own enterprise relationships with our largest customers.
• Enforce weekly and monthly operating cadences across segments: portfolio reviews, call coaching, QBRs, onboarding execution.
• Serve as the face of CS in cross-functional leadership with Sales, Product, and Finance on renewals and forecasting.
• Drive efficiency and AI-enabled workflows to grow revenue under management faster than headcount.

Skills

Customer Success Leadership

B2B SaaS

People Management

Executive Presence

Forecasting

Job description

Clearstory is seeking a Senior Director of Customer Success to own our post-sale organization, including 12 CSMs, a growing management layer, and customer support. You will oversee GRR/NRR across segments, manage executive relationships with top customers, and report to the CRO.

You’ll inherit a high-performing team with established processes and a disciplined forecasting cadence. This role offers ownership, scale, and a path to broader operational impact as the company grows.