Senior Director of Customer Success

Clearstory

2d•Remote

About The Position

Clearstory is a construction change order management platform that brings clarity and control to complex projects. We replace the traditional methods of tracking change orders — email, Excel, and paper — with intelligent automation and real-time collaboration between GCs, specialty contractors, and owners. Teams on Clearstory share over $2B in CORs monthly, and more than 50% of ENR's Top 50 GCs trust the platform. We're a ~100-person, Series B company headquartered in San Francisco with a distributed team across the US. We're hiring a Senior Director of Customer Success to own our entire post-sale organization: a team of 12 CSMs across two segments (General Contractors and Specialty Contractors), a growing management layer, and customer support. You'll be accountable for gross and net revenue retention across the customer base and report directly to the CRO. This is a rare setup: you're inheriting a healthy, high-performing team with strong operating frameworks, documented processes, and an established forecasting discipline — built by a leader who is moving into a company-wide operations role. Your mandate isn't to fix something broken. It's to take full ownership, develop the management bench, and scale the organization ahead of the company's growth.

Requirements

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

Nice To Haves

construction industry or vertical SaaS experience. Our CSMs bring deep domain expertise — we need you to bring world-class CS leadership.

Responsibilities

Retention outcomes. Full accountability for GRR and NRR across enterprise, mid-market, and SMB customers — including the forecasting cadence and retention planning that drive them.
The team. 12 CSMs, 1 CS manager, and 2 support agents. You'll coach managers, develop career paths, and complete open hiring on the management layer.
Enterprise relationships. Direct ownership of executive relationships with our largest customers.
Operating rigor. Weekly and monthly operating cadences — portfolio reviews, call coaching, QBRs, onboarding execution — enforced consistently across segments.
Cross-functional leadership. The face of CS with Sales (handoffs, account planning), Product (escalations, feature input), and Finance (renewals, forecasting).
Efficiency and AI adoption. Evolving coverage models, tooling, and AI-assisted workflows so revenue under management grows faster than headcount.