Senior Director of Customer Success

About Clearstory 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. The Role 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. What You'll Own 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. 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 have: construction industry or vertical SaaS experience. Our CSMs bring deep domain expertise — we need you to bring world-class CS leadership. Why This Role Own a complete function Inherit strength, not a turnaround — strong team, strong process, strong retention Real scope: retention is the engine of the business at this stage, and you'll run it A company culture built on our values: Be Curious, Keep It Simple, Customer Obsession, Raise the Bar Ability to work with a new product category that has already found product market fit Remote work schedule Executive interaction regularly Competitive market-rate salary for a Series B company Subsidized healthcare, vision, and dental Early equity! We are an equal opportunity employer and are committed to providing a positive interview experience for every candidate. If accommodations due to a disability or medical condition are needed, connect with us via email at [email protected]. As a company, we value fairness, collaboration, communication, and leadership and build our teams around these values.