Senior Director of Customer Success

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.

• 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 Q  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.

• 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  a company, we value fairness, collaboration, communication, and leadership and build our teams around these values.