About ClearstoryClearstory 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 RoleWe'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 OwnRetention 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.Requirements8+ years in Customer Success, including 4+ years leading CS teams at B2B SaaS companiesExperience managing managers and running a multi-segment CS orgDirect ownership of a retention number at a company between $10M–$50M ARRA track record of building repeatable process: operating cadences, forecast discipline, onboarding and QBR programsExecutive presence — you can coach a call review in the morning and present retention strategy to the board in the afternoonA high-ownership mindset: the number is yours from day oneNice 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 RoleOwn a complete functionInherit strength, not a turnaround — strong team, strong process, strong retentionReal scope: retention is the engine of the business at this stage, and you'll run itA company culture built on our values: Be Curious, Keep It Simple, Customer Obsession, Raise the BarBenefits 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 recruiting@clearstory.build. As a company, we value fairness, collaboration, communication, and leadership and build our teams around these values.
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.
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 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
Benefits
- 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 recruiting@clearstory.build. As a company, we value fairness, collaboration, communication, and leadership and build our teams around these values.
At Clearstory we make the construction industry more efficient by using technology to better communicate project costs between companies.The construction industry is being transformed fast by technology but the way companies communicate costs hasn’t evolved in decades and still heavily relies on carbon copy paper, spreadsheets and email to track billions of dollars. These arcane manual processes can take days or weeks and include hours of manual office tasks such as scanning, manually transcribing, and tedious data-entry into spreadsheets.In an industry with constant change, large amounts of capital and thin margins, this results in a massive loss of valuable time and money for hard working contractors.Clearstory creates tools to help contractors dramatically increase their organization and efficiency with a brand new category, called “change order communication,” by intelligently digitizing this age-old process. This leads to an increase in profits, more successful contractor to customer relationships, more transparency into a project’s true cost, and less wasted paper!
At Clearstory we make the construction industry more efficient by using technology to better communicate project costs between companies.
The construction industry is being transformed fast by technology but the way companies communicate costs hasn’t evolved in decades and still heavily relies on carbon copy paper, spreadsheets and email to track billions of dollars.
These arcane manual processes can take days or weeks and include hours of manual office tasks such as scanning, manually transcribing, and tedious data-entry into spreadsheets.
In an industry with constant change, large amounts of capital and thin margins, this results in a massive loss of valuable time and money for hard working contractors.
Clearstory creates tools to help contractors dramatically increase their organization and efficiency with a brand new category, called “change order communication,” by intelligently digitizing this age-old process. This leads to an increase in profits, more successful contractor to customer relationships, more transparency into a project’s true cost, and less wasted paper!
