Clearstory – VP of Customer Success

Source-Multiplier; San Francisco (CA); Remote; USD 220,000 - 300,000; Full time

Job summary

Clearstory is seeking a VP of Customer Success to own and scale post-sale efforts, leading 12 CSMs, a CS manager, and two support agents. You’ll own GRR/NRR across enterprise, mid-market, and SMB, driving renewal planning, expansion, and a data-driven forecasting cadence.

You will build an enterprise CS motion, multi-stakeholder account plans, and governance for sustained growth, while evolving tooling and AI-assisted workflows to outperform growth in revenue under management.

Qualifications

• 10+ years in customer success, including leadership of B2B SaaS teams.
• Experience owning retention targets in a $20M–$50M ARR range.
• Proven ability to scale an enterprise CS motion across multiple segments.
• Experience managing managers and multi-site, multi-stakeholder accounts.
• Strong operating cadences, forecast discipline, onboarding and QBR programs.
• Executive presence and ability to present retention strategy to board.
• Bias for action with ownership from day one.
• Nice to have: construction or vertical SaaS experience.

Responsibilities

• Retention and expansion outcomes with GRR and NRR across enterprise, mid-market, and SMB customers, including forecasting cadence, renewal planning, and expansion strategy behind them.
• Enterprise customer strategy with executive sponsorship, multi-stakeholder account plans, and governance that grows strategic accounts year over year.
• Scale the CS organization: define coverage models, segmentation, hiring plans, and the management layer needed to scale efficiently through growth.
• Lead 12 CSMs, 1 CS manager, and 2 support agents; coach managers and build career paths.
• Maintain operating rigor with weekly and monthly cadences (portfolio reviews, call coaching, QBRs, onboarding) across segments.
• Cross-functional leadership: collaborate with Sales, Product, and Finance on renewals, escalations, and roadmap input.
• Drive efficiency and AI adoption to grow revenue under management faster than headcount.

Skills

Customer Success leadership

Enterprise renewal & expansion

Forecasting & metrics

Cross-functional collaboration

People management

Strategic account management

Job description

Location: Remote | Reports to: CRO | Department: Customer Success
About Clearstory

Clearstory is a construction change order management platform that brings clarity and control to complex projects. We replace 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 VP of Customer Success to own our entire post-sale organization and scale it through our next stage of growth. You'll lead 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.

You're not inheriting a turnaround. The team is healthy and high-performing, with documented processes, strong operating frameworks, and an established forecasting discipline. Your mandate is to take that foundation and scale it: build the management bench, deepen our enterprise motion, and design an organization that stays ahead of the company's growth rather than catching up to it.

What You'll Own

• Retention and expansion outcomes. Full accountability for GRR and NRR across enterprise, mid-market, and SMB customers, including the forecasting cadence, renewal planning, and expansion strategy behind them.

• Enterprise customer strategy. Executive-level ownership of our largest accounts, including many of the country's top general contractors. You'll build the enterprise CS motion: multi-stakeholder account plans, executive sponsorship, and the governance that grows strategic accounts year over year.

• Scaling the organization. Design the CS org for where the company is going, not where it is today. Define coverage models, segmentation, hiring plans, and the management layer needed to scale efficiently through rapid growth.

• The team. 12 CSMs, 1 CS manager, and 2 support agents. You'll coach managers, build career paths, and hire leaders who can scale with you.

• Operating rigor. Weekly and monthly cadences (portfolio reviews, call coaching, QBRs, onboarding execution) run consistently across segments, with metrics that hold up in a board deck.

• Cross-functional leadership. The face of CS with Sales (handoffs, account planning, expansion), Product (escalations, roadmap input), and Finance (renewals, forecasting).

• Efficiency and AI adoption. Evolve tooling and AI-assisted workflows so revenue under management grows faster than headcount.
  

What You'll Bring

• 10+ years in Customer Success, including 5+ years leading CS organizations at B2B SaaS companies

• Direct ownership of a retention number at a company in the $20M to $50M ARR range, ideally having scaled CS through that stage during a period of fast growth

• Significant enterprise experience: managing executive relationships, complex multi-site or multi-stakeholder accounts, and enterprise renewals and expansion

• Experience managing managers and running a multi-segment CS org

• A track record of building process that scales: operating cadences, forecast discipline, onboarding and QBR programs, and segment-specific coverage models

• Bias for execution: you move fast, make clear calls, and build structure without slowing the team down

• Executive presence. You can coach a call review in the morning and present retention strategy to the board in the afternoon

• High ownership. The number is yours from day one

Nice to have: construction 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 at a pivotal growth stage

• Inherit strength, not a turnaround: strong team, strong process, strong retention

• Real scope: retention and expansion are the engine of the business, and you'll run it

• A culture built on our values: Be Curious, Keep It Simple, Customer Obsession, Raise the Bar