Clearstory – VP of Customer Success

Source Multiplier•Walnut Creek, CA

About The Position

Clearstory is hiring a VP of Customer Success to lead and scale the entire post-sale organization through the company’s next stage of growth. The role has full accountability for gross and net revenue retention across enterprise, mid-market, and SMB customers, including forecasting, renewal planning, and expansion strategy. The VP will build the enterprise customer success motion, own executive relationships with the largest accounts, and develop the organizational structure, coverage models, segmentation, hiring plans, and management layer needed to support growth. The role leads 12 CSMs across General Contractor and Specialty Contractor segments, one CS manager, and two support agents. The VP will coach managers, establish career paths, and hire future leaders. They will maintain consistent operating cadences and metrics across segments, represent Customer Success in cross-functional work with Sales, Product, and Finance, and evolve tooling and AI-assisted workflows to grow revenue under management faster than headcount. The position reports directly to the CRO.

Requirements

10+ years of experience in Customer Success.
5+ years leading Customer Success organizations at B2B SaaS companies.
Direct ownership of a retention number at a company with $20M to $50M ARR.
Significant enterprise experience managing executive relationships, complex multi-site or multi-stakeholder accounts, and enterprise renewals and expansion.
Experience managing managers and leading a multi-segment Customer Success organization.
A track record of building scalable processes, including operating cadences, forecast discipline, onboarding and QBR programs, and segment-specific coverage models.
Strong execution orientation, with the ability to move quickly, make clear decisions, and build structure without slowing the team down.
Executive presence, including the ability to coach call reviews and present retention strategy to the board.
High ownership and accountability for retention outcomes.

Nice To Haves

Experience in construction or vertical SaaS.
Experience scaling Customer Success through the $20M to $50M ARR stage during a period of rapid growth.

Responsibilities

Own gross and net revenue retention across enterprise, mid-market, and SMB customers.
Lead the forecasting cadence, renewal planning, and expansion strategy.
Own executive-level relationships and strategy for the largest customer accounts.
Build the enterprise Customer Success motion, including multi-stakeholder account plans, executive sponsorship, and account governance.
Design the Customer Success organization, including coverage models, segmentation, hiring plans, and management structure.
Lead and coach 12 CSMs, one CS manager, and two customer support agents; build career paths and hire leaders.
Run consistent weekly and monthly operating cadences, including portfolio reviews, call coaching, QBRs, and onboarding execution.
Establish metrics and operating processes that support reliable forecasting and board-level reporting.
Lead cross-functional Customer Success work with Sales on handoffs, account planning, and expansion; with Product on escalations and roadmap input; and with Finance on renewals and forecasting.
Improve tooling and adopt AI-assisted workflows to increase revenue under management faster than headcount.