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Clearstory - VP of Product

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About The Position

Clearstory is seeking a seasoned Vice President of Product to lead product execution and contribute to the evolution of its product strategy for a financial workflow platform tailored for the construction industry. The company has achieved strong product-market fit, with significant industry demand, high customer retention, and billions in change orders processed through its platform. This role focuses on enhancing an already successful product to an exceptional level. The VP of Product will operate at the nexus of Product, Engineering, and business strategy, collaborating closely with the CEO and executive team. This individual will leverage deep customer understanding, sound product judgment, and operational discipline to translate company objectives into strategic product initiatives and deliver consistent results. The role encompasses the entire product lifecycle, from discovery and prioritization to delivery and adoption, while also building and leading a high-performing product organization. The work will directly influence the development of a unique business network designed for managing out-of-contract work in construction, including change orders, T&M tickets, allowances, pricing, and approvals, processing billions of dollars monthly and impacting the accuracy and efficiency of contractor payments. This is a senior leadership position for individuals who excel in fast-paced, scaling environments, are comfortable with ambiguity, value diverse perspectives and constructive debate, and can execute decisively. The ideal candidate is a builder, not someone seeking their first VP role or preferring to maintain existing products. The role offers a demanding yet rewarding experience for those passionate about complex financial workflows, genuine customer challenges, and category definition.

Requirements

  • 10+ years of total professional experience.
  • 3–5+ years leading a Product organization.
  • Experience building fintech, financial workflow, billing, payments, accounting, or revenue‑critical B2B SaaS products.
  • Proven experience scaling products in fast‑growing SaaS environments.
  • Strong cross‑functional partnership skills with Engineering, Sales, and Customer Success.
  • Ability to operate effectively in ambiguity and make high‑quality tradeoffs.
  • Excellent written and verbal communication skills.
  • You are a senior product leader who enjoys close partnership with a CEO and executive team.
  • Brings strong opinions backed by customer insight and data, and collaborates well through disagreement.
  • Is execution‑oriented and accountable for outcomes, not just ideas.
  • Cares deeply about simplicity, trust, and quality in revenue‑critical systems.
  • Thrives in high‑growth environments with constant change.
  • Embody Clearstory’s core values: Be Curious, Customer Obsession, Keep It Simple, Raise the Bar.

Responsibilities

  • Help Shape and Execute a Clear Product Direction
  • Partner with the CEO and executive team to refine, document, and operationalize Clearstory’s product strategy.
  • Translate customer, market, and business insights into clear product narratives, product briefs, and decision frameworks that drive alignment and tradeoffs.
  • Ensure tight alignment across Product, Engineering, Sales, Marketing, and Customer Success on product vision, priorities, and sequencing—from discovery through release.
  • Execute with Speed, Quality, and Discipline
  • Own a rigorous, repeatable product development process that leverages AI-assisted workflows for PRDs, product briefs, discovery synthesis, and roadmap planning.
  • Drive roadmap development, prioritization, and delivery with clarity, predictability, and measurable outcomes.
  • Champion rapid prototyping, validation, and iteration using modern tooling to reduce cycle time from idea to customer value.
  • Partner closely with Engineering leadership to continuously improve discovery quality, execution velocity, and delivery confidence.
  • Build and Scale a High-Performing Product Organization
  • Hire, mentor, and develop strong product leaders and ICs who combine strategic thinking with operational excellence.
  • Establish and own clear product operating rhythms across discovery, planning, execution, launch readiness, and retrospectives.
  • Raise the bar for product rigor, clarity, and simplicity—ensuring decisions, tradeoffs, and priorities are well-documented and well-understood as the team scales.
  • Build a product team that is deeply AI-forward in how it works, not just what it builds.
  • Drive Measurable Business Impact
  • Ensure product execution directly supports retention, expansion, and competitive differentiation.
  • Own the product side of software releases, ensuring tight coordination with Marketing, Sales, and Customer Success on positioning, enablement, and rollout.
  • Equip go-to-market teams with clear product context, narratives, and artifacts to support strategic and competitive deals.
  • Use data, customer feedback, and strong judgment to continuously refine priorities, investments, and bets.

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