Clearstory - VP of Product

The Role

Clearstory is looking for a seasoned Vice President of Product to lead product execution and help shape the next phase of our product strategy as we scale a proven financial workflow platform purpose-built for construction.

We have strong product-market fit, growing industry demand, high retention and expansion and billions in change orders flowing through our platform today. This role is about taking something that already works and making it exceptional.

The VP of Product sits at the intersection of Product, Engineering, and the business. You will partner closely with the CEO and executive team, bringing deep customer insight, strong product judgment, and operational rigor to turn company direction into clear product bets and consistently shipped outcomes.

You will own the end-to-end product lifecycle from discovery, prioritization, delivery, and adoption while building and leading a high-performing product organization. Your work will directly shape the only business network purpose-built to manage out-of-contract work in construction, spanning change orders, T&M tickets, allowances, pricing, and approvals, moving billions of dollars through Clearstory every month, and determining how accurately and efficiently companies get paid.

This is a senior leadership role for someone who thrives in fast-paced, scale-up environments. Someone who is comfortable with ambiguity, values strong opinions and healthy debate, and knows how to execute decisively once a direction is set. We are looking for a builder, not someone searching for their first VP role, and not someone who prefers maintaining products at rest.

If you’re excited by complex financial workflows, real customer pain, and the opportunity to define a category, this role will be both demanding and deeply rewarding.

Key Outcomes You Will Own and Drive

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.

Must Haves

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.

About You

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.

You embody Clearstory’s core values:

Be Curious

Customer Obsession

Keep It Simple

Raise the Bar

The Company You’ll Join

Clearstory is a SaaS platform modernizing how construction companies communicate, approve, and track change orders and related cost workflows. We replace paper, spreadsheets, and email with simple, trusted financial workflows that help contractors get paid accurately and on time.

We are a Series B, 100% SaaS company with strong product‑market fit, growing six‑figure deals, and a large, underserved TAM. Our customers love us, our retention is strong, and we are building for long‑term impact.

The Opportunity

As a senior leader at Clearstory, you will have an outsized impact on the product, the team, and the company’s trajectory. You will help scale a product with proven demand while shaping how product work gets done as the company grows.

This is an opportunity to lead execution at a critical moment with meaningful ownership, real influence, and the chance to help define the future of financial workflows in construction.