Director of Product

FairSquare•San Diego, CA

10d•$139,000 - $190,000•Hybrid

About The Position

Responsible for leading the evolution of FairSquare’s SMB financing ecosystem across multiple brands and platforms. Define and drive strategy for one or more major growth domains that accelerate business performance, strengthen borrower trust, and create scalable value. You keep a pulse on where AI is headed, tracking new models, emerging tools, and fresh research, and translate that into a point of view on what it means for SMB financing products. Partner closely with the VP of Product Development to shape how the Company makes product decisions: embedding impact-driven frameworks, clarifying priorities, and elevating how Product influences company strategy. This role requires system-level thinking — understanding the logical and organizational interconnections that drive outcomes — paired with clarity, structured judgment, and calm leadership. Collaborate with Business Unit Leaders, PMO, Engineering, Data, Sales, Operations, Marketing, CX, and Risk — not just to deliver initiatives, but to institutionalize how the company defines, prioritizes, and measures product impact across the full customer lifecycle.

Requirements

A genuine drive to help small business owners succeed — seeing product outcomes not just as metrics, but as ways to empower real entrepreneurs and communities.
8–10+ years in Product Management, with a proven record leading complex, cross-functional initiatives in fintech, SaaS, or SMB lending.
Hands-on fluency with AI tools: you use them daily to research, analyze, prototype, and accelerate your own work, and can demonstrate how doing so has improved the quality, speed, or depth of your product decisions.
Technically conversant: able to partner with engineers to understand technical and AI/LLM tradeoffs and write requirements that account for them.
A player-coach mindset: comfortable owning strategy through execution personally, doing the work of shaping insight, spec, and prototype.
Strong track record of turning strategic goals into measurable outcomes that improve customer and business performance.
Deep experience defining and applying frameworks to structure decisions and communicate product rationale.
Proven ability to drive lifecycle impact from acquisition and activation to retention and revenue.
Expertise in balancing borrower needs, business value, and operational feasibility in a multi-stakeholder environment.
Exceptional leadership and communication skills — able to influence executive levels through structured reasoning and clarity.
Comfortable operating in dynamic, data-informed environments; disciplined yet pragmatic.

Nice To Haves

Experience shipping AI-powered product features is a plus.
Strongly preferred: experience operating within the SMB financing, embedded finance, or lending marketplace ecosystem.
Familiarity with technologies that enable the full product development lifecycle — including customer data systems, workflow automation, partner integrations, analytics, and digital experience platforms — is highly valued.

Responsibilities

Lead the development of strategy and roadmap for your assigned growth domain(s), aligned with FairSquare’s product vision and long-term business objectives.
Define lifecycle metrics and initiatives that drive sustainable growth and customer value.
Push the edge of what’s possible with AI for our borrowers, staying ahead of new tools and models as the landscape evolves.
Partner with PMO and Technology to operationalize evaluation frameworks that ensure prioritization reflects measurable business impact and scalability.
Bring a point of view on where AI creates real advantage for borrowers, and where it introduces risk instead.
Anticipate dependencies across initiatives and align stakeholders to balance near-term performance with long-term platform evolution.
Translate business goals into structured, data-informed product hypotheses, plans, and measurable success metrics.
Build alignment across executive, technical, and commercial stakeholders by articulating tradeoffs, rationale, and expected outcomes with clarity.
Co-create with functional leaders to establish product plans and ensure new capabilities are fully adopted and integrated into borrower and partner journeys.
Drive a culture of shared accountability — ensuring each initiative is grounded in customer impact and business results.
Foster transparency through structured planning, documentation, and communication.
Serve as a trusted thought partner to Business Unit and Technology leaders, extending Product’s influence beyond feature delivery.
Establish pre-launch success criteria and ensure every initiative begins with a clear definition of impact, aside from defining roadmaps at the epic level.
Lead quarterly and annual reviews to evaluate portfolio performance, ROI, adoption, and lifecycle impact, including the performance of AI-driven or automated capabilities against lending-specific KPIs (e.g., approval rate, time-to-fund, loss rate, servicing cost).
Collaborate with Data and Finance to evolve how FairSquare measures product contribution to growth, retention, and efficiency.
Encourage a culture of learning through reflection, iteration, and data-driven decision-making.
Model calm, rational decision-making under ambiguity — providing clarity when direction is uncertain.
Promote collaboration, informed judgment, and organizational agility by fostering open communication, constructive dialogue, and partnership built on trust.
Codify and scale the way Product leads across FairSquare — embedding structure, clarity, and continuous learning in every initiative.
Other duties as assigned.