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About the Role

Responsible for leading the evolution of FairSquare’s SMB financing ecosystem across multiple brands and platforms. Define and drive strategy for major growth domains that accelerate business performance, strengthen borrower trust, and create scalable value. This role requires system-level thinking, clarity, structured judgment, and calm leadership.

Responsibilities

Lead the development of strategy and roadmap for 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 borrowers, staying ahead of new tools and models.
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.
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.
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.
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.

Requirements

A genuine drive to help small business owners succeed.
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: use them daily to research, analyze, prototype, and accelerate work, and demonstrate how doing so has improved 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.
Experience operating within the SMB financing, embedded finance, or lending marketplace ecosystem is strongly preferred.
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.
Working in a temperature-controlled office environment.
Sitting at a desk for long periods of time while viewing multiple computer screen monitors.
Potential lifting of boxes around 5-10lbs.

Skills

AI tools
Product Management
Fintech
SaaS
SMB lending
Technical communication
Strategic planning
Data analysis
Leadership
Communication
SMB financing
Embedded finance
Lending marketplace
Customer data systems
Workflow automation
Partner integrations
Analytics
Digital experience platforms

Location

San Diego, CA (La Jolla/UTC)
Irvine, CA
Atlanta, GA
Orlando, FL
Remote (US)

Work Type

Hybrid
Full-time

Experience Level

8-10+ years in Product Management

Salary/Compensations

$139K-190K plus Bonus

Benefits

Bonus
401(k) match
Health and welfare benefits
Amazing culture
Growth opportunity

About the Company

FairSquare is building the future of SMB finance. We combine technology, partnerships, and insight to make business funding faster, more transparent, and more personalized.
FairSquare and its family of brands has been serving the small business community since 1999.
We have provided more than $3 billion in funding to over 50,000 customers to support their working capital and equipment financing needs.
We are one of the country's largest private providers of small business loans, having funded more than $3 billion to help small businesses grow.
Our personal approach helps strengthen small business owners and we pride ourselves on being a resource they can trust.
We are believers in small business owners.

Equal Opportunity

FairSquare is an Equal Opportunity Employer.