Who is Aiwyn and what do we do?

Aiwyn is transforming the way accounting firms manage the entire revenue lifecycle. Backed by top-tier investors like Bessemer, KKR, and Revolution, we’re one of the fastest-growing scale-up SaaS companies in the world. We build category-defining technology—and we’re doing it with world-class people, processes, and products.

Role Overview:

Aiwyn is seeking a Technical Payment Operations Specialist to drive the efficient execution, monitoring, and optimization of our payment systems and processes. In this role, you’ll play a critical part in managing our For Benefit Of (FBO) model for ACH processing, ensuring accurate and timely bank reporting, and maintaining strict compliance with Anti-Money Laundering (AML) regulations.

You’ll combine technical expertise, operational rigor, and regulatory awareness to enhance the reliability and scalability of Aiwyn’s payment infrastructure. As a member of a fast-paced startup, you won’t just operate the system—you’ll improve it.

You’ll help design and document the playbooks and processes that make operational excellence repeatable and sustainable. You’ll also partner with cross-functional teams to anticipate capacity needs, support growth, and ensure that our payments ecosystem runs smoothly and securely.

What will your day-to-day responsibilities look like?

Manage and oversee Aiwyn’s FBO model for ACH processing, ensuring accurate settlement, reconciliation, and reporting.
Partner with banking institutions to coordinate daily and monthly reporting on transactions, balances, and exceptions.
Monitor payment flows across ACH, credit card, and alternative payment methods, identifying and resolving operational discrepancies.
Ensure compliance with internal policies, payment industry regulations, and security standards.
Collaborate with technology teams to configure, maintain, and optimize payment processing systems.
Work with APIs, payment gateways, and integrations to troubleshoot issues and enhance performance.
Partner with Product and Engineering teams to support new payment feature rollouts and system enhancements.
Analyze transaction data to uncover trends, inefficiencies, and potential risks.
Develop and deliver regular reports on payment operations metrics and KPIs.
Provide data-driven insights that guide operational improvements and enhance the customer experience.
Serve as the first line of technical support for payment-related issues, resolving or escalating as needed.
Coordinate with vendors, financial institutions, and internal stakeholders to address and resolve escalated matters.
Identify and implement automation opportunities to streamline payment workflows and improve efficiency.
Develop and document operational procedures to ensure consistency, scalability, and compliance across teams.

What You’ll Bring:

3 + years of experience in payment operations, fintech, or banking operations roles.
Direct experience with ACH processing, FBO models, and AML compliance preferred.
Strong understanding of ACH processing flows and FBO account structures.
Proficiency in bank reporting, reconciliation, and settlement operations.
Knowledge of AML, KYC, OFAC, PCI DSS, and NACHA compliance requirements.
Familiarity with accounting and reconciliation principles.
Accredited ACH Professional (AAP) NACHA qualification preferred.
Bachelor’s degree in Finance, Information Systems, Computer Science, or a related field.

Soft Skills & Mindset

Naturally curious — you dig deeper when something doesn’t work as expected.
Strong analytical and problem-solving abilities with meticulous attention to detail.
Excellent communication and collaboration skills for working with technical, banking, and compliance stakeholders.
Ability to work independently while partnering effectively across teams in a fast-paced environment.
A proactive mindset with a passion for operational accuracy and continuous improvement.

Benefits and Perks

The big-picture value proposition of this role is simple: join us, and you'll be paid competitively to have freedom in solving worthwhile, challenging problems alongside other A-players at a fast growing SaaS startup led by an experienced and successful co-founding team with industry experience.
Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year. We encourage our team to recharge and explore the world beyond their home office walls.
Remote, work-from-anywhere culture
Flexible PTO
World Class health benefits - we believe in fostering flourishing teams by providing benefits that go beyond the usual standards - Health, vision, dental, HSA/FSA, and mental health support.
Stock options - every Full Time Employee has ownership in Aiwyn's future and success.
401(k) matching

Our Values:

Trust - We champion transparency, welcome differing perspectives, uphold accountability, and trust that others have good intentions
Courage - We have the courage to take calculated risks and embrace change, knowing what worked in the past won’t always work in the future
Impact - Rooted in determination and innovation, we chase extraordinary outcomes and impactful results
Relentlessness - We approach challenges with an unwavering resolve, never settling for mediocrity, and always striving to surpass expectations