Kevin Sisk, President of Bill360 | Episode 438

Cash flow shouldn’t depend on how many supplier portals your customers force you to use. We sit down with Bill360 president Kevin Sisk to unpack how true accounts receivable automation flips the script for small and midsize B2B companies, turning invoice chaos into a clean, controlled path to getting paid. Kevin’s journey from the Marine Corps through major processors and complex joint ventures to his first startup gives him a rare vantage point on why back-office change is hard and why now is the right time to make it stick.We break down the pain most owners know too well: dozens of buyer-driven AP systems, manual steps, scattered approvals, and aging invoices. Kevin explains how Bill360 couples AR software with embedded payment facilitation to remove handoffs and deliver one accountable partner. The result is faster payments, automated reminders and dispute handling, and a full audit trail even as teams change. We also explore why a B2B-first design matters, where live human support fits into a “light touch” platform, and how partnerships with vertical software vendors complete industry workflows without forcing users to switch systems.The conversation digs into the network effects that emerge when suppliers invite their buyers into a shared environment - suddenly the platform sees real relationships and behaviors instead of isolated transactions. That visibility powers smarter insights and, with AI, personalized recommendations that improve cash flow, reduce friction, and even execute actions with user consent. We zoom out to the broader payments landscape too: real-time rails, cross-border options, embedded finance and lending, and the rising need for security as fraudsters adopt AI. If you’re ready to reduce DSO, standardize invoicing, and bring clarity to collections, this episode is a blueprint for modernizing receivables without adding complexity.