Payments industry leader with 12+ years in merchant services and ISO and ISV payments, sourcing, negotiating, and shipping product and technology partnerships end to end. Now I orchestrate AI products, researching the friction, designing the agent, and pressure-testing it before a real user is at risk.
About
I'm Calvin Riley, a payments industry leader with 12+ years leading complex product and technology partnerships end to end in merchant services and ISO and ISV payments. I source, evaluate, negotiate, and secure partnerships aligned with company priorities, structure agreements that balance partner needs with product objectives, and own the integration experience all the way through measured adoption. I'm trusted across C-suite, product, engineering, finance, and legal — the connective tissue that gets cross-functional deals done.
I now turn that operator's instinct toward building AI products. As an MBA candidate in Applied AI at Northwest University, I research the friction, decompose the workflow, design the agent, and validate it with synthetic personas and real testers before shipping. I move fast, pressure-test ideas against real-world viability, and care more about shipping something that works than sounding impressive. The portfolio below is the proof of work.
Selected AI work
Founder · Product, AI & Go-to-market · 2026
A website plus a 24/7 AI front desk for small service businesses. It answers every call, books appointments, transfers to the owner when needed, and gives each owner their own My Front Desk dashboard of calls, calendar and settings. Setup after payment is fully automatic: number provisioning, onboarding and the shop's AI agent. Built on Retell voice AI, Vercel and Stripe.
Visit CascadeAnswer → PrototypeFounder · Product & AI orchestration · 2026
A deployed AI agent that meets high-functioning, "successful-but-empty" professionals where they are, runs a clinically-informed discovery conversation, and surfaces the belief patterns driving their discontent. Built on Claude with a clinical-psychologist co-founder's framework, validated with synthetic personas and human testers, and engineered with deterministic safety guardrails. 4/4 patterns classified correctly · 0 false negatives on crisis signals.
Read the full case study → Case studyFounder · Orchestrator & Payments Agent
A multi-agent AI system that gives a single landlord the operating capacity of a full property-management company. I lead the team and own the Payments Agent, with Fair Housing stewardship designed in.
Read the full case study → Case studyBuilder & Product Owner · Sales intelligence
An agentic sales-intelligence engine I built for my Equinox Payments team — it validates real product-fit, then scores every prospect by ecosystem leverage across the payments supply chain.
Read the full case study →Experience
Director of Sales · Product Partnerships & Channel
Lead product and technology partnerships across North American enterprise merchants, software companies, and resellers — owning strategy, sourcing, deal leadership, and the integration experience for the Voyager platform, Luxe terminal line, and HUB estate-management suite.
Independent Sales Organization (ISO) · Owner-Operator Concurrent
Own and operate an independent commerce book — originating and managing accounts including Canadian and cross-border merchants, with POS and software integrations and direct rate and commercial-term negotiation.
Strategic Partnerships Director
Owned the full product-partnerships lifecycle — sourcing, evaluation, negotiation, structuring, integration, and adoption — across software companies, merchants, and the broader commerce ecosystem.
Senior Level Account Executive
Focused on ISV and channel partnerships, product launches, and partner strategy.
National Director of Sales and Business Development
Built and managed the product-partnership and ISV program, sourcing software partners, structuring integration scope, and owning the adoption experience. Managed a reseller team of more than 22.
Jr. Sales Director
Started as an independent reseller, selling door-to-door and business-to-business, and reached a $25,000 sales margin in the first three months.
Key competencies
Education & ventures
Northwest University · In Progress
Focused on researching and building applied-AI strategy — the academic backbone behind the portfolio work.
San Francisco State University
A media-and-business foundation that still shows up in how I communicate, position, and tell a product's story.
Full Sail University · 2013 to 2015
Daily operator across LLM-based agents, agentic workflows, and automation frameworks as operational tools — API integrations, prompt engineering, and AI-human collaboration patterns.
Co-founding The Meridian, a faith-based life-alignment platform, and CascadeAnswer, a 24/7 AI front desk for small service businesses. Also building AI-powered business tools that turn emerging technology into working products.
Beyond work
20+ years as a DJ and creative director — from Santa Barbara residencies to festivals and a San Francisco radio show. Still performing the occasional set to stay close to the craft.
Husband and father of two in Camas, Washington. My wife is a doctor. Our son Cal plays football and is transitioning to baseball, and our three-year-old daughter does ballet and swimming. I'm a sports enthusiast, and I'm at church every Sunday.