Raymond Afara
@raymondafara
Executive product and GTM leader scaling AI-native commerce and payments.
United StatesWhat I'm looking for
I’m a visionary executive with over 15 years of experience building and scaling transformative commerce platforms, merchant solutions, and large-scale payment implementations. I consistently align product vision, engineering execution, and GTM strategy to maximize merchant revenue and drive enterprise value, while optimizing operational efficiency through hyper-growth and complex transitions.
At Skipify, I spearhead product and GTM strategy as EVP, Product & GTM, driving platform adoption across enterprise merchants, issuers, and global PSPs. I partner directly with the CEO to architect strategic roadmaps, build revenue forecasting models, and ensure platform scalability—while navigating organizational transitions to preserve runway and maximize efficiency.
Previously at Stripe, I led Payments Practices for the Americas, architecting and launching Stripe’s global payments best-practice framework to reduce merchant friction and accelerate integration efficiency. I also built and scaled a highly technical GTM enablement engine that increased technical sales velocity and enterprise implementation success rates, and I founded Stripe’s inaugural Integration Specialist team as a global center of excellence.
Earlier at Adyen, I drove global operational scalability by launching automation initiatives that eradicated configuration-related support tickets by 90%, supporting multi–billion dollar transaction volume growth. I also led enterprise implementations that delivered an 181% YoY increase in go-lives, and I continue to bring a solutions-first mindset from roles including Senior Solutions Architect / Implementation Engineer and CoFounder & CTO.
Experience
Work history, roles, and key accomplishments
EVP, Product & GTM
Skipify
Jan 2025 - Present (1 year 6 months)
Spearheads product and go-to-market strategy to drive platform adoption across enterprise merchants, issuers, and global PSPs. Partners with the CEO on roadmaps, revenue forecasting, and platform scalability while leading strategic partnerships.
VP, Product & Customer Experience
Skipify
Jan 2024 - Jan 2025 (1 year)
Owned product strategy, advancing shopper recognition to 60%+ and improving merchant checkout conversion by 9%. Led merchant experience, implementation, and support teams with top-quartile NPS and retention.
VP, Implementation and Support
Skipify
Jan 2023 - Jan 2024 (1 year)
Slashed enterprise onboarding timelines by 73% through process automation and operational workflow optimization. Built operational KPIs, health dashboards, and merchant self-service tools to improve visibility into account health and expansion opportunities.
Architected and launched Stripe’s global payments best practice framework to reduce merchant friction and accelerate integration efficiency. Built and scaled a GTM enablement engine to increase technical sales velocity and enterprise implementation success rates.
Led global automation initiatives that eliminated configuration-related support tickets by 90%, improving operational efficiency. Scaled operations infrastructure and process standardization to support multi-billion dollar transaction volume growth.
Directed implementations for enterprise clients (including McDonald’s, Subway, GAP, Etsy, and SeatGeek), driving a 181% YoY increase in go-lives. Influenced product roadmap based on merchant feedback and led merchant education programs and thought-leadership workshops.
Delivered end-to-end technical integrations across global eCommerce, POS, and platform environments for Fortune 500 merchants. Joined as an early U.S./NYC hire and helped establish Adyen’s North American footprint.
CoFounder & CTO
Panadoora Point of Sale
Jan 2015 - Jan 2016 (1 year)
Co-founded Panadoora Point of Sale and served as CTO.
Salesforce SFDC Instructor
Montreal College of Information Technology
Jan 2015 - Jan 2016 (1 year)
Served as a Salesforce SFDC instructor at the Montreal College of Information Technology.
Software Engineering Manager
Azur Group
Jan 2014 - Jan 2016 (2 years)
Managed software engineering activities as a Software Engineering Manager at Azur Group.
Software Engineer roles
Oralys Inc
Jan 2010 - Jan 2014 (4 years)
Worked in software engineering roles for Oralys Inc.
Software Engineer roles
International Air Transport Association
Jan 2010 - Jan 2014 (4 years)
Worked in software engineering roles for International Air Transport Association.
Founded Stripe’s inaugural Integration Specialist team and established it as a center of excellence for solution design and payments optimization. Instituted presales collaborative processes across GTM, product, and engineering to improve merchant activation.
Education
Degrees, certifications, and relevant coursework
Raymond hasn't added their education
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Tech stack
Software and tools used professionally
Availability
Location
United StatesAuthorized to work in
Job categories
Skills
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