2021 — present
Co-Founder & CEO
Alvin Technologies
Building AI-native enterprise software for coordinated operational execution.
About
I've spent my career moving between building, investing and operating early stage ventures.
I'm Winston Reid, a Chicago-born product strategist and operator. My work has taken me across the United States and Africa — from venture investing in Morocco, to payments at Paystack in Nigeria, to leading product teams in Nairobi and building AI-enabled operational software.
Background
A product career shaped by markets, not just software.
I started on the commercial and capital side of startups, working directly with private-company CEOs and later evaluating early-stage technology companies as a venture investor.
That pulled me deeper into product. At Paystack I worked on core payments and international expansion. At Lynk and Orbitt I served as Head of Product, translating messy company priorities into products, systems and engineering execution.
Today I lead product through Alvin Technologies and selectively work with founders, investors and technology teams on product strategy, AI-native systems and complex execution — turning ambiguous business problems into clear product direction and software that actually ships.
AFIS · Expert panelistLomé, Togo · 2023
Experience
2020 — 2021
Head of Product · Part-time consultant
Orbitt
Led product strategy and engineering delivery in a part-time senior consulting engagement, bringing an integrated trade-finance marketplace from concept to launch.
2019 — 2020
Head of Product
Lynk
Led Product, Product Design and Engineering for a multi-sided marketplace.
2018 — 2019
Product Manager — Core Payments & International Expansion
Paystack
Improved payment performance and shipped a new checkout experience at one of Africa's defining fintech companies.
2017 — 2018
Director of Investments
Outlierz Ventures
Evaluated 1,000+ technology startups and contributed to the firm's first investments.