Justin Winter
AI-forward, product-minded growth leader & founder
Composes AI-native growth and product systems across Consumer, B2B, SaaS, and retail media — not a one-channel specialist. Bootstrapped a $50M consumer brand at 22 yrs old.
How can Justin help you?
Who is this for?
Product leaders
Founders
Growth leaders
Justin Winter’s Biography
I'm a digital product and growth executive operating at the intersection of ecommerce, subscription systems, and margin-first revenue design. Across the last decade I've co-founded a $50M+ DTC brand (Diamond Candles) at 22 yrs old, built a B2B SaaS to product-market fit with Allbirds and Bombas as customers (Boostopia), led product on a 2.9PB+ consumer media platform (Legacybox), built DTC from scratch (LonoLife), ran growth at a retail media SaaS (Swiftly), and currently own the digital product roadmap and growth engine at A Pup Above. The throughline isn't a vertical — it's a unified operating system where acquisition, retention, and margin discipline reinforce each other instead of competing for budget. Advisor and investor work across consumer brands and tech, currently and previously: Boll & Branch, Pura Vida, Bluecore, Cora, Itzy Ritzy, SoapBox, Mosi Tea, SumAll, Oncotect, The Pour Over, Rockflowerpaper, Bare Bones Broth. Reach out for honest feedback on DTC strategy, subscription economics, ecommerce architecture, or offer design. Bring numbers and a specific decision — I'll show up ready to work it.
Experience
VP of Growth
A Pup Above Dog Food · Feb 2026 – Present
Own the digital product roadmap and full-funnel growth engine across DTC and Amazon for a premium subscription dog food brand on Shopify Plus. Lead acquisition, lifecycle, retention, offer architecture, and analytics infrastructure tied to CAC payback and LTV expansion. Shipping AI-native workflows with Anthropic, Claude, and Cursor as core primitives in the daily stack.
VP of Growth
Swiftly · Jun 2025 – Feb 2026
Led go-to-market and demand generation at Swiftly, a $1B+ valuation unicorn retail media SaaS platform backed by significant venture capital. Owned paid media, outbound, and product-led acquisition across both sides of the marketplace — retailers and brand advertisers. Aligned marketing, sales, and product around a shared revenue motion.
Head of Cloud Product
Legacybox · Jan 2025 – Apr 2025
Led product for Legacybox's consumer cloud platform — a 2.9PB+ digital media archive that digitizes and preserves physical photos, film, and tapes for hundreds of thousands of US households. Owned the digital product roadmap spanning ingestion, storage, search, and the customer-facing experience that turned a one-time digitization purchase into a long-term recurring relationship. Worked across engineering, ops, and growth to compose the stack — what to build in-house, what to compose from cloud
Head of Marketing, Airshop
Sep 2022 – Feb 2024
Head of Marketing at airshop, a Shopify-backed beauty discovery commerce platform that raised $5M+ in seed funding after spinning out of Deliverr. Joined as the second full-time hire post-founders and built the digital marketing function from zero — paid media across Meta, TikTok, Snapchat, Google, and YouTube, plus Klaviyo lifecycle and the Shopify app stack. Owned creative direction, agency management, and the customer insights tooling that supported product-market fit.
CEO, Pendleton Places
Jan 2021 – Aug 2023
Acquired and scaled a wholly-owned property management company in Durham, NC focused on short-term rental operations for absentee investors. Manages a portfolio ranging from single-bedroom apartments to family-scale homes nationwide. Aligns operationally with property owners on optimization, design, and preventative maintenance rather than direct leasing.
Co-founder & CEO, Boostopia
Jun 2016 – Jun 2021
Co-founded and led Boostopia, a primarily bootstrapped B2B SaaS focused on customer support operations beyond traditional help desks like Zendesk and Gorgias. Reached $300K+ ARR and product-market fit with Allbirds and 100+ other DTC brands as customers, with angel funding from Jason Calacanis. Hit a scaling wall and wound the company down — the team moved on with a sharper read on what makes support tooling defensible vs. commoditized.
Co-founder & CEO, Diamond Candles
Diamond Candles · Jan 2011 – Feb 2016
Co-founded and led Diamond Candles to $50M+ in cumulative revenue across five years as the largest online home fragrance brand globally. Built the team to 50+ across manufacturing, CX, creative, and growth, and pioneered viral organic Facebook growth that took the page past 1M fans before paid social was a real channel. Evaluated multiple acquisition processes with PE before being bought out by my co-founders.
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