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.

Expertise

Product strategy
Growth strategy
Direct to consumer (DTC)
B2B Saas
Subscription & retention
Paid acquisition
Stack selection & vendor evaluation
AI

How can Justin help you?

AI-Native Workflow Audit

Bring an AI workflow you're building — a content engine, a research agent, a customer ops automation, a prompt library, an in-house tool — and we'll teardown what's working, what's leaking quality, and which primitives to swap. You'll leave

Growth Model Diagnostic

A working session to find what's actually broken in your growth model — paid efficiency, retention, offer architecture, funnel, onboarding — and rank what to fix first. Works for DTC, B2B SaaS, or subscription. Bring numbers, leave with a p

Stack & Team-Shape Decision

For founders and operators rethinking their stack or org chart in the AI shift. Bring the specific decision: which tools to consolidate, which to swap, what role to open next, what to keep in-house vs. compose from primitives. We'll work it

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.

Booking policy

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What is the policy for mentor cancellations or no-shows?

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What if my mentor doesn't accept my request?

Is there a grace period for session overflows?

Code of Conduct

No Pitching

Privacy and Confidentiality

Professionalism

From$216/ session

Justin Winter

AI-forward, product-minded growth leader & founder

How can Justin help you?

AI-Native Workflow Audit

Growth Model Diagnostic

Stack & Team-Shape Decision

Who is this for?

Experience

VP of Growth

VP of Growth

Head of Cloud Product

Head of Marketing, Airshop

CEO, Pendleton Places

Co-founder & CEO, Boostopia

Co-founder & CEO, Diamond Candles

Booking policy

What is your cancellation policy?

What is the policy for mentor cancellations or no-shows?

What's your refund policy?

What if my mentor doesn't accept my request?

Is there a grace period for session overflows?

Code of Conduct

No Pitching

Privacy and Confidentiality

Professionalism

From $216· Mentoring Session Instant Booking