Justin Winter
VP of Growth | Digital Product & DTC Ecom Executive | Consumer Brands
About
I'm a digital product and growth executive operating at the intersection of ecommerce, subscription systems, and margin-first revenue design. Currently VP of Growth at A Pup Above, where I own the digital product roadmap and full-funnel growth engine across DTC and Amazon — building subscription programs, conversion infrastructure, and analytics systems tied to CAC payback and LTV expansion. Previously led growth and GTM at Swiftly (retail media SaaS), headed cloud product at Legacybox (2.9PB+ consumer media platform), and built DTC from scratch as Head of Growth at LonoLife. Earlier, I co-founded Diamond Candles and scaled it to $22M+ through performance marketing and retention systems, and founded Boostopia (CX SaaS) serving brands like Allbirds and Bombas. My focus: unified product + growth operating systems where acquisition, retention, and margin discipline reinforce each other. I work best with consumer brands at $5M–$100M building durable digital revenue engines. Reach out for feedback on DTC strategy, subscription economics, ecom architecture, or offer design. prev./current consulting, advisor, investor: boll & branch pura vida mosi tea cora sumall itzy ritzy soapbox oncotect blue core the pour over rockflowerpaper bare bones broth
Experience
Head of Marketing, Airshop
As the Head of Marketing at airshop, an innovative online beauty and cosmetics retailer, I spearheaded a multifaceted digital marketing strategy during our critical product-market fit phase. Joining as the second full-time employee post-founders, my role was pivotal in establishing and expanding our market presence, ultimately contributing to the company’s recognition and backing by notable investors, including Shopify. Airshop, a dynamic spin-out from Deliverr—a fast-growing startup recently acquired by Shopify—has rapidly carved a niche in the beauty industry. My expertise encompasses leading comprehensive digital advertising campaigns across a variety of social platforms, including Meta, TikTok, Snapchat, Google, and YouTube. By orchestrating daily operations and steering our strategic direction, I aimed to align our marketing efforts closely with the company's overarching goals. Managing creative and advertising agencies, I led the development of compelling creative strategies that resonated with our target audience, driving engagement and conversions. Collaboration with product teams was key to sourcing, implementing, and managing best-in-class tooling for customer insights, research, and retention marketing. My leadership in the integration and strategic utilization of Klaviyo, for instance, streamlined our email marketing efforts, enhancing customer retention and engagement. I also played a critical role in amplifying our email capture mechanisms and leveraging Shopify apps to reduce the development load on our in-house product and engineering teams, ensuring a seamless and efficient operational workflow. My tenure at airshop was marked by a hands-on approach to digital marketing, from the granular details of campaign management to the high-level strategy that drives brand growth.
CEO, Pendleton Places
We specialize in managing properties for other investors nationwide, focusing on maximizing their returns through short-term rental operations. Located in Durham, NC, we cater to guests seeking accommodations ranging from a few nights to several months. Our portfolio includes value-oriented single-bedroom apartments, premium downtown condos, and spacious single-family residences suitable for families and larger groups. As a dedicated property management company, we offer comprehensive services to property owners. Our expertise lies in transforming their investments into profitable short-term rentals. We no longer lease properties directly; instead, we focus solely on managing and optimizing properties for our clients. Our property management solutions are designed to assist owners in either enhancing their current short-term rental offerings or venturing into the short-term rental market for the first time. We provide expert guidance on design, furnishing, and marketing strategies to ensure a successful rental operation. We pride ourselves on frequent property inspections to address preventative maintenance promptly, reducing the risk of significant repairs and expenses. Our commitment to property upkeep and our financial alignment with property owners' interests underscore our dedication to minimizing the hassles and costs associated with tenant turnover, ensuring a seamless and profitable investment experience for our clients.
Co-founder & CEO, Boostopia
As CEO and Co-Founder of Boostopia, I led the company from its inception to pivot, focusing on enhancing customer support operations beyond traditional help desks like Zendesk and Gorgias. We aimed to fill a market gap with a platform that improves team efficiency and customer experiences. Boostopia partnered with brands like Allbirds and over 100 other DTC and e-commerce brands, gaining insights into support challenges and opportunities from startups to established companies with 100+ person teams. Our work emphasized the importance of strategic support operations in growing businesses. We secured angel funding from Jason Calacanis, validating our vision and potential. Despite reaching $25k in MRR and finding product-market fit, scaling challenges led to the company's closure. This decision allowed the team to pursue new opportunities, applying lessons learned. My time at Boostopia highlighted the importance of resilience, innovation, and a commitment to improving customer support and operations.
Owner, Longer Table Holdings
We are a family holding company that starts, buys, and manages real estate, direct-to-consumer brands, professional services, and software businesses. We reject any cultural mandate that requires exploitive business practices whether that be towards our employees, customers, or our community. We seek to do no harm, keep the rules, play fair, solve problems, and add value; particularly current or historically under-resourced or under-represented populations. Ultimately, we desire creative restoration through sacrifice — to bless others, renew culture, and give of ourselves.
Co-founder & CEO, Diamond Candles
Diamond Candles logo Co-founder & CEOCo-founder & CEO Diamond Candles · Full-timeDiamond Candles · Full-time Jan 2011 - Feb 2016 · 5 yrs 2 mosJan 2011 - Feb 2016 · 5 yrs 2 mos Durham, NC · On-siteDurham, NC · On-site As Co-founder & CEO of Diamond Candles, from Jan 2011 to Feb 2016, I led the brand to become the fastest-growing and largest online home fragrance company globally. My role encompassed guiding the company through strategic growth, acquisition, retention, and product innovation, focusing on establishing a modern, dynamic home fragrance brand. I managed a multifaceted team of over 50 professionals across manufacturing, customer service, creative, and growth departments. Under my leadership, we implemented innovative viral organic digital growth strategies, notably scaling our Facebook page to over 1 million fans. This pioneering approach to digital marketing fueled hyper-profitable growth, with the company achieving over $1M in revenue in our first year, and subsequently reaching milestones of $5M, $15M, and peaking at $22M in annual revenue. Throughout my tenure, I worked closely with private equity firms to navigate the acquisition evaluation process. While several opportunities to sell the company were considered, a sale was ultimately not finalized. Instead, I was bought out by my partners, who continue to manage the company to this day, leaving me with no active connection or involvement. This journey with Diamond Candles not only underscores my capability to drive significant business growth but also reflects my strategic acumen in evaluating and making pivotal business decisions. My experience with the brand exemplifies a commitment to innovation, leadership, and the successful scaling of a company in the competitive online retail space. Managed a team of more than 50 people across manufacturing, customer service, creative, and growth related roles.