Jay Steinfeld is the Founder and former CEO of Blinds.com, the world's largest online retailer of window coverings, which was acquired by The Home Depot in 2014. Under his leadership, Blinds.com grew from a bootstrapped startup in his home to a billion-dollar enterprise, earning a reputation for innovation in e-commerce and technology-driven growth. Jay is also a Wall Street Journal best-selling author of Lead from the Core: The 4 Principles for Profit and Prosperity and the Entrepreneur in Residence at Rice University's Graduate School of Business, where he shares business insights.

Building a company is challenging, but building one that thrives without losing its soul is even harder. Leaders may talk about culture, growth, and decision-making, yet few manage to scale while keeping people engaged and energized. How can you create a business that grows sustainably, empowers employees, and thrives even after major transitions?

According to entrepreneur and leadership expert Jay Steinfeld, the answer lies in focusing on people and constant improvement. He emphasizes creating an environment where teams evolve continuously, experiment without fear of failure, and feel empowered to express ideas openly. Leaders should hire people who embrace change, reward contribution without artificial limits, and encourage constant reflection on daily improvements. By making thoughtful decisions despite incomplete information and designing systems that prioritize learning and growth, organizations can build enduring cultures.

In this episode of the Up Arrow Podcast, William Harris chats with Jay Steinfeld, Founder and former CEO of Blinds.com, about building a culture-driven company that scales effectively. Jay explains how personal challenges shaped his entrepreneurial mindset, the Four E's framework for company culture, and the partnership strategy that helped position his company for acquisition.

Jennifer Zick is the Founder and CEO of Authentic, a fractional CMO and marketing firm that helps businesses create scalable growth systems. With more than 25 years of experience in B2B marketing across startups, private equity–backed companies, and global organizations, she is a recognized leader in the fractional CMO space. Jennifer is also the Founder of LIFT Integrator Community™, an executive peer group for second-in-command leaders.

Marketing often starts as a flurry of activity — blog posts, ads, social media, campaigns. Yet many companies still struggle to see consistent growth from those efforts. Leaders invest more money and hire talented people, but results remain unpredictable and disconnected from revenue. Why does marketing feel chaotic in growing companies, and how can businesses transform it into a reliable growth engine?

According to marketing strategist Jennifer Zick, many organizations focus on tactical marketing through activities like content, campaigns, and lead generation without strategic alignment. Instead, leaders should elevate marketing to a strategic function that shapes decisions about positioning, pricing, market entry, and the customer experience. Jennifer recommends clarifying your ideal audience, defining why your brand matters to them, and building trust through consistent messaging across the entire customer journey. When marketing leaders collaborate closely with sales, operations, and finance, companies can align their strategy with measurable outcomes such as customer acquisition cost, retention, and lifetime value — turning scattered efforts into sustainable growth.

In this episode of the Up Arrow Podcast, William Harris sits down with Jennifer Zick, Founder and CEO of Authentic, to discuss how growing companies can move beyond tactical marketing and build strategic marketing leadership. Jennifer explains why random acts of marketing happen in scaling businesses, the difference between tactical "little-m" and strategic "big-M" marketing, and how fractional CMOs align marketing with revenue and long-term growth.

Jason Wong is the Founder and CEO of Paking Duck, which provides custom packaging solutions for DTC brands. Before launching Paking Duck, he built and scaled multiple DTC ventures, including Saucy, an end-to-end sourcing and logistics company, and the beauty brand Doe Lashes, which reached significant valuations under his leadership. Jason started his career as a teen entrepreneur in blogging, affiliate marketing, and e-commerce before expanding into international logistics, manufacturing, and supply chain operations.

Most founders obsess over ads, creative, and conversion rates — but overlook the one thing every customer physically touches. Packaging is often treated as a cost to minimize rather than an asset to optimize. How can the box on your customer's doorstep increase retention, reduce costs, and drive revenue?

Packaging manufacturing expert and e-commerce entrepreneur Jason Wong maintains that packaging can be a growth lever. He explains that packaging should be designed as a marketing channel inside the home — something customers proudly display, turning it into a mini billboard that keeps your brand top of mind. Jason advises founders to engineer packaging strategically by reducing dimensional weight to lower shipping costs, reinforcing structural integrity to prevent refunds and chargebacks, and designing with storytelling in mind to strengthen brand perception. When approached holistically, packaging moves from a backend expense to a compounding growth asset.

In this episode of the Up Arrow Podcast, William Harris sits down with Jason Wong, Founder and CEO of Paking Duck, to discuss how packaging drives e-commerce growth. Jason explains why packaging is a revenue driver, how smarter structural design reduces shipping costs and damage, and the common mistakes founders make when optimizing purely for cost.