Why We Invested in Retail Zipline

Dan Wenhold
4 min readMar 2, 2021


Streamlining communications in the retail industry may be just the beginning

Image Credits: Fabio Bracht/Unsplash

Zipline helps retailers improve workforce management and communications between corporate decision makers and store employees. As a result, retailers boost accountability, transparency, and employee engagement across distributed teams.

Communicating at scale in any industry can be challenging and this is especially true in the world of retail. A brand’s corporate headquarters might be located in San Francisco, but it could also operate 100+ brick-and-mortar stores across the globe. Flawless communication is required in order to successfully bring retail brands to life in physical stores. I know this firsthand from my background in retail — prior to Fifth Wall I served as the Director of Retail at an omnichannel brand, The Black Tux. While there, I was tasked with building out the company’s brick-and-mortar retail footprint while also managing operations across an increasingly distributed workforce. Melissa Wong, Zipline’s Co-Founder & CEO, also experienced this challenge for more than 10 years in her prior role in corporate communications at Gap, Inc. and Old Navy. In that role, she was responsible for maintaining brand quality from HQ across a disparate network of stores. Based on this experience, it was clear to her that the breakdown of store execution — and potential damage to a brand — can result from ineffective communication. As a result, Zipline was born.

For many years, retail and many other Built World industries have attempted mass communication to a distributed workforce through a cobbled-together collection of emails, portals, bulletin boards, Slack, SharePoint, and other ineffective tools. It was inevitable that this cumbersome approach would not be sustainable, and over the past year, it was put to the test. As store closures, remote work, and distributed workforces have become the norm, Zipline’s solution has consistently been ahead of these trends, and as a result, has become an even more powerful tool to help ensure clear, consistent, and effective communications.

In 2014, Melissa and her co-founder, Jeremy Baker (who now serves at Zipline’s CTO), envisioned streamlined communications between headquarters and the field, ultimately leading to better store execution and more profitable sales. Today, Zipline is at work in more than 17,500 stores — such as BevMo!, L.L.Bean, Sephora, and TOMS — helping approximately 270,000 users communicate more effectively.

Fifth Wall’s Path to Zipline

With approximately $1.3 billion in commitments and capital under management, we aim to offer our corporate strategic partners — some of the world’s largest and most influential real estate corporations — access to new technology, a finger on the pulse of the future, and solutions to their biggest challenges. When speaking with these partners, we discovered that many of them struggled to manage communications from HQ to the field level, especially among those managing retail employees, brokers, leasing agents, and other types of field workers.

I was familiar with Zipline and immediately made a connection with Melissa as a result of our shared experiences working as retail operators. She struck me as a founder who didn’t simply have an epiphany from arm’s length — she dealt with these communications challenges personally on a daily basis over the course of her 10+ years at Gap, Inc. and Old Navy. Her passion to solve for something that was deeply personal to her based on past professional experiences was apparent. She understands the customer and has an intimate awareness of how culture varies from employees at HQ to working in the retail stores. This unique perspective, coupled with her co-founder’s tech prowess, yielded the thoughtful and effective product development of the Zipline platform.

Under Melissa’s leadership, Zipline has more than doubled its revenue every year since launch, despite significant pandemic headwinds in 2020. Melissa’s strong emotional intelligence and empathy for the customer has enabled her to successfully build a widely-distributed and remote team, long before the pandemic normalized this model of working.

Synergies Abound for Fifth Wall LPs and Zipline

The Fifth Wall network is rich with opportunities for Zipline to explore potential partnerships among our retail-focused partners and portfolio companies. However, we believe retail to be just the beginning for Zipline as we envision the product appealing to many Built World industries. The opportunity for Zipline within real estate could lie with organizations whose HQ office must communicate daily with field operations workers, such as more traditional brokers with a geographic focus (e.g., CBRE, Cushman & Wakefield), leasing agents within multifamily and SFR (e.g., Equity Residential, Greystar), or construction site workers.

Regardless of industry, once in place, Zipline offers a multitude of approaches for an organization to rethink communications. Fifth Wall believes that Zipline could ultimately expand and become the software platform of record not only for communications, but also for all people management functions, such as scheduling and payroll. As the Zipline team drives to become a mission-critical software for every organization with field operations employees, we’re excited to fund their momentum and partner with Melissa and her team along the way.

Forward-looking statements and opinions as to real estate markets or any other matters, as expressed in this presentation, are those of the individual presenters, but are not necessarily the views of Fifth Wall as a firm, and cannot constitute a guarantee of future success or profitable results. As a result, investors should not rely on such forward-looking statements and/or opinions, or on anything else contained in this video, in making their investment decisions.

The information discussed above is presented solely for informational purposes and should not be interpreted as an offer or recommendation to buy or sell securities.



Dan Wenhold

Partner at Fifth Wall Ventures investing in built world technology. Previously: The Black Tux, Battery Ventures, Baird & Univ. of IL @ U-C.