January 7, 2025
January 7, 2025
Hollie Wegman has learned a lot about how companies grow, build and scale over the course of her career as a startup advisor. She applies that knowledge to help startup founders navigate every phase of often stellar growth, particularly in establishing and building out their brands.
“I’ve been there for the hard-won first $1 million in revenue all the way through to the filing of an S-1—and many other funding stages along the way,” she said.
Hollie has led marketing for Series A, B and C startups and more mature companies, such as Segment (former Mission North client and since acquired by Twilio), Envoy, MuleSoft, Salesforce and Cisco. These days, she advises Attio (CRM), Productboard (product management platform) and Sleuth.io (engineering efficiency platform).
“I’ve served as an interim CMO, COO and other executive roles while helping startups get through an important growth phase,” she said. “Founders at Series A have usually not hired executives. In my capacity as an advisor, I can give founders executive-level support in the time before they hire their exec team. I frequently advise on go-to-market issues and I can also be an extra pair of hands as they think about other functions such as recruiting, support or operations.”
With this wealth of expertise, we were excited to recently chat with Hollie over Zoom about startups, B2B marketing, the future of advertising, and other intriguing topics.
Are you hearing rumblings about what 2023 might be like?
There’s a lot of discussion of a downturn, and startups and VCs have been working together in 2022 to make sure companies have enough capital on board to weather the economic uncertainty. Many companies have enough runway to get through 2023 without taking more funding and it creates a really interesting space for innovation.
If we look at recession years, we see a counterintuitive spike in successful startups. Airbnb, Slack, Square and many more were founded in the last downturn. There is debate around why this is, but it seems as though the downturn pressure makes people more creative, more resourceful and more willing to take risks.
<split-lines>"Many companies have enough runway to get through 2023 without taking more funding and it creates a really interesting space for innovation."<split-lines>
How does B2B marketing change in a downturn?
Companies think it’s prudent to cut spending, and that can be correct. But, it’s also important to examine what’s happening in the market. If customers still have needs and budget to spend in your category and you cut marketing, you are just making space for your competitors to gain advantage. And it’s worth noting that Gartner is predicting SaaS spending to see an uptick this year and in 2023.
Specifically, how should communications change to help navigate in a downturn?
Communications programs provide a company with a huge opportunity to stand out during a downturn. When others are scaling back, you can reassure your customers that you are still there and still innovating. You can also gain advantage over your competitors at a time when they are possibly more quiet.
<split-lines>"Communications programs provide a company with a huge opportunity to stand out during a downturn. When others are scaling back, you can reassure your customers that you are still there and still innovating."<split-lines>
When they are quiet, does that represent an opportunity for everyone else?
Yes. You may finally have a moment of relative quiet in which to get your message out to the market after a noisy, multi-year tech cacophony!
What is next for retail and commerce?
COVID-19 completely changed the way we interact with retail because we were stuck at home and became more accustomed to the Amazon-type experience where you can have anything you want pretty much from billions of inventory. Now that consumers have returned, to an extent, to brick-and-mortar, you go into a store only to discover they no longer have that massive selection. Anyone who can fulfill the Amazon-type experience with technology has a huge opportunity.
<split-lines>"Anyone who can fulfill the Amazon-type experience with technology has a huge opportunity."<split-lines>
How would you describe the state of startups right now?
We’re in an astounding time in the history of technology and startups have more possibilities at their fingertips than ever before. A few years ago, AI, ML and crypto were buzzworthy, but we were still learning how these technologies would be used in our everyday lives.
Today, the likes of DALL.E, Deepfakes and Dogecoin are becoming mainstream. These evolutions are now powering more than just tech headlines, they are built into the software that we use every day. We can now build things that we could only previously imagine, which makes it an amazing time to be a startup.
What about marketing? What does the future look like in a world where there’s a 3D overlay on your phone or other devices?
We don’t want ads or marketing popping up everywhere. So, I think it will be a process of where the marketing community finds the right time and place.
I am also intrigued by the technologies that are fueling the future of advertising. I am specifically interested in the creator economy and how the people who create content on the internet are spawning the next generation of advertising.
Which technology areas most excite you, and why? Which area is changing the fastest?
I am fascinated by the future of programming, both low-code/no-code and augmented code. As a non-engineer in tech, the idea of more flexibility in what can be accomplished with less coding is alluring. Now there are even tools, like OpenAI Codex , that turn natural language into code. It’s pretty cool to imagine what is going to be possible for engineers and for the rest of us.
Tools such as Linear, Inner Table and Figma are design-centric instead of classic “function over form, form follows function.” It’s a completely different way of thinking. We don’t want these work software systems to feel like a prison when we are working from home or in the office. It should be more design-y and pleasurable, and it should work. It should be a beautiful, multiplayer experience.
