Siqi Chen is a prolific angel investor and the Co-Founder of Runway, the platform delivering financial data and insights in a language any startup founder can understand. 

We recently sat down with Siqi to explore how companies leverage personal video via tools like Windsor to elevate their marketing campaigns. He takes us through topics like: 

1. How automation paired with personalization drive outcomes
2. The evolution of eCommerce marketing and sales motions
3. Why Windsor’s AI-driven videos are the next frontier

“Windsor creates a way to cut through the noise and to actually grab and hold someone’s attention, giving companies an almost unfair advantage.” 

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Why generic marketing campaigns fail to drive growth

Like most of us who receive tons of unsolicited marketing messages every day, Siqi doesn’t hesitate to move those straight to spam. 

When you’re receiving so many inbound calls for your attention, your brain works in seconds to determine whether there’s true potential value and proof of work behind each message. 

It’s a pretty straightforward evaluation, since most of us already know exactly what to expect: 

• The copywriters plug in some basic details gathered through light research
• Then, they jump straight into automated or template sales messaging

There are blatant red flags and turn-offs, like when they address you by a job title you haven’t held in years because they’ve pulled your email off some database. 

On the other hand, you pause when you see a message that seems genuinely well-personalized to you as a recipient. And you’re more likely to entertain the thought of clicking or replying. 

In Siqi’s experience, he’s been most struck by the video messages he’s received, describing them as personal and valuable — even when he knows they’re ultimately marketing assets. 

With that, he’s amped to see existing video marketing functions at scale. Outbound marketing is a huge space, and the emergence of, for instance, mail merge for videos feels inevitable. 

The inevitability of AI-driven video automation

In Siqi’s words, salespeople are never going to stop doing their jobs. 

So, it becomes an arms race: Who’s gonna come out on top in cutting through the noise, grabbing consumers’ attention, and leveraging the right tech to help them do so? 

As AI and deep learning continue evolving, he affirms it’s inevitable that companies will want the cutting edge of marketing personalization tools in their arsenal. And video is that next frontier. 

Right now, it’s an arbitrage opportunity for companies using tech like Windsor. Soon, it’ll be table stakes, but it’ll never be some standard option for brands. 

From where he stands, video marketing will either be arbitrage or table stakes — full stop. 

“It’s going to be an arms race where, if you don’t have it, you’re just gonna get lost in the noise — just like what happened with mail merge and email.” 

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How early adopters can take advantage of email arbitrage

The first companies to master direct sales and growth marketing saw massive boosts compared to their competitors. 

Back then and today, early adopters who can wield new tech (and wield it well) will always have the upper hand. Siqi can provide countless examples across the industry and his own resumé. 

• Zynga — After Zynga developed for Facebook, multiple public companies emerged from that first wave. Those who came later, by and large, fell by the wayside. Siqi highlights how, quite simply, it’s hard to compete when network effects are already established. 
• Supercell — If you were early to mobile, you had a huge advantage in distribution. 
• Facebook — Facebook content and marketing are a given for brands today. Back then, it quickly became a hub for viral success; those who were first to it had a huge leg up. 

Overall, when there’s any new opportunity, platform, or piece of tech with promise and the capabilities to back it up, Siqi advises the strategy of experimentation and early adoption. 

Email: A universal channel that’s due for innovation

The longer Siqi works in industry, the clearer it becomes that email is here to stay. You’re not trying to navigate nitty-gritty sales over Twitter, Facebook, texts, etc. 

Email is how and where business gets done, and this likely won’t shift to a new channel anytime soon. All in all, it’s one of the most important platforms a B2B company has. 

• Siqi estimates that roughly 90% of any B2B company’s business comes from email. 
• Sales, growth, and marketing teams alike leverage email across roughly 20+ different use cases per function to drive revenue. 

“Today, email is table stakes in terms of how outreach is done. It’d be unusual to see a B2B company thrive without relying on email.”

The AI use case for effective personalization at scale

At face value, automation and personalization function as polar opposites, so it’s tricky to juggle both. The former enables scale while the latter drives conversion rates. 

However, to properly scale a B2B business, explains Siqi, you’ll have to figure out both levers. 

In performing outreach, you’ll have to be able to easily reach many people at once. Then, those outbounds need to be interested enough to respond. One without the other is suboptimal. 

As mentioned, it’s historically been difficult to strike that balance. For instance, the more media becomes mainstream, the less personalized it gets. Siqi points to the evolution of network TV. 

1. In the mid-1900s, there were only a few large networks like ABC and NBC. 
2. Over time, entertainment quickly became monopolized and homogenized. 
3. Now, with streaming, users can watch the precise shows they like while networks can reach everyone interested in those programs — personalization on both ends. 

The big takeaway? The success of personalization at scale is informed by high-quality tech. 

How personalization evolved through generations of tech

Depending on numerous factors, tech can handle automation and scale to varying degrees of success. For instance, if we look at the growth trajectory of pure software quality: 

• Mail merge — It’s one of the most basic email functions: taking addresses plus names, merging them, and sending tons of outbounds, marketing emails, etc. at once. 
• Data scraping — The next generation entailed scraping data and generating personalized emails from there. But, if the tech failed, the end result was off-putting to recipients. 
• AI — Today, scraping quality has improved and AI grows more and more accurate in customization. Personalization is stronger but hasn’t reached its total potential. 

In terms of where things go from here, Siqi views tooling like Windsor as the next generation of precise and effective personalization (driven by AI and deepfakes) at scale. 

As the pure tech only continues to improve, he imagines scenarios like placing an order from Amazon by chatting with a Jeff Bezos deepfake that’s delivering personalized product recs. 

“I think there’s currently still a dichotomy between scale and personalization. But, over time, impressive technology will be able to bridge that gap.” 

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Bridging the automation-personalization gap with Windsor

Siqi considers Windsor one of the first in a long line of platforms to come that’ll bridge the gap between automation and personalization. 

The end goal is creating personalized customer experiences at scale (meaning limitless growth potential) that are also indistinguishable from actual human service providers. 

This kind of tech would have the data comp abilities to know who you are, the products and media you like, and what you’d want to see. 

But the almost-human quality of top-notch personalization would be able to deliver on the next part: knowing what to say to make the sale. 

Ultimately, present-day AIs begin to fall apart when they just don’t know how to react or continue conversations like live humans do. 

From ​​Siqi’s perspective, Windsor is Version 1.0 as we build closer to that future. 

Why video messages trump text in marketing

Across standard sales campaigns, Siqi has witnessed massive jumps in engagement when shifting from text-based comms (i.e., “Hi, [Customer Name]”) to personalized video messages. 

Marketing teams have previously tried leveraging photo as the next step up from text, but static, auto-generated images get found out and overlooked pretty quickly. 

Meanwhile, personalized video, in Siqi’s words, can tap into something almost primal in the human brain that’s separate from reading text. 

At a basic level, text is a learned, upper-brain behavior, while looking at someone’s face, watching them speak your name, and hearing your name activates something close to the core. 

“Opening an email and hearing someone audibly call out your name — that grabs your attention immediately in a way that’s not possible with plain text.” 

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Why Siqi is betting on Windsor’s growth trajectory

When it comes to investing, Siqi focuses on a combination of: 

• The founder’s capabilities and character
• The market opportunity and industry macro trends
• The pure quality and growth trajectory of the product

Upon their first meeting, Windsor excelled on all of these fronts. Siqi describes: 

• Pranay’s (Windsor’s CEO) scrappy approach and background
• The immense potential of applying AI to a clear commercial need
• An emerging wave of AI-powered companies building tooling and SaaS

At a high level, he summarizes Windsor as translating advanced tech into something meaningful for the mainstream, delivering a ton of value and selling power across industries. 

Whenever new tech is on the precipice of entering the marketplace, Siqi asks himself: “If this works, how big could it become?” and “Can it realistically reach that level and scale?” 

He told us his answer when it came time to analyze Windsor as an investment: 

“If Windsor works and scales like I believe it can, it could change how everyone sells. And, yes, it’s totally feasible.”