As a PMM charged with balancing both self-serve and enterprise customers of the same product, what are the nuances between the two?

You have a very tall order ahead of you! These two motions aren't nuanced differences -- they are completely different playbooks. Most of my AMA questions are about comparing the two, so I'll summarize the key differences here:

The buyer

• Often a self-serve buyer is a team lead/director level or an end-user, looking to try out the product to see if it could work for themselves or their team. They are rarely thinking about their entire company's needs. These buyers want to validate the product fast and implement it even faster because it promises to solve an issue they are facing right then and there. They care about quick-time-value, self-driven learning & documentation, community support, and ease of setup.

• An enterprise buyer is thinking about the opposite. They are looking for solutions to organizational challenges they are facing now and long into the future. They are often willing to: spend more time vetting all the best solutions through RFPs etc.; to pay for someone else to configure and manage the product; and they care deeply about customer service, not just product experience. Their decision has more lasting implications, like dealing with procurement, a task that no one takes lightly ;)

The buyer journey

• A PMM building a self-serve buyer journey connects the top of the funnel through to product and everything in between. You only have seconds to tell a compelling story and the feedback you get is a mix of data insights and customer responses.

• An Enterprise buyer journey has to take into account human interaction as a content delivery vehicle. There are more direct feedback loops and more room for robust and detailed storytelling.

The tactics

• Self-serve marketing activities will include paid marketing campaigns, website optimizations, SEO content & blogs, Youtube, PR, online community engagement etc. all focused on driving traffic and signs ups.

• Enterprise activities are most focused on that human touch through events, analyst relations, sales, channel, webinars etc. all focused on driving pipeline.

Great question—thanks for asking!

One thing to get out of the way first: Most products will have both users and buyers and those users and buyers can live across self-serve and enterprise.

Users: Individuals that get value from your product (either actively or passively) but don’t have the power or need to purchase.

Buyers: Get value from your product and also have the power to purchase–buyers can exist both in self-serve and enterprise plans.

Now to get into the nuances… Customers, no matter whether they live in self-serve or enterprise, need to be led to value in your product, it’s really their needs that differ.

Self-serve customers typically have less complex needs. Perhaps they have a smaller team or fewer security or setup requirements. They could even just be using simpler versions of your product! Their needs can be delivered on with a hands-off product-led approach.

Enterprise customers have more complex needs—whether that be the need to manage thousands of users, integrate with their tech stack, or if their using products that require a hands-on setup and success process. There should be significant, incremental value of having an account team in order to support them. It’s critical that the move to Enterprise financially makes sense—the company should deliver enough incremental value to the customer so they are willing to pay a higher price point that covers and exceeds the additional overhead required to service them.

I know this situation well; it's the same here at Klaviyo! 

First, you need to understand the composition of both audiences. Are the self-serve customers smaller businesses that don't need to talk to sales to feel comfortable using the product? Are at least some of them actually enterprise customers poking around in the product before they talk to sales? Is this a product-led company that makes it easy for end users at enterprise companies to self-serve? Maybe a combination of the above? 

With that in mind, there are some core differences and some potential differences. 

The core differences:

•  The buyer journey. Self-serve customers usually don't have long and complex evaluation processes with lots of different stakeholders. Enterprise customers usually have long sales cycles involving multiple different stakeholders. Serving both audiences means you need to invest in both self-serve content (mostly via your website) and sales enablement (pitch decks, one-pagers, training on personas and competitors and objection-handling, etc.).
•  The onboarding and value-realization process. Self-serve customers need an intuitive, self-driven onboarding flow that helps them not only learn how to use the product, but also realize value very quickly. There's no one holding their hand as they get up to speed, so they can easily drop off (and it's hard to win them back). Don't forget that the onboarding experience is both inside and outside of the product. Meanwhile, enterprise customers generally have more complex and resource-intensive onboarding and implementation journeys, usually led by Customer Success and/or Solutions Architect teams. There's still the potential for failure, but human-driven experiences are generally more forgiving than self-serve experiences. 
•  The upsell/cross-sell motion. Similar to the buyer journey, driving expansion among self-serve customers looks very different than doing so with enterprise customers. In the former you need to use the channels available to you (in product, email, etc.) and ideally surface these prompts at precisely timed moments in the customer journey. Pricing & packaging can also be a powerful lever here. For enterprise customers, upsell and cross-sell happens via the Customer Success team (or sometimes specialized sales teams focusing on the existing customer base), so you need to give them the resources — assets, training, etc. — to effectively have those conversations. 

The potential differences: 

•  The positioning, messaging, and proof points. Enterprise customers are trying to solve different problems — or at least at different scale — than smaller customers. That means your positioning and messaging, the language you use, the customer proof points, the use cases, and sometimes even the features you emphasize should be different across the two audiences. For each audience, you want prospects to have the same takeaway — "this product was made for companies like mine / people like me." 
•  The product & success needs. Enterprise customers tend to have more complex product requirements than smaller customers, and almost always have more rigorous support needs. This has implications on the product roadmap, your pricing & packaging, and your Customer Success model/staffing. 

Great question - this is very common in today's PMM landscape. There are 3 main product marketing differences:

1. Target audience
2. Messaging 
3. Value prop

For self-serve products, the target is usually focused on the individual user. Therefore, the messaging and value prop is focused on simplicity and solving their immediate problem, which in return helps them do their job better or faster. 

However, when selling to enterprises, the target audience is usually the buyer. Keep in mind - the buyer often times is NOT using the product every day. Therefore, the messaging and value props are focused on the future-state of the business and results in more revenue or saving time/money. 

I talked about this in detail at Product Marketing World in Chicago - you can watch the video from my talk here: https://youtu.be/Mbd0pUO1HXs