How do you separate out your competitive positioning for two different plans of your product, while keeping a unified view, if the plans serve different customer segments?

Pricing and CI are two separate side of the same coin. Easiest way to win more business is to reduce your price. But that has consequences for revenue. Ultimately one product with different price points is aimed at a different cohort where price sensitivity, functional preferences and quality expectations get re-established. Let me keep with my electric car analogy from another question. Chassis and battery are a given as stakeholder. If now lets say you offer a service whereas you can change your car color up to 5 times a year. That appeals to a different type of a buyer. More in tune with fast fashion. To appeal to them you need to position the car not as an electric car but more the only fast fashion electric car. And price it in such a way that your costs are recuperated. Companies use this extension to address new segments once the core segment is saturated and growth needs to come from elsewhere

For Shopify/Shopify Plus type scenarios (also seen in Klaviyo/Klaviyo One, or Dropbox/Dropbox Enterprise), you end up creating two sub-brands. These names aren’t just different product plans - they are sub-brands with their own unique look and feel and web presence allowing for a separate space to provide your positioning. e.g. Shopify.com no longer has to take the burden of convincing the market that it is an enterprise grade solution - they have Shopifyplus.com for that. This extends to sales/CS conversations, analyst comparisons, case studies and more. At Klaviyo, we built two completely different pitch decks for Klaviyo and Klaviyo One - different colors, storytelling style, tone and voice, depth of content and product narrative

The more challenging, and common, scenarios is when you are serving two segments via two plans but can’t just create a separate brand. The answer lies in creative a master platform/company positioning, as well as positioning for each of the segments. Then applying that on a case by case basis to the surface areas available to you. e.g. On pricing page , easy to display both plans and their related positioning - even calling out the segment name (Think Box for individuals, Box for Business). Similarly, your sales teams can build in the right questions in their discovery process allowing them to take a tailored pitch approach - even using different elevator pitches and pitch decks and demos depending on the segment they are talking to. Ads can be hyper-targetted to audiences too and ABM programs already allow for personalization of messaging by segment/audience type. Web UX and navigation structures allowing visitors to self-select their segment of choice

The biggest challenge is the website home page - one of the least personalized areas of your marketing. What segment should your website home page speak to ? You have to decide that based on your strategic priorities. You can make it hyper-focused on one segment or generally talk to everyone as a platform. You can tailor the messaging to speak to the segment you are winning in, or the segment you are marching towards. No right answer here. Really depends on your strategic priorities and the role your website plays in your growth funnel. 

This sounds like a classic case of product family positioning, where you would define a common positioning for what makes Shopify unique across both products. And then absolutely, you would do separate competitive positioning for each product edition based on the needs of the customers it serves and the competitive environment.