My company wants to go upmarket and increase the average sale price of its products. How do we do this?

Going upmarket is a company-wide initiative that goes well beyond just pricing. Your product needs to be optimized to support the next tier of buyers (for example more scale, APIs, supported languages, admin capabilities etc.). Your GTM engine needs to be recalibrated for selling up-market - from creating demand to qualifying pipeline and navigating enterprise deals for close. Your support and customer success playbooks must also be upgraded and developed for the new buying segment with more white-glove services, maturity, and value-creation models. You get the point, pivoting to go upmarket is a big deal for any company. Now as for pricing, are you looking at land and expand models - start with one business unit and grow into others, are you selling upmarket via channel partners or direct, are you selling a different product with a higher price tag or same product but more seats, APIs calls, data volume of whatever your monetization unit is? The answers to these questions should guide you if you need to completely change your pricing, or create an enterprise tier within your existing model.

1. Going upmarket is hard, but important to do. I think increasing your price and tackling a new customer segment should always start by looking through the product lens. The biggest first thing is to define the overall value your product brings (or would bring) to a larger customer base. While a company will have an overall messaging framework, messaging to a larger audience usually requires a different approach and often a tweak in how you message your overall value. Once you do that, you can take a look at your current product offering and see which features already fit the profile and needs you’ve mapped out. This can also guide your future roadmap and think through things you need to add to make sure your product solves the needs of these larger customers. Often, these features are around organization-wide control and governance as well as certifications like FINRA or SOC-II compliance.
2. Once that’s done, you’re ready to start tactically planning. You can decide if you want to make a new SKU for your pricing plan (probably an “enterprise” plan) that houses the features you already have available to just those customers or keep your current pricing and just start going after larger customers in your GTM efforts. You can then decide how you want to increase your prices. I’d recommend competitive research, some customer/potential customer surveys to generate insights, and financial modeling to understand how the new pricing will set your company up to hit their financial goals for the year and if you’re a sales-led growth company, test run with a few sellers and sales leadership. Then you’re good to start tactical execution!

Taking an existing product into a new market should always include pricing and packaging research. First, I would begin with some of the research methods that I've mentioned before. These would include competitor websites, review websites, marketplaces, industry analysts, independent research/survey firms, your existing customers or prospects, your existing partners, and your sales team, to name a few. 

Ideally you've been able to win some deals with the upmarket/enterprise customers you are trying to attract as you make your shift. You should definitely interview those customers and understand what features they find most valuable, what competitors they evaluated that might not be part of your current set, what things they wish were in the product but are not yet (you may need to price yourself lower until you can add those features in), and, if they will tell you, what they would be willing to pay if they were buying from you all over again. 

You may want to leave your current pricing alone for the time being and create a new package for the upmarket customer base until you get more of them. Ideally this new package or edition would identify features that would be applicable to that upmarket segment that were not necessarily appliable or as needed by your current segment so that you could justify the higher price. But even if you don't have different feature sets, you can still set higher prices for different segments by using other factors like revenue/employee counts to segment companies into the upmarket edition. 

Either way, make sure you are monitoring both segments with timely reporting and data so you make sure you are not affecting your current segment.