We have traditionally been focused on SMB / Mid-Market and are now trying to go to market to the Enterprise. What questions do you recommend we ask internally to get to product market fit with our new Enterprise pricing and packaging?

1. There are so many questions you could ask but I’ll give you a few:
1. Why do we want to go enterprise? How does landing with the enterprise land in our stack ranked priorities? Ask these to figure out how conviced your company is about going into the enterprise. You want to figure out if moving up-market is a mandatory priority versus something they’re interested in exploring since that will impact how you do this.
2. Do we believe that our product solves a clear need for Enterprise customers? Do we have features that are already meeting those needs and enterprises already finding some success with our product? What gaps do we have in our product and how will those be prioritized on the roadmap?
3. What are we willing to give up to win in the Enterprise? Would we be willing to miss our SMB targets in order to make this happen? This helps you understand how to load balance across the portfolio.

As mentioned before, taking an existing product into a new market should always include pricing and packaging research. Research methods include competitor websites, review websites, marketplaces, industry analysts, independent research/survey firms, your existing customers or prospects, your existing partners, and your sales team, etc.

If you've been able to win some deals with the enterprise customers you are shifting to, you should definitely interview those customers. Some questions to ask include:

• What current features do they find most valuable?
• What competitors did they evaluate that might not be part of your current set?
• What features do they wish were in the product but are not yet? You may need to price yourself lower until you can add those features in.
• What would they be willing to pay if they were buying from you all over again?

Internally, you should talk to the reps who sold those deals or who have sold to enterprise in the past and get their feedback on the same questions that you ask the customers. Maybe they can also identify some lost deals who would be willing to talk to you as well. You should also talk to your Customer Experience team to make sure they can accommodate supporting the new enterprise segment. You may need to create more white glove support or implementation packages. You may need to start working with implementation partners rather than doing post-sales activities in house. That could also affect your pricing and packaging as you move to enterprise.

Lastly, you should be sure to ask product, engineering and finance if you need to make any adjustments to the underlying product architecture to support those enterprise customers who are more likely to have bigger data needs, bigger compute power needs, more users etc. Ensure that your current cost structure will work if the product architecture has to change. Those costs will likely affect the pricing and packaging you use for your new enterprise segment.

Enterprises and SMBs have interesting trade offs of flexibility, utility and price. 

• SMBs may have valued an instant deployment self service solution, that accomplished most of their tasks but not bothered too much 24x7 support and/or security. 
• Enterprises are more likely to value customer success relationships, deployments done right (vs fast), the right compliance criteria and other customers like them (enterprises don't like risk). 

What does that mean for your pricing and packaging? 

• Are your support and customer success packages going to help them feel secure?
• Does your sales process set clear criteria for implementations, timelines and their success metrics? Does the SOW list out the feature lists correctly?
• Are you sure you are not nickle and diming enterprises? They'd likely rather get the right contract than keep re-negotiating with you.
• Have you considered bundling something like an academy/university/certification? Remember, enterprises don't like risk.
• Are you assuaging their concerns about needing a custom integration here or there? Or are you going to say a hard no? Having a custom build line item could solve this problem. 
• As far as pricing is concerened, are you sure you are pricing high enough? (Coming up from SMB, I would actually err to the side of high prices vs setting a low price bar that becomes harder to raise later)