How do you decide between focusing on SMB vs. Enterprise when doing messaging where you can only have one?

That's a tough call. What we've found recently is that as we've adapted our messaging for an enterprise audience, it's resonated less with small businesses. Some companies choose to vary their messaging by audience size (e.g. Shopify) others have one-size-fits-all messaging regardless of size. I think another option is somewhere in between where there are different reasons to believe, proofs and sometimes even value propositions depending on the size of the prospect or customer (but with other aspects of the messaging ladder remaining the same). I think it's difficult for messaging to work for all size audiences though so if the differences are extreme, it's probably wise to force a strategic decision about what audience to focus on before trying to write messaging to work for everyone.

If you can only have one I would defer to the priorities of the business. Are you investing more in enterprise initiatives or SMB? If that prioritization is unclear, I'd use market indicators, opportunity expectations, and recent successes to break the tie. 

You can also take a lower-lift approach to addressing the nuance of both. It is likely that your business operates similarly for both targets, provides similiar benefits for your top level business messaging. Then it could be as simple as an additional row of adjusted messaging to target each audience's key pain points and supporting proof points within the same messaging documentation. Then you can cater to the audiences more directly in your activation of the messaging in the market.

This question suggests PMF or an offering that can solve the (or some of the) challenges both segments face. If that's the case, read on. 

If that's not the case – stop – do not pass go, and do not collect $200. 

Every business wants to be seen as enterprise-grade/ready/insert-your-word-here. That's why early-stage companies often focus heavily on landing big logos with low margins; it's no more complicated than saying: "If Company X trusts us, you should, too". For my money, I'd focus on landing messaging that resonates with enterprise customers since those are often more complicated buying processes, more complex problems, and larger contracts. 

Your best bet, though, to show partnership with stakeholders is to identify the largest addressable segment (using your knowledge of customer pains, opportunities, and the competitive landscape), conduct basic TAM research, and make a recommendation. With that buy-in, you can be confident that you're making a decision that meets the needs of the business. 

Generally, this comes down to your company priorities. It is hard to do both well so here are a few questions you can ask to determine which approach is correct:

• What percentage of your new revenue comes from SMB vs Enterprise? How are your sellers organized SMB vs. Enterprise?

• What customer stories are more compelling to you target audience?

• Where are your competitors focused and where is there whitespace?

• Which target will help you get to your revenue goals faster?

To make this decision, I would bring the answers to the above questions along with a recommendation to your key stakeholders.