Great question and not an easy one. There’s a difference between saying, “let’s shift messaging to go upmarket but retain and continue to build for our core SMB base” versus “let’s shift messaging and resources to go all in on upmarket, even if that means neglecting SMB.”
If it’s the former, it’s much easier to do because you can shift all your prospect messaging upmarket but continue to engage and speak to your SMB base as you have been. And you’ll still have a product ladder or offerings that meet the needs of your SMB and so you can effectively segment and tailor messaging. For example, SMB ads can go to SMB landing experiences and upmarket targets can have their own messaging funnel. If that level of segmentation isn’t possible, and you can only advertise to upmarket, having a visible escape hatch or way to identify SMB is crucial so you can carve those folks off to their own tailored messaging area, even if that is secondary or on a separate page.
I’d also focus on ensuring your 100% aligned internally with regards to the conversion expectations of your tailored messaging. If you go fully upmarket in your messaging, are internal stakeholders comfortable losing your SMB conversions? Or is there a threshold you need to maintain in which case you’d want to test your upmarket messaging with SMBs to ensure it’s not too alienating.