It depends on where these requests are coming from! I'm always cautious with competitor specific one pagers because it's so easy for these to get back to the competitor. I've personally seen slides our competitors have made about us and this is a) legally risky b) detrimental to any partnership you might have with your competitor c) super easy to debunk when you see it neatly written down! We do come up with "battlecards" for all our major competitors that Sales can use to quickly respond to some of the most common competitive objections with key talking points.
I'm more supportive on one pagers around specific topics/functionalities/industries that your product supports. These can be especially helpful in buying decsions with many diverse stakeholders, as they can be easily passed around while your buying committee works towards consensus.
One last note on this is make sure to prioritize what you're producing. Some considerations include:
The best way to get a handle on the success rate of your enablement program is to evaluate it both quantitatively and qualitatively. On the quant side, it's helpful to do some regular sales surveys around satisfaction, whether that's quarterly or after every launch. On a scale of 1-10, how confident do reps feel speaking about new features or going up against competitors? You should also pull metrics like competitive win rates to get a broader view of how sales is performing overall. Qualitatively, it's very important to build strong relationships with both Enablement and Sales teams to access more informal, just-in-time feedback.
It depends on how radically different your Enterprise solution actually is and how unfamiliar it will feel to Sales. Something else to consider, is this a new tier or a totally new product?
Often your Enterprise solution isn't radically different from your Standard product, especially at launch. Also, if your sales team has come into contact with enterprise customers they're probably already clamoring for the enterprise functionality. If this isn't the case though and let's say you've acquired or built a more standalone enterprise solution and are trying to train your SMB sales team on it, I'd start slow and then ramp up. Make sure the team really understands the enterprise pain points the new solution is meant to solve. What's the value proposition? Key selling points? Starting high level this way, you can ramp your team up slowly on all the details. With Enterrpise sales, your volume is probably fairly low especially in the beginning so you can have a Solutions Architect or even PMM help out with demos until the Sales team feels more comfortable.
I actually have a Competitive Intel PMM on my team who works on some of these materials. It can be helpful to use a CI tool if you have budget for this. At Klaviyo, we also have a Creative team that helps out with customer facing work but you can totally create this type of material on your own with access to Powerpoint. Just be careful with making claims against competitors in writing as there's always the risk they could respond with some legal action if you aren't totally buttoned up.
I'd watch some recorded sales rep calls to form my own opinion on what's going on. I'd also follow up with the rep to get their perspective on challenges. Once you've diagnosed the problem, there's a few steps you can take:
It sounds like you may be cannibalizing yourself with overlapping product offerings. If customers are happy to use your cheaper product, it means the value of your enterprise package isn't crystal clear. I'd go back to the value prop on this one, what does your enterprise package offer the customer that's worth the price? If you feel you have that figured out, then it's just a matter of illustrating that through messaging. Show some super specific examples of enterprise brands that have seen killer value from upgrading and you'll have a more convincing narrative.
Another option here is to not give Enterprise customers the option of having a lower priced package. Depending on your pricing model, you can usually justify charging larger customers more because they use more data/have more servicing needs/etc.
Demo scrips and pitch decks can be very difficult to land, especially if you're dealing with a generally successful sales org which may be less open to change. It's super important that you get alignment with Sales so they don't just look at your deliverables as just a "marketing" thing and ignore them. Some tips: