How do you plan out what sales enablement content you'll make in any one quarter? How much of this is driven by sales versus product marketing?

It should be collaborative and I would somewhat divide and conquer by you setting up the enablement you know will be needed based on your PMM roadmap such as product launches and other new collateral (comp intel, pitch decks, research reports, etc…), and by sales leaders coming to the table with where they see their teams needing more help. Maybe it’s in deals around a certain use case, for a certain industry, or against a certain competitor. All this should be clear from the sales op data you have and allow you to build a program around it to support it.

In my experience it’s a healthy mix. A few key factors (not exhaustive) can should influence the type (and volume) of sales enablement content you deliver in a quarter:

• Stage of product lifecycle: How mature is the product and where is it in its lifecycle? This usually will dictate the volume and fidelity of the content you produce. For example, for early stage products, it’s best to keep sales enablement content light as you’re still in the process of assessing early customer feedback
• Sales feedback: Discuss what tools and assets will be most beneficial to facilitating customer conversations (especially if sales has had a chance to engage prospects / leads already). Are there priority sticking points that need to be resolved (e.g., why your solution vs. competitor X, etc.)
• Resourcing: Let’s face it - budgets and hours in the day are not unlimited. Be realistic about what type of content capacity you have at your disposal. Based on these constraints, prioritize around the assets that will drive the greatest impact.

I’d say it’s 50/50. Sales will always have lots of ideas and requests :) On the other side, I don’t want to spend my time creating content that Sales won’t use. It’s a good practice to understand WHY Sales is requesting certain content. Sales might request a detailed feature-by-feature competitive matrix, when you have your key competitive differentiators on a LP/webpage that’s easier to share with prospects. Then, it’s good to have an agreed calendar (w/ the Sales leads) of what you’ll produce that quarter, with some degree of flexibility.

Sales enablement content planning is a constant push and pull of what's coming from the inside-out (e.g. product launches) versus what's coming from outside-in (e.g. competitor updates). You must address both in your roadmap.

Focusing too much on the inside-out will create tension with the sales team as they feel like their needs aren't being met. The risk is that they stop engaging with your content, and no longer give you the valuable feedback your team needs to improve. Focusing too much on the outside-in creates a power imbalance where sales are dictating the enablement strategy, and product marketing simply becomes order-takers for sellers. That is not the position you want to be in.

Just as product managers must negotiate their roadmaps with key stakeholders, so must product marketing negotiate with sales (and other GTM teams) on their plans for sales enablement. Make it an open process, create a data-backed approach to help prioritize various needs across the team, and show the tradeoffs that are being made when deprioritizing certain asks. This ensures that everyone understands your roadmap, and is more likely to engage with your outputs.

The best practice for good enablement calendar planning is to understand what the business needs from a GTM perspective -and this alignment needs to happen at an executive and functional leadership level, between product ,marketing, sales and ofcourse product marketing. It is dangerous for either sales, or product marketing to be dominating the conversation

Now that is an ideal state. In reality, I often see the following models of enablement planning (Goal is to strive towards the ideal state)

1. The committee model - Typically in larger companies, there is a central enablement team that runs an enablement council or committee to guide on enablement calendar. They work with both product marketing and sales, to build an enablement calendar in advance - covering onboarding, refreshers, new products, new plays etc. Inputs could come from any source - sales may demand something urgent, or PM/PMM may want to push something urgent

2. The "Just-in-time" model - Typically in smaller companies, all enablement is often 'Just-in-time" being pushed by the executive team, or functional leaders, depending on the initiative. Nothing wrong in this approach - that's how startups remain agile as long as you are comfortable with context switching

3. The "Build the plane as we fly it " model - This is often when you are asked to fly with a half-built plane. e.g. a new product is launched with just a web page. And everything else - its pitch decks, special demo, call scripts, competitive comparisons, videos, etc. come later. Since you can't build everything at once, you end up picking the most important artefacts, or training needs, every quarter - and then go down the list. This model is also true when you are doing a complete messaging overhaul or major pivots

In all cases, I find that the natural rhythm of the business influences the enablement roadmap for the year, broken by the the quarter. For example, at a company I was in where sales cycles were 6 to 9 months long, Q1 and Q2 ended up being about new sales plays and new campaigns focused on pipeline creation. Ergo, enablement was centered around that (e.g. new value prop, new approach to discovery, new demos etc.). Q3 and Q4 were often about helping close existing pipeline, or 'firedrill' campaigns to fill any pipeline gaps and the content favors that (e.g. objection handling, competitive battlecards, pricing and packaging changes etc.). Product launches create their own enablement needs anytime of the year. Massive enablement happens around user conferences (Spring/Fall) or around SKO/FKO as they are the right forums to land the message

As Ryan said it has to be a collaborative effort. We have created a matrix where sales stages, marketing stages and product marketing stages are overlapped, and then map the content accordingly. This is how we identify which content piece needs to be developed. This is how we also check if the content is working or not.