John Kinmonth

Love this question. This will differ at every org, but for me the gold standard is win/loss ratio and booked revenue associated with a sales play, along with qualitative/sentiment data on whether it's resonating with customers (pitch recordings, feedback from sales, etc). These are not always easy to gather (and the first two might be outside of your official PMM remit), but they will really point your enablement efforts toward ROI. Other traditional measurements are more internal adoption- or checkbox-focused (passing a certification, attending a training, downloading or using an asset), but it can be harder to glean whether your enablement efforts are effective from those measures.

Great question. As someone who's worked in a number of startups, I can definitely relate to the pain of trying to do too much at once. In terms of prioritizing your enablement development/rollout across sectors/personas, here's how I think about it: 1. ARR talks: Run the numbers on your serviceable addressable market. Basically, look at the sector population and your average deal size or customer lifetime value to stack rank the opportunity by potential $$. 2. Ability to deliver against customer pain: It's tempting to push forward based on aspirational use cases, but spend the time mapping your ARR opportunity to how customers are actually using the product. Prioritize the audiences that have the most straightforward path to value. 3. Once you have the potential $$$ and ability for your product to deliver, it becomes more of a straightforward discussion for enablement priorities with your sales leaders. Start with the most lucrative/obvious use case, roll it out to sales teams, and use the customer insights to improve the next sales play* you develop. *In terms of the enablement itself, I'm a big fan of modeling out expected ARR based on usage or firmographic data so that account executives can prioritize whether it's worth their time to run the play. In addition, less is more—keep it really simple to follow and provide just the critical information they need.

Tell Kevin to pay better attention! Seriously though, that's frustrating, but I'd make sure it's not just isolated to that one sales member (are there other reps that can't find artifacts, but just aren't saying anything?) A lot of times, if I'm having a specific issue with an account executive or solution engineer not getting what they need or giving lots of feedback, I'll recruit them into a braintrust working group so they can help serve as a champion or expert for the specific initiative. Maybe Kevin could turn into your biggest advocate for your next sales play.

Here are some of the problems I often see with sales playbooks: 1. Too much information/time demand up front – If you're asking reps for 5 hours of study time upfront, you're likely going to see poor adoption. Instead, provide guidance to help them size their opportunity based on data, and then provide just the critical next steps for them to move the opportunity forward. We need to be cognizant of sales teams' bandwidth and not flood them with info about every facet of the problem space. 2. No data-driven opportunity sizing. A rep should be able to use your guidance to figure out a general opportunity size based on their account's current usage or firmographic data. 3. Oversimplification of problem space or pitch – This is contrary to the first point, but if you're over-simplifying a pain point or trying to apply one-size-fits-all thinking in a talk track—you'll lose credibility with customers (and the reps who have to deliver the message). Provide clarity/proof on paths forward for complex problems, but be wary of pitches that overpromise on a really hard problem.

For me, the gold standard is whether an associated sales play is helping improve win/loss ratio, deal cycle times, and booked revenue, along with qualitative/sentiment data on whether it's resonating with customers (pitch recordings, feedback from sales, etc). For example, if we project a revenue opportunity of $XM associated with a specific sales play, what is the percentage of revenue we've actually booked? If it's falling short of projections, is it because sales isn't talking to the right person, the messaging/positioning isn't right, or we're missing a critical competitive feature? I don't see this approach as an easy button solution, but it can be a way for PMM to really shine in an organization. Other traditional measurements are more internal adoption- or checkbox-focused (passing a certification, attending a training, downloading or using an asset). While these should be gathered to understand whether sales teams are actually using what you're building, it's hard to glean whether the artifacts are actually effective.

This depends on the makeup of your org. If you have dedicated sales enablement, they'll typically orchestrate the program with sales/customer success/PMM/PM leadership, and PMMs will serve as SMEs. If you don't have a built-out sales enablement team, PMM should play a forward role in formulating the theme/sessions/objectives. Either way, it's a great forum for PMMs to connect to sales leaders and listen to their pain points.