AMA: Dovetail Product Marketing Lead, Alissa Lydon on Sales Enablement

I think the pillars of a great sales enablement program are: 1. Regular touchpoints - sales enablement is a never-ending program. So you must create rituals to show how important the program is and to create the habit where the sales team expects to engage with enablement regularly. Build the habit early and often! 2. Meaningful content delivery - building and maintaining a content library sales can self-service to find what they need can be difficult. But if you take the time to create and continually feed that resource, enablement can exist outside of your Zoom meetings, and live and breathe throughout the organization. 3. Two-way feedback loops - enablement shouldn't be perceived as simply a service that product marketing provides to sales. Instead, you should be cultivating spaces where sales feel empowered to give feedback on how messaging and assets are performing in market. This two-way street is a win-win for everyone. Product marketing gets valuable feedback to iterate and create better materials, and sales get to leverage those improved assets to sell more effectively! 4. Trust - at the foundation of the first three pillars is trust. It takes time to build, but by doing the above consistently you can build a connection between product marketing and sales where both teams are contributing to each other's success.

If there's one thing you want to avoid when developing and launching a new sales enablement program, it's rigidity. Too often, I see product marketers who are used to doing things a certain way. They have a framework that has worked in a past life or a playbook that was successful at another company, and they simply want to apply the same process to a new context. Doing this leads to friction that can doom a sales enablement program before it's even started. Instead, I encourage product marketers to bring curiosity into their planning process. Instead of just executing the playbook, take the time to understand what has been done in the past. What are the current ways of working, and why do they exist? If there were previous sales enablement efforts, why were they unsuccessful? What are the unique needs of the sales team? So often we get into the mindset that we have to act and deliver value quickly, but taking the time to truly understand the broader context you're in will give you valuable direction, and more importantly begin building trust with the teams you need to collaborate with to ensure the success of your enablement program.

Let them do the talking! The longer you present slides, the more likely they are to tune out and not engage. There are a couple of different ways I like doing this: 1. Find a champion within the sales org to help present new information and build credibility. For example, if you want to train the team on a new pitch, recruit a rep with lots of influence who can do some early tests in market, and then have them deliver the pitch and share their learnings in the enablement session. This is a win on so many levels. You battle-test the asset to improve it before a larger rollout, you get direct feedback on how well it works for the sales team, and you get a trusted voice advocating for the asset once it's time to launch! 2. Create spaces where enablement becomes interactive. This can include open forum discussions, small group activities, or even something as simple as pop quiz-style polls. Break up the monotony of slides, and find ways to bring participants into your sessions. It will be more fun, and increase the chance that your content will be absorbed.

I've found that the best way to get sales excited about giving feedback on how messaging is resonating is two-fold: 1. Make it an ongoing ritual. Set aside regular time that is devoted purely to feedback. Don't wait for sales to take the initiative, and set the expectation that they should prepare feedback for product marketing regularly. Set an agenda beforehand and give them the structure to ease the burden of preparing feedback. If you make things too open-ended, then you won't get the insights you are looking for. 2. Showcase how their feedback is having a positive impact on your efforts. For example, say that you're hearing from sales that it's hard to quantify ROI during prospect discussions. In response to that feedback, you might create an ROI calculator asset. As part of the internal launch, be sure to call out that this was a product of feedback directly from the field. The team feels good because they feel that their voices are heard, and because they have an asset that directly helps them.

This depends on the needs of the sales team that I am working with. But no matter the type of content, what makes it useful for sales is how it can fit into their preferred ways of working. For example, let's say that you want to train the team on updated messaging. You probably have an in-depth messaging guide that tells the broad narrative of your product (problem, solution, and value). You might think that you can just train the sales team on this new story, and leave behind the doc as reference material. What is more impactful is if you can take the content of that messaging doc, and present it in a way that works for sales. So instead you might create a "pitch guide" that helps sales understand how to map personas to use cases, organizes pain points accordingly, and gives guidance on not just the value of your solution but more specifically what features to show in a demo, or what questions to ask in discovery to evaluate that pain. The more you can tailor content to the experiences the sales team is having in the field, the more valuable your reps will find it.

The first thing to remember in situations like this is to lead with empathy. Sales is the toughest job in the business. It takes a lot of guts to be on the front lines of go-to-market - cold calling people who don't want to talk to them, pitching solutions to teams that are inherently skeptical, and constantly having to chase the number that determines whether or not they get paid. Just like everyone in the organization, they have a lot on their plate, and it's hard to keep a lot of things in your head. That being said, I also know how frustrating it can be when a salesperson can't seem to remember where you've hosted materials. I try to break this pattern by doing a couple of things: * Make sure I meet them where they are, and I mean EVERYWHERE. You might host all of your materials in Google Drive, but in my experience sales aren't spending their time looking through folders to try and find what they're looking for. Instead, I might take my most utilized assets and put a link directly to them as bookmarks in visible Slack channels. Perhaps I use a tool like Crayon for battlecards, but salespeople aren't logging into yet another tool to find what they're looking for. That's where I would leverage a Salesforce integration to surface that information directly in their workspace. It increases the odds that they will find what they are looking for. * Find champions within the sales team who can help nurture good patterns. Find ways to elevate that salesperson who knows where to find assets within the team, and have them show other members best practices. This can be done during dedicated enablement sessions, or more ad hoc. If a salesperson is asking in Slack where to find materials, ask that champion to answer the question, and walk them through the process of finding it. It's a great way to crowdsource coaching, and I've found that having it come from a team member has even more impact.

This is a real challenge, and I am curious to hear how other PMMs do this! My suggestion would be to take the onus off of sales in manually tracking how often they are using assets and how effective they are, and instead find ways to proactively get that feedback. One thing that I have done in the past is survey the sales team on which assets they use most frequently. It was a basic Google form that had them rate various assets in our content library (pitch deck, ROI calculator, product one-pagers, etc.). It isn't an exact science, but it does reveal sentiment within the team of which content pieces are the most valuable to them. Additionally, you can try to establish which materials are effective in closing business by doing some deal reviews with reps. You might look at a cohort of sales opportunities, and ask reps which content pieces they used during the sales process, and create a kind of content journey map. Again, it's quite manual, but even on a small scale, you can start to identify trends and understand how and where your materials are being deployed so you can continually improve.

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 first thing I would do is take the time to deeply understand what the biggest gaps are for the sales team, and what their immediate needs are. Enablement is such a broad program, and the last thing I want to do is waste cycles building things that the team won't find useful. Where are the quick wins that can jumpstart my enablement efforts? The second thing I would do is make sales enablement a reliable ritual with the team. Set time aside to be in direct contact with the team regularly (perhaps once every two weeks, or even once a month). Own the agenda for those meetings, and use them for whatever purposes are most impactful. You can provide product launch updates, do deep dives on competitors, hold open forum feedback sessions, and more. The benefit is two-fold: 1) It's a forcing function to start developing and delivering those needs you identified in step one, and 2) It is the foundation of trust with sales that is crucial to the success of product marketing at any company. If the team can rely on hearing from product marketing at a regular cadence, and you are delivering assets that create value, then they are more likely to give you feedback on how your messaging/positioning is resonating in the market, which sets you up for ongoing growth across all areas of the function.