AMA: Shopify Director, Revenue Marketing, Kevin MacGillivray on Sales Enablement

Here are a few winning strategies to keep sales on message including: * Sales often crafts their own variation of a product message to fill in gaps when the official version falls short or is incomplete. Ensuring that you've got clear, strong messaging that is up to date and readily accessible for reps to see helps prevent this from happening. * Prioritize the single most critical message(s) and make sure reps are hammering it home. * Learn from rep behaviour and adapt accordingly. Reps going off message can help identify hot spots that need better enablement, messaging, positioning, or even updates to the product itself. Harness this feedback loop. * Make the official version the most attractive version to use by backing it up with strong product claims, 3P validation, case studies, and data driven insights. Make it the path of least resistance.

This one is always a challenge, especially in organizations with a large product suite. Here are a few tips. * Create and prioritize updating a single source of truth that sales, CS, and support can access to understand what is launching, when it's launching, and where they can go to learn more. * Give as much notice about new features as you can. Even if all the details aren't finalized, get upcoming product releases documented in the calendar so supporting teams know what is coming (and the volume of new stuff). * Loop craft leadership in on a quarterly/monthly basis so they are aware at a high level what is coming down the pipe and can resource plan accordingly. * Know who your go-to's or single points of contact are for each supporting craft that will help you execute, troubleshoot, and work through any friction that may arise. Prioritize these relationships. * When there is a large volume of content in each release, you need to be able to pull out what is most important for sales and distill it down to bite sized messaging.

Generally speaking, I start with a relatively uniform bill of materials for each product to make sure we've got the basics covered in a consistent format. This includes things like pitch decks, one pagers, demo videos, claims etc. We leverage content management tools (i.e. Seismic) to monitor how/how often sales assets are used and adjust what we build based on efficacy and usage. We always listen to what our sales teams are asking for on top of this and build out a backlog, prioritizing what is requested the most. For example, we've been working on several ROI calculator tools recently that have been at the top of the sales team wish list. When choosing what to build we lean into assets that will help the most reps or help close some of our most valuable deals.

It can be challenging to enable a sales team that covers multiple verticals or multiple products. A few things that help here: * Limit the P0 priorities for the sales team to 1-2 major programs each quarter. Pick the top couple of programs, incentives, marketing campaigns, hero content etc. and lean heavily into these areas to drive focus. You don't need to ignore the other verticals/products, but this really helps focus training and enablement efforts. * Build modular content and enablement material that can be 70-80% vertical agnostic with slides/stats/case studies etc. that can be slotted in depending on the prospect. This builds rep confidence in the main talk track, but also allows for a flexible conversation. * Prioritize content for the biggest or most important verticals first and build out from there. It's ok for enablement and bill of materials to be iterative and get more vertical specific over time.

I'm going to go a layer deeper on this answer (vs. traditional stuff like pitch decks, one pagers etc. --> which of course are all very important must have). Here we go: * A set of data driven claims that show what has been possible in aggregate for existing customers/users of the product in question. * A library of case studies that demonstrate HOW existing customers/users were able to achieve positive outcomes (like the ones illustrated in the claims above) by using the product in question. * An ROI calculator tool of sorts that leverages a prospects own data inputs and business parameters that gives them a real time sense of what they could achieve with the product in question. Combined these three things help a merchant see themselves in the numbers and paint a picture of what is possible!

Who am I speaking with? How often? I have a regular connect with the Sales Director for audiences my team is accountable for where we speak about high level performance to strategy, gaps to target, escalations, themes we need to address etc. I also have a regular group connect with a collection of cross-functional revenue leaders for a more holistic conversation - sales leadership, enablement, merchant success, finance etc. These conversations happen on a bi-weekly basis and act as a mini-governing body for segment success. Regular communication and a strong relationship with sales is VERY important - true across my entire career. This is how you jump on opportunities sooner, fix problems faster, and level up the HOW on a regular drumbeat. What are sales teams looking for? Sales teams are looking for: a view of what product is shipping, marketing campaign calendar, campaign performance, TLDR on what is influencing inbound volume, updates on enablement and training, and a place where they can voice wins/concerns. How do we keep things productive? We keep a clear agenda of the things we want to cover. We make sure we get extra time to do deep dives if we need to on specific topics. We ensure the right folks are in the room to have a productive conversation. We try and base our discussions on data/real world examples. We set expectations up front on what we are able to deliver and by when.

Here are four great ways to measure effectiveness: * In the data --> what hard data can we look at (through Seismic, Salesforce etc.) that identifies how often enablement is used or how often it is leveraged when closing deals. * Talking to reps --> talking directly to reps and asking them what they are using and what is the most helpful is a great way to get a pulse on enablement efficacy. Especially if you've got a trusted group of seasoned reps you can check in on on a regular basis. * Listening to calls --> you can get into calls directly to learn how and how often enablement is used (and whether it is being used correctly and/or effectively. * Are we winning deals --> are we effectively winning the deals that leverage enablement materials? In other words does the enablement actually work and help reps close. If not, we may need to revisit.

One great way to do this is to build an annual/quarterly/monthly plan on what you plan to deliver and get buy-in from sales leadership upfront on the deliverables. If you've got this alignment upfront, it becomes much easier to avoid side quests to support specific asks on an ad hoc basis. Engaging with reps during the planning cycle for feedback and input will also give them a voice early on in the process and build longer term followership for the plan.

Here are what I think are the top (3) things to keep in mind with enablement for a global product: * You will always have to prioritize based on the regions with the largest TAM and biggest opportunity for impact. You don't have to create everything all at once. Select the most critical regions and create a backlog for enablement to follow in smaller markets. * Wherever possible, create modular content where you can leverage 70-80% of the material at a global level and create modular slides (of whatever the format) for content that needs to be localized. This lowers the lift for regional versions. * Understand upfront where you need to translate vs. where you need to fully localize. Full localization is usually more effective, but is a bigger lift. Have clear processes outlined for both that you can plug into in each instance to speed things up.