AMA: Square Director of Content and Launch Readiness Enablement, Charles Gryor Derupe on Sales Enablement

It's essential to first understand the expectations of your sales leadership, common denominators between successful reps who achieve those expectations, and availability of data to your enablement program. Here are a couple of questions to ask before you get started in creating a measurement plan: * What types of habits do they need to be able to do their everyday work by Day 30-60-90 days? * What are the expectations of your leads? Compare this to enablement insights on what can reasonably be achieved based on historical benchmarks. * Which reps have the most successful ramp numbers? What's the common denominator between all of them? * How long is your onboarding program, including reinforcement training after boot camp? * Do YOU have the data and reports that can show comparative data between reps? A lot of these questions really focus on setting benchmarks on four factors which I've seen are generally performable by many teams: 1. Confidence levels (Subjective): What are your reps' confidence levels around knowing and selling your products increasing over your ramp period? Is there improvement over time? Are you asking this based on various categories such as product, sales skills, and tool usage? 2. Lead Assessment (Subjective): Have their leads fill out a scorecard with guided skill categories based on your sales methodology following your reporting cadence. Make sure that there is guidance on what each category means to minimize the need for calibration. 3. Tool usage (Subjective and Objective): Do your reps know how to use their tools? Do they know where they can access the supporting documentation and guidance after their onboarding program? Are they accessing these tools and using them in the first place? How do they measure up to usage benchmarks - focus on effectiveness later after ramp as I recommend that these should be measured after reinforcement training past onboarding/ramp. 4. Activity, Deal Velocity and Attainment Benchmarks (Objective): How many calls are they making? How many prospects are they sourcing and reaching out to? How many deals are at various stages by 30-60-90 days - are they building and moving deals through their pipeline? Are they achieving the benchmarks/objectives your team has set for win rate and ramp attainment numbers? Hopefully, these categories help to start somewhere. Curious to hear what other enablement leaders have used as well.

Thanks for the question! There are three ways that we go about this: Focus Groups, Open Requests, and Analytics. First, I'll mention that all content should point back to your team's goals and objectives. What are you trying to achieve as an organization and business? Who are your target audiences? Will you be focusing on your ICPs or perhaps reinforcing the weakest sales opportunity? Are there any spots in the buying journey that have gaps and need to be addressed? These will ensure the content and strategies are giving you a north star and some hypotheses for the tactics below: For focus groups, we typically do a quarterly check-in with leads and they will recommend a few folks who are passionate about content. This helps us to get a pulse on what their biggest pain points are and we then diagnose and prescribe content. Typically specific pieces here are more general, like requests for "case studies" - which require more digging. For open requests, this is a typical form that our reps can go in and request content throughout the quarter. We send out a blast to the team reminding them, which is typically paired with a survey. Lastly, for analytics, we take a look at some factors: * Content searches with no results (what they want but aren't available) * Content most used but with low engagement (to help us understand what needs to be edited or made more of) * Look for reps who are using your content the most and the least and go back to focus groups to interview them Hope these help!

This answer is purely based on opinion, so please keep this in mind. I believe that any new tactics and strategies need to be relevant to the sales methodology set by the enablement team. Why? Reps, especially those that are "green" to the field, need a repeatable, consistent skill development structure. Additionally, this methodology should be where onboarding, ongoing reinforcement training, and content should map to. Adding new sales tactics and strategies are most effective for experienced reps who have already mastered their own selling methods. This doesn't mean you shouldn't or can't share some cool articles or resources for these new tactics and strategies - especially cool non-enablement resources and tools they can use to implement those methodology-mapped skills. A good example of this is how to sell through social media, where selling skills like good discovery, creating interest, and driving the next steps, etc. can still be incorporated into this new selling channel. Sharing knowledge should be part of the Sales culture. However, enablement programming should prioritize established methodologies for consistency and to make your impact measurement as easy as possible. 

I very much understand how this is difficult, especially if you have a distributed workforce and if budget constraints don't give you the ability to get folks into one place. I'll share a common approach that my peers from across the industry use (since I focus mostly on content) that can help set this up for success: * When: Try trying these real-world experience workshops during times when you do have some sort of gathering. Perhaps that's SKO or a bi-annual regional meetup. Work with leads to ensure this is expected programming when they gather in a centralized office. * How: Identify how some key skills (whether this is discovery, negotiation, driving urgency) and teach on strategies and frameworks. Then identify some moments in non-work environments when we use these. For example, when you do discovery, can you challenge them to approach an acquaintance, or even stranger, and give them the 3x Question exercise? * Next Steps: Follow up with their reflections and experiences in another session or post-session reinforcement training. Whether that's a module they can add their experience to, or gather some of the real-life scenarios straight from them and do a follow-up async training that would challenge other team members to try that 3x questions. You can even roll these out with managers with facilitation guides and do some kind of improv exercise session for their teams. Really, at the end of the day, you need them to practice with a framework in a controlled environment, take it out in an uncontrolled environment, and reinforce in a controlled environment.

This requires a good amount of cross-functional work, especially with your sales leaders. If you have a forum where there are weekly, monthly, or quarterly business reviews, I would request adding sections with a clear format that guides front-line leads to give you can get key insights gathered from the leads on common trends. What were the pain points/key needs/objections/drive to the next steps? This is the most scalable way of finding these out. These will help you to understand the key skills that need to be supported. Next - tools, tools, tools. These are a bit more manual. I recommend using a call conversation recording tool, a mass outreach tool, and a content management system. For call conversation recording, you can ask managers to recommend one "good" call and a "bad" call for your team to listen into. This doesn't give you how to make improvements, but it does give you a direction to create a framework for benchmarks of success. For outreach and content tools, take a look at the most engaged content and cadences. In these cases, actions speak louder than words, and you can decipher what good framing and messaging look like to create a framework and benchmarks of success. This is much easier to facilitate if you have a QA team that can create a scoresheet and report on behavioral changes. However, many teams do not have this function yet, so I would start small and focus on 6-10 calls/emails. Reporting these can really jumpstart more support and cross-functional excitement and surface any research work from your product or marketing teams' research.

Big question, but I'm happy to share some small factors that can really help to align and at least surface areas that enablement professionals can miss: 1. Know when and by whom business reviews are created. Even if it's async, understanding the target numbers, target audiences, and key strategies can help you understand where there are areas of opportunity. If you don't have this (common for early business organizations), gather feedback, create a base document of your strategic focus areas, and then gather feedback from top leads. 2. Align yourself as an enablement individual to understand where in the sales selling journey these numbers/initiatives align. For example, maybe your organization wants to increase top-of-funnel conversion. You'll probably want to focus on outreach efforts like effective outbound emails, cold calling best practices, and effective value-selling content to use for outbound campaigns. 3. Be aware of any sales leads' initiatives that they may start without enablement knowledge. This is very common when in hyper-growth mode or when an enablement team is so strapped that they have to say "no" to projects. At least being aware will help you to consult and map out what they are doing. 4. Report on your findings and annual/quarterly strategies and key initiatives for feedback. You'll get comments on whether you're on the right track and can provide call-to-actions with your team on areas that they can support.

I think the easy answer here is "buy-in" from your leadership. But what does this actually mean? They can say it, but that doesn't always mean that they'll prioritize or even fund it for growth. The approach of top-down is 100% the way to go in my experience but here are a few tactics I and my peers have used to reinforce this: 1. Get DRI's from leadership to support key initiatives and ask from top-leads who they would recommend to be assigned to them (frame it as "career growth opportunities"). Collaboration on top projects means that they have a vested interest in seeing it succeed as they're also putting hours into them. I wouldn't depend on them for building the initiative content per se, but they can certainly give good feedback and support on comms and accountability. 2. Communication! Do you have the right, centralized channels where all enablement content is available? But, do you have these paired with something they need daily such as product launches or process updates? 3. Speaking of communication, share your results with leads and cross-functional partners. Proving effectiveness (both objective and subjective) creates the belief that it's worthwhile to invest in, even if it's just giving attention. This could include weekly updates of quarterly business reviews. 4. Make it fun! I know that budgets are somewhat strapped, but prizes for participation work well. I often hear competitions are also good, but unless it's tied to making them something that helps them close deals faster or get some kind of reward (like a spot in annual President's Club-type incentives), I usually find it ends in just fun.

Great question! There are three specific ways I do this: 1. There are some annual reports done for Sales Enablement that come from third-party sources like Forrester and Gartner. These may be gated, but sometimes they are sent by tools vendors. 2. Use your tool vendor resources! I always ask my CSMs for all the tools we own if they've created an annual trends report or a "best practice' doc for their specific tools whether it's outbound tools, content engagement, knowledge, etc. They have these for their own product/core marketing behind gated sites but since you're already a customer, they should be accessible to you without the barrier. 3. Forums - one I follow is the Sales Enablement Society forum where professionals ask questions. And, I guess we should give Sharebird a shoutout too!

I'll be honest, I've been in the Sales Enablement industry for a while and this is something that takes so much time to master and has so much nuance depending on your organization's structure. Here are some tactics I use that have helped me get 80+ people in my last annual strategy review. It boils down to these three things: 1. What you did: I LOVE quarterly business reviews. Now let's be honest, I HATE writing them, but they are very effective in getting engagement. The two questions you want to ask here are: 1) Who's the audience(s) I'm trying to activate? 2) What information are they looking for that would gauge proof of investment return and guidance? For me, I typically stick to a common format: * Divide the document by program * In each program, share objectives that you've set at the beginning of the quarter/year, what major projects were activated to address these, achievements, key insights and feedback, and next steps (how you're building on it, how you're pivoting away from it, and what you need help with by cross-functional department) * Tag specific people you know that would be interested in areas that pertain to them * Create a read-through event and ask folks to add comments and tag others who would be interested * Leave room for discussion of key themes at the end 2. What you're going to do: In addition to the quarterly business review, I do an annual review that considers any strategic plans for our key audiences, mostly this will be Sales Leadership's north stars. If you don't have these plans, go off of the business goals and vision for the year (team restructuring, market expansion, change in target audiences, etc). Here's my typical format: * Goals and objectives from the previous year and share loosely what your team achieved * Key insights that are going to guide you in the new year - changes in team habits, cross-functional partnerships, industry changes * Identifying those business objectives and the strategies (the direction, not the roads) you'll be taking to get address them - focus on why you are doing this from an enablement professional perspective * Divide the following sections by quarter, refer back to the objectives and strategies and key initiatives. Make sure to call out dependencies, financial/cross-functional resources needed, priority levels. This is a great place to be clear about who you need these from and ask for DRI's from their teams through comments * Give gratitude to your partners for making this happen and look forward to the collaboration needed to make this happen 3. How it's doing: These are weekly or monthly updates on those objectives and key initiatives. Share your current state in achieving those objectives and the deliverable progress for key initiatives. I also include some key themes and insights that we see in the data and feedback we hear from reps. This is also a great place to share what you're hearing from the industry/enablement world and how you plan to integrate them. All of these have really jumpstarted interest in our programs by being clear on guidance for why and how your partners can help will get it going. Make sure that you secure clear partners, project owners, and recurring times set to meet with them. Hope these help!