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Transitioning The Role Of Sales Enablement From Tactical To Strategic: 7 Practical Tips

Updated: Dec 28, 2020


We’re in for a very long and challenging era of uncertainty. In hopes to overcome loss of productivity, Sales Leaders and trainers are redesigning their strategies around onboarding and ongoing training. What might have worked prior to COVID times, may not be enough today and will definitely not suffice tomorrow as new standards for delivery and consumption are being formed at both ends: Enablers and their target audiences. In times of continuous changes and elastic workplaces, our target audience defines its own boundaries and balance between work and family time. The traditional Waterfall & asynchronous approach (elearning and online resources) slows down learners from accomplishing their goals for two main reasons:

  1. Instead of selling, reps spend time consuming “HOW TO” tutorials due to be forgotten or replaced with a newer version later

  2. Time spent on LMS or Knowledge Portals is time being wasted outside of the Sales Ecosystem.

Either way, you end up nurturing loss of productivity. Thanks to COVID, the inevitable change has started to accelerate and today SMBs as well as huge corporations are acknowledging the need for a new learning strategy where Adoption plays a key role in overcoming engagement hiccups. What they also identified is that they needed to transition from the traditional Waterfall approach to an Agile & surgical approach where help is offered proactively when a need arises within the application or the digital ecosystem. Today, the role of Sales Enablement is crucial to the sales organization more than ever. A new strategy is required to allow reps as well as leaders, to work within the elastic digital workplace and cope with the rollercoaster of changes while trying to execute on their role effectively. What that means is working closer with leaders, becoming more data-driven and putting more effort into understanding why, where and what are the areas that we shine at, and what are the areas we may need to improve on. I enclose below a few best practices that I have developed in my recent roles. These best practices can really make a difference in the areas of onboarding new hires faster, identifying gaps more effectively, aligning both Sales and Marketing to what really buyers need to consume, assessing where real or potential risks may exist, surfacing hiccups throughout the sales cycle and consequently lay the Enablement foundations for scaling up the business. One important note worth mentioning before moving forward - similar to adapting to a new sales methodology (or any other strategic change), these best practices can only work when they are reinforced by Leadership. Revenue Intelligence Revenue Intelligence becomes the “Must-Have” component in every hyper-growth business’s tech stack, either as an overlay app leveraging existing data, a new approach to process extracted data or part of a BI stack attempting to predict risks and trends. Whatever your business has decided to partner with, Sales Enablement can really step in to complement the traditional CRM data extract. In a nutshell what I refer to is - we, the Sales Enablement team, can help leaders understand WHY someone or some teams perform better than others, WHY the sales cycle is not where we aim to be, WHY someone or some teams park too much at a certain stage and so on. By definition, Revenue Intelligence might fall under the BI responsibility. However, the BI team does not spend time training reps, onboarding them, introducing new playbooks and providing feedback on calls with prospects, the BI team does not spend time shadowing calls or actively participating as internal advisors. Being there and taking an active part in these processes allows us to find out why some reps shine where others lag behind, why some reps struggle to adapt to changes whereas others execute faster on new playbooks etc. Imagine you’re about to introduce a new pricing system. Three months in or six months in, you should be able to get an idea of how this new model works, what is the impact and where it is most felt from a vertical perspective, region, team and so on. What you cannot see is WHY some individuals or teams are not adapting well to this new system. Is it related to their negotiation skills? Is it because prospects push back more than usual? Is it because prospects push back on a specific message? Or, is it because reps struggle to understand it themselves? And as a result - do reps struggle to communicate it successfully with their prospects? Now, imagine being able to measure all of that automatically and proactively. This is truly a game changer which can make a huge difference to the enablement team as well as leaders. Another example I am happy to share is the way leads are distributed among the reps. Theoretically this mechanism should work successfully. In practice, there might be some scenarios where leads end up at a junior rep’s pipeline or someone who still lacks the skills to address a specific use case or space, and as a result your business fails to build a healthy pipeline which might have been converted more effectively if those leads would have ended up at top reps’ pipeline instead. This is where Sales Enablement can step in and help to identify those risky scenarios based on conversational data and engagement analysis. Coaching Tier 1 Managers and transitioning them to act as Multipliers Let’s start with a fun fact - 46% of B2B businesses are planning as we speak to increase enablement headcount over the next 12 months. The reason is - the Sales Ecosystem is transitioning into a virtual era of an elastic digital workplace, but yet - more demanding and more intense. The 2nd fun fact is quite obvious - every business wants to scale up and grow. Put these two facts together and you’ll reach the obvious conclusion where Sales Enablement has to be more agile with broader responsibilities and at the same time, it has to scale out as well. This is why coaching tier 1 managers is extremely vital to the business, so they would be able to enable their team members and hence - act as multipliers, allowing you to develop new tools to address new markets and to mitigate new competitors etc. Coaching tier 1 managers consists of three steps:

  1. Gaps - identify common gaps (common denominator) between teams and individual gaps of bottom team members.

  2. Content - develop Coach The Coach sessions to address common gaps. Equip the managers with tools and content to reach out and enable individuals.

  3. Infrastructure - do you have the right tools and technologies to help managers spend less time tracking performance and invest more time coaching?

Today I rely mainly on two platforms:

  1. WalkMe’s Digital Adoption Platform - to proactively reach out to target audience

  2. Gong.io - to identify gaps across teams & sales cycle, and automatically report to managers

Bridging the gap (Handoff) between Marketing and Sales. Seamless and effective handoff means whatever Marketing produces is consumed effectively by Sales when selling to existing markets or developing new businesses from the ground up. When these two functions are perfectly aligned, you have a winning and field proven GTM strategy that actually works. To guarantee effective handoff between Marketing and Sales, both parties must aim to be data-driven. This goes without saying of course, and we’re not here to talk about a replacement for whatever BI system or Market Intelligence tools are being used. We’re here to talk about a complementary approach to fill in some gaps which may occur because of lack of granularity, capacity or understanding of what really happens before, during and after a lead converts into an account. The best way to explain that is by sharing an example: Let’s assume that our total addressable market consists of X verticals / industries. For each vertical, Marketing produces a dedicated tool box, and triggers the million dollar question - What does successful engagement look like? Where, when and how do we measure success? The tech stack today offers immense options to choose from and this is where Sales Enablement can come in - we can either own or orchestrate the process of extracting and visualizing the data to the level that suits our needs - identifying gaps and feeding back insights to Marketing and Sales. Change Management We all hate changes, especially during crises. Changes slow us down and sometimes come with an overhead of extra labor and time which we all want to avoid by all means. Put yourself in a rep’s shoes; changes mean spending more time on learning instead of selling. Every minute you spend on watching a tutorial or catching up on a missed internal training, that’s a minute you’re not selling. This is a Lose-Lose situation nobody wants. Sales Enablement can help when changes are introduced into the Sales Org in the following areas:

  1. Measure adoption and engagement through conversational analysis and call shadowing. Evaluate how, where and when the investment in those changes generates revenue, or not. Cross-reference that with Sales KPI and build a plan to bridge the gaps.

  2. Maintain business continuity when reps are not familiar with new processes or content by offering surgical help inside their digital workplace.

Risk Assessment Imagine being in a leadership position. You have your first cup of tea in the morning while observing deals that are about to close within this quarter. Now imagine being able to identify which deals are in risk because of ineffective communication between your reps and prospects, or because of improper CRM housekeeping or poor mitigation skills (pushbacks were left untouched). Now, imagine taking this one step further - imagine how the Sales Enablement team orchestrates this process for the entire team and leaders by automatically surfacing those incidents and reporting to relevant stakeholders, and at the same time coaching reps how to successfully overcome it in the future. The biggest impact of the above is when you cross-reference behavioral hiccups (which introduce risks) with CRM data, blending them together can drive strategic decisions. For example - are there any handoff issues? Redundant actions? Are demos delivered too soon? Do reps deliver free consulting to non-DMs? Do sales demos sound too technical? (as Marcus Cauchi perfectly describes them - Features And Benefits) Reactive to Proactive Surprisingly, even today during COVID crisis, businesses and training teams are still relying mainly on self learning resources to help reps when they get stuck. This is actually frightening when you think about remote workers with less tolerance to errors working in a very demanding space and schedule (EOQ). What needs to happen is transitioning the entire business from reactive to proactive engagement.

Here’s my own personal experience - In the past I used to spend hours and weeks creating content and hoping that reps would pull the data and come back to me with feedback and questions. When I joined WalkMe, I decided to drink from our champagne and reach out to reps and teams through proactive & segmented content. Later, I could track engagement and act upon accordingly. Transitioning to Proactive Content Engagement saves a great deal of time for reps, managers and Sales Enablement. Replacing a one-size-fits-all collateral with a surgical help inside the application allows reps to skip the long and tedious journey to external resources and thus waste time on self learning and loss of productivity. Collaboration The bigger our organization is, the harder it is to avoid silos of information. When we come across important information while meeting with prospects, how can we help making sure this information reaches its final destination successfully and effectively? Usually, information is shared via emails and social media channels. But again, the bigger the organization is, the less effective this approach will be. On top of that, how do we align everyone to the latest updates and best practices around competition, pricing etc. ? How do we pull feedback from reps? How can we help save time when consuming important and frequent updates? Here is my own personal experience with Gong.io: By setting specific tags associated with teams and verticals, today reps can ping specific teams at specific times of need, and ask them to listen to snippets of calls instead of sending emails and waiting till they open it and take action. Moreover, leaders share positive feedback on Gong.io and thus give stage to success, allow others to replicate what works well and help to motivate their team members, gain confidence in their early steps of their onboarding journey or as they assume a new role within the organization.