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Top 5 Takeaways from the #DF19 Sales Enablement Soiree

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The biggest event for the sales enablement community in San Francisco, the Dreamforce ‘19 Sales Enablement Soiree, has come and gone but we’ve never been more excited about the future of the space. Here were our biggest takeaways: 

1.)  A strong sales enablement program aligns the top down sales strategy with actual day-to-day actions and has a clear charter for what sales enablement means for your org, cross functional partners, and company

In almost every session, some sort of joke was made about how the term “sales enablement” was not around when the speaker started in their role. As a relatively new function, the awareness, expectations and perception of sales enablement is constantly changing as the function evolves.

 As John Dougan (Global Director, Sales Enablement) from WorkDay stated during one of the sessions, “Sales Enablement, is and will continue to become more complex because the job of selling is getting harder.” Creating predictable growth and outcomes, increasing the productivity of your salesforce, and unifying your strategy across a global team has never been more crucial or difficult to achieve. 

So what are some ways that successful sales enablement teams are doing this today?

Chad Dyar (Director, Sales Enablement and Strategy) from Hearsay Systems said that his sales enablement team acts as the strategic partner that unifies all of the cross-functional teams. His team is the bridge for these separate orgs with different KPIs. For example, right now he is in the midst of moderating 2020 objective planning across departments and making sure that at a high-level, the strategies are aligned.

Another strategy is to bring cross-functional partners into the sales enablement journey as much as possible. When more teams are involved and bought in, this leads to  increased alignment, leadership buy-in and even increased budget. 

2.) Sales manager buy-in is critical to the success of your program

David Mattson (CEO) from Sandler Training said it best: “Sales enablement should really be called sales manager enablement.”  Sales leadership makes or breaks everything that sales enablement does. They need to champion, reinforce and hold teams accountable for what teams are deploying. If they don’t, it breaks down. 

Onboarding and equipping sales managers with the skills they need to effectively manage and share  information with their teams is crucial. As it stands today, many are not onboarded properly. A pattern we see time and time again is that an all-star individual contributor gets promoted to manage a team but does not have full managerial competencies, the experience to work effectively cross-functionally, and operational skills needed to be an effective leader. The hope is that they will learn these skills, but often they are not given the time or guidance to do so.

As John Dougan stated, “An AEs job is the hit their number. The manager’s job is to inspire and empower their team, which ultimately should result in them hitting their number.” A manager should be focused and evaluated on so much more than just their number. There should be a number of core competencies that align with a company’s objectives and culture that this manager should embody.

Investing in an exceptional onboarding and enablement program for managers, bringing them along throughout the sales enablement process, and continually getting feedback and their buy-in will create a cohesive program from the top down. 

3.) The secret weapon you should be leveraging better: sales collateral and your customer journey

Jen Spencer (VP, Sales and Marketing) from SmartBug Media kicked off a session with the question, “How many of you have some form of celebration when a sales deal closes?” Almost the entire crowd rose their hands. This was followed by, “How many of you have a celebration or a way to acknowledge the collateral that’s used to close the deal?” There were audible laughs and not one person raised their hand. 

Sometimes the thing that pushes a deal over the line or serves as the original hook with a prospect, is our sales collateral. But how do we track the influence of it effectively? Optimize our content strategy? Tailor it to each segment/persona?

Charles Derupe (Sales Tools and Content Manager) from Square stated that they enable their reps to have more effective conversations in terms of value and differentiation by tying the customer and sellers journey together. From a tactical perspective two examples are 1.) aligning marketing and sales pipeline metrics/activities and 2.) in-context content suggestions depending on the context of the conversation (industry, stage, etc.) 

It is important to understand the end-to-end experience and optimize it for your customers in order to reduce friction and drive quality engagement throughout the entire process. A customer-centric approach not only benefits customers but also the field and the rest of the organization. 

If you’re working closely enough with your customers, you should be learning from them, molding your strategy with them and bringing them along in the change management and launch process. 

4.) Create a customized outreach strategy, continue to iterate on it, and learn from the data

We heard sales enablement leaders talk about how their sales people lead with customer pain point discovery, persona-driven selling, industry-specific messaging, and trigger events for their messaging. While it  differed from company to company, what remained consistent was that every single company was trying to create a scalable, repeatable motion that was constantly evolving. 

There was also a common consensus that you had to tie your activities at a micro level to your strategy at a macro level. For example, if you are tracking cadences closely, you need to monitor the messaging or sales play used and then tie all of that back to revenue. Most people were using SFDC for data quality but many were also using other tools such as Gong.io which would aggregate trends. 

Something that works one day, may not work in the future. Being creative and data-driven seemed to be a unanimous strategy. Alex Kremer (Sales Manager) from Outreach shared that they embrace a culture of celebrating wins and losses so that you’re always moving your strategy forward and learning from mistakes. 

5.) Constantly evaluate what you are doing and change it often

We had the pleasure of hearing Paul DePodesta speak, the main character in Michael Lewis’ Moneyball: The Art of Winning an Unfair Game. Surprisingly, his approach to MLB was not that much different than the way we should be thinking about sales. A quote that stuck with our team was “We had a long habit of not thinking that anything was wrong. This gives it a superficial appearance of being right. If we weren’t already doing it this way – is this the way we would start?”

Just because something is not broken doesn’t mean it cannot be better. There are so many unconscious biases that affect our decision making every day. Even if you are building a company from scratch  so many things can affect the foundations: demographics of your employees, diversity of thought, tools you invest in, previous company cultures – the list goes on. 

When you are deciding how your sales team is going to operate, all of this unconsciously affects what you roll out. Being aware of these biases and then being open to change based on other perspectives and data is key. When you see something repeatedly showing up in data – your outreach volume isn’t high enough or your EMEA sales numbers are continually declining – you should truly take the chance to investigate and evaluate it. Look at the entire system, not just that small part of the equation and ask yourself. “If we weren’t already doing it this way – is this the way we would start?”