How to Tackle the 13 Major Challenges of

Sales Enablement

GUIDE

2IntroductionEvery job function has its own particular set of challenges. While the concept of a sales enablement role or department might be new, the challenges surrounding it are not. Now that many companies have begun focusing on making sales processes more efficient and effective, its easier to identify the top challenges of sales enablement.

Brian Groth is the Sales Enablement Manager at Xactly Corp, and has experienced numerous challenges and tribulations associated with sales enablement firsthand. Throughout his 18 years in sales support/enable-ment roles, Brian has seen how inefficiently sales organizationseven the sales team within his own companycan operate. As a result, he felt compelled to find a way to save Xactly the time and money wasted by being inefficient and disorganized. Brian identified the main challenges he observed, and asked himself:

How can marketing better support sales to provide relevant, timely and accessible content?

How can sales management put the right processes and tools in place for reps to sell effectively?

What are the best practices for training, onboarding and coaching to foster consistent learning in the sales organization?

What organizational structure and strategy will best prepare the sales organization for success?

Brian has become an expert on solving these problems for his own organization, and has shared his solutions with us in this guide. Brian introduces and explores the 13 major challenges of sales enablement, as well as the strategies and solutions that your own company can apply to its ev-er-changing and growing sales enablement function.

3Table of Contents

I. Marketing Support a. Content Creation b. Content Management c. Lead Management d. Role Guides

II. Managing the Sale a. Sales Process b. Sales Methodology c. Sales Tools

III. Sales Training a. Sales Kickoffs b. Onboarding c. Coaching

IV. The Bigger Picture a. Organizational Structure b. Sales Strategy c. Change Management

Conclusion

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41. Marketing SupportSales and marketing alignment is key for an effective and efficient sales function. If marketing and sales arent able to work alongside seamlessly, neither will operate efficiently and tension between the two will increase. Its important for marketing to develop the processes and create content nec-essary for sales to sell efficiently. This includes external collateral, internal training and onboarding documents, and lead generation and management.

Content Creation From a sales perspective, content creation is the process of writing, curating and sharing collateral that a sales rep needs for conversations with prospects. This content includes sales presentations, whitepapers, case studies, and reports. But it also includes the internal training and onboarding doc-uments a sales rep needs in order to understand his or her role.

Why is it a challenge? Creation of customer-ready materials usually bleeds between marketing, sales and sales enablement roles. Further, the creation of how-to internal documentation and guidance usually falls to a variety of teams. For example, IT might explain a how to access or utilize a tool, but someone in sales might explain how to best use the tool from their own perspective, and HR might own the training of a skill. With many different perspectives surrounding the creation and use of a single piece of content, it can be difficult to consolidate content and keep messaging consistent.

5What can you do about it? First off, its important to keep track of all content in some logical manner that makes sense to your team. You can create groups of content organized by sales presentations, product details, customer case studies, sales skills, managing pipeline and opportunities, working with partners, and so on. This process and organization strategy will undoubtedly be different for each company and team, but being able to search and consolidate content into specific groups will make life simpler.

Content Management In sales enablement, content management includes the processes, technologies and people who manage the content that a sales team needs. Content Management Systems (CMS) exist to help entire companies, or divisions of it, to publish, organize, update, manage, version, and eventually remove content.

Why is it a challenge? Sales reps need both internal documentation and customer-facing content. There are usually differ-ent authors for both of these, as we discussed in content creation. Multiple authors means that con-tent is more frequently lost or saved incorrectly, meaning sales reps spend much more time search-ing for or creating their own content. Ideally, sales reps only need to refer to one location to access whatever content they need. Further, this one system can provide the right content for that sales rep at the right time during the sales process. Managing the content while taking all variables into account to determine whats right requires the expertise of the sales process, sales roles, customer segmentation, product details, and much more. Many companies face a huge hurdle when attempt-ing to provide this content at the right time while reps are swimming in a sea of content from many different sources.

What can you do about it? The number one thing sales enablement individuals or teams can do to help with content man-agement is to educate both sales and marketing teams on how the other team operates. Because marketing teams are responsible for the majority of content creation, it is important that they under-stand how sales teams sell, what they focus on when selling, and what content is important to them at different stages in the selling process. Sales must also understand how marketing creates and updates content, and both teams should agree upon where the final versions of content live and what the process is for updating or changing them. One way sales enablement teams can take is to adopt a single and shared content management system. Ensure that sales and marketing are com-mitted to using the shared system and that the complexity is hidden from sales reps. By exposing only the right content at the right time during the sales cycle, marketing can be sure that messaging is consistent and content is relevant for the customer. This way, sales reps know exactly where to go for the most relevant and valuable content for the customer with whom they are trying to resonate.

6Lead Management Generating leads is often considered a marketing responsibility, but some companies are beginning to adopt a new role of Sales Development Rep (SDR), whose job is to verify marketing-generated leads and create new leads with the goal of scheduling quality meetings for sales reps. Lead man-agement is the set of systems and practices a company uses to generate new potential business. It is generally operated through a variety of marketing campaigns or programs, and requires collabora-tion between sales and marketing teams.

Why is it a challenge? First, a company must choose whether this will be more of a sales or marketing function, and then decide on the process in which leads will be managed. Once its decided whether the SDR roles report to marketing or sales, they have to become experts at social selling, cold calling and email-ing, delivering a value proposition, and any other strategy your company uses to qualify leads. Plus, there are many tools focused on prospecting, lead management, lead scoring, and email tracking that SDRs should be at least familiar with. Not only is it a daunting task to create this process and train SDRs, but it is an ongoing sales and marketing responsibility to maintain the integrity of the lead management method.

What can you do about it? Sales enablement teams can partner with marketing regarding lead scoring and distribution tools, as well as ensure that SDRs have the right email templates and talking scripts to reach out to leads. They can also constantly check that all of these are working with the companys CRM and email systems, and are the most effective and efficient tools for reps to use. Training the reps to prospect, nurture and manage leads needs to be an ongoing effort, since the SDR roles have high turnover (they often move on to full sales roles). Call scripts and email approaches are always being refined based on what works best, so this is an area of the sales organization that is fast moving and rapidly improving.

Role Guides When new sales reps are hired or get promoted to more senior roles, a role guide is the written document that explicitly outlines their primary goals, activities, tools and overall job objectives. Role guides should be planned by same-level employees, upper management and any other parties that work directly with the person holding the role being described.

7Why is it a challenge? Creating initial role guides for each role in a sales organization is a significant task, especially in or-ganizations with many levels and layers of employees. All companies organize employees differently. For example, if your sales organization segments reps by SMB and Enterprise accounts and has tiers per role, then it gets more complex and time consuming to create these role guides. As organiza-tions grow, grey areas within these roles increase, and it becomes even more difficult to distinguish between roles. Roles will need to be regularly modified and redefined, so the role guides need to keep up with the changes. This way, they stay relevant to the sales reps, but also act as a plan of record for the roles.

What can you do about it? Sales enablement can help by overseeing the entire role definition and creation process, making sure there are no overlaps or gaps across the roles. Sales enablement can also write the role guides, but with significant input from the sales managers, and agreement to keep them up to date and get them to new sales reps that join their teams. It is also important for sales enablement teams to maintain and modify these role guides when necessary. This also creates an opportunity for role owners to exist for larger companies. These people can be the overall owner of the role guides, and can take an active part in the creation of sales compensation plans for the roles, hiring sched-ules and procedures, subsidiary organizational structures, training, and community/culture building within the company.

82. Managing the SaleThe next major area of challenges that sales teams face is the management of the sale itself. This includes creating and executing the sales process, the methodology that your sales team will use to approach each sale, and the tools that assist your team before, during and after the sell.

Sales Process The sales process is the approach your sales team takes to initiating and nurturing sales opportu-nities. It ideally involves taking an initial conversation with a stranger and turning it into a customer relationship by closing a deal. But there is a lot going on between these steps! There are a number of tasks that a sales team must complete before moving a sale forward, and it takes some logical grouping of those tasks to keep the process organized. Organizing and grouping tasks into stages of the sales cycle and closely monitoring them is what makes up your sales process.

Why is it a challenge? It is difficult to determine and emphasize the right activities for sales reps to focus on, the right pros-pects to be selling to, the right way to sell, and the right criteria to advance an opportunity. But all of this is very important for managing pipeline and revenue. Only the most seasoned and tenured sales reps at a company truly know what activities work for that company, but fresh eyes can help identify missing or inefficient parts. Its unlikely any one person is an expert at everything and even if such a person exists, buyers and the competitive landscape are often changing the process. This poses a challenge as companies try to keep up with an evolving process while still taking advantage of whats worked in the past.

What can you do about it? By working closely with both sales operations teams and sales executives, sales enablement teams can help across the entire sales process. This occurs at the granular level by helping reps improve skills for specific activities, and empowering managers to perfect those skills. Sales enablement teams can also measure conversion rates from one sales stage to the next, and diagnose what needs to be improved to increase that conversion rate. This may include identifying and creating

9specific training, changing activities, or a combination of these. The final step is to help sales oper-ations make the process easier on the rep by training reps and sales managers on the importance and benefits of following the process.

Sales Methodology Every successful sales organization needs a plan for effectively selling that carries it through the entire sales process. But it can be difficult to choose a method, stick to it, and then modify it for your own organizations needs. A sales methodology is an approach to selling and the group of tactics a sales rep will use during the selling process. These can be generic in nature, such as solution selling or consultative selling, but there are also many branded methods, such as CEBs Challenger Sale, Craig Elias SHIFT, Jill Konraths SNAP Selling, and Neil Rackhams SPIN Selling.

Why is it a challenge? While some of these methodologies might be more tactical and others more subjective, your sales methodology must have a concise and consistent approach to all stages of the sales cycle. This includes initiating a sale, getting to and through each activity needed to advance the sale of your solution/product/service, and the triggers to recognize when its time to walk away from a deal. This means that there is a way to approach each activity in the sales process. For example, the Challenger Sale suggests that the sales rep teaches their prospect something, tailors their message, and takes control of the sale. This can be applied early in the sales cycle and can carry all the way through to closing a deal.

However, selecting, training and sticking to a sales methodology requires careful implementation and attention. An executive sponsor must spearhead it, but sales enablement teams or individuals need to make it stick. With so many approaches to selling, each with related books, blogs and vid-eos, having the sales team try new methodologies can create chaos.

What can you do about it? It is important for sales enablement individuals to help select a sales methodology for the sales organization. Carefully select one, and stick with it, while making refinements to each sales activity, sales content, and training as you go. The process can be made easier by mapping out a clear sales process first. Once the process and methodology have been set, its up to sales enablement to train everyone on the overall process, the necessary activities, and the approach to accomplishing each activity. The final step is to create open channels for sales team feedback and questions, which will help ensure proper implementation.

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Sales Tools This guide discusses a number of challenges that seem daunting for mere humans to take on. Thankfully, technology has provided us with a plethora of tools that help ease many of these chal-lenges, but the hard part is picking the right ones for your team.

Why are sales tools a challenge? While sales tools inherently make life easier for sales reps, there are so many solutions in the market and new ones coming out every day that it can be overwhelming to decide where to start. It is also important to understand how tools will be received, implemented and adopted by sales teams.

What can you do about it? Sales enablement teams should take the lead when it comes to looking at the business and deciding which types of solutions are needed, why theyre needed, what they need to do for the business, and the required features. Once these rough parameters are understood, the list of vendors should be manageable and can be evaluated for the value they bring the business. When evaluating sales tools, its useful to segment them by their functions and features. These four categories highlight sales responsibilities and give you a good place to start:

1. Who to sell to and why

Territory Management, Account & Selection Tools

Account Planning Solutions

Lead Scoring Solutions

Lead Management & Contact Information Solutions

Social Selling (account & lead insights) Solutions

Customer Intelligence Solutions

2. Managing the sale

Opportunity & Account Management Solutions

Pipeline Management, Opportunity Scoring & Forecasting

Customer Engagement & Activity Tracking Solutions (e-mails, calls, meetings, social, etc.)

3. Training the sales skills, behaviors and tools

Learning Management Solutions (LMS) (host, assign and track courses)

Coaching Solutions

Sales Playbook Solutions

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Sales Training Solutions (trainers, courses and content)

4. Sales content

Messaging and Positioning Training & Reinforcement Solutions

Content Management Solutions (CMS) (host, expose, deliver and share content)

Content Creation Solutions

Content Usage & Influence Tracking Solutions

This is clearly a very lengthy list of tools, and there are a number of solutions that do the jobs of many of these tools. For a list of sales enablement solutions, click here for Seismics Guide to the 16 Top Sales Enablement Solutions for the Enterprise.

3. Sales TrainingTraining sales reps is an ongoing process, one that doesnt stop once the rep has learned the ropes and is autonomous. Training processes make up another set of challenges that sales teams face. This includes planning and executing events such as sales kickoffs, onboarding new sales reps, and sales coaching. Because training is ongoing and the methods are constantly changing, it requires careful planning and documentation.

Sales Kickoffs A sales kickoff event usually marks the official beginning of the fiscal year for a sales organization. It involves celebrating the previous years successes, building excitement for the upcoming year, and preparing for the challenges of the year ahead. This may be a week-long event, or just a day or sin-gle afternoon. These events are a combination of work and play, and it takes a delicate balance to make sure kickoffs are productive but also fun.

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Why are they a challenge? Holding a successful sales kickoff without any hitches is a big challenge. More topics get dropped from the events agenda than end up on it, and it can be hard to make sure all important things get done in the amount of time youve scheduled. There are numerous activities that usually need to occur, such as product and internal process updates, sales skills training, team building sessions between sales and related teams, and much more. All of this could lead to a chaotic event if not planned and managed properly.

What can you do about it? The sales enablement team should start by working with sales leadership on defining the overall goals the event should help to accomplish. This will give you a baseline plan to stick to and build from. Being on the same page with sales leadership will help to execute and prioritize all of the kickoffs activities. Then, the Sales Enablement team can partner with all the different department heads (Support, Services, Marketing, Product, Partners, etc.) to get their involvement as needed. Ideally, and depending on the size of your company, you will have department heads own various parts of the event relating to their expertise. This will keep every team updated on others progress and priorities, which makes for more communicable and productive companies. Then you can focus on any skills training and/or third party speakers that may occur. It is important to always update the agenda to match the realities of each session: who, what, when, where, and for how long. When items drop off the agenda, keep track of them for future training opportunities.

Sales kickoff events are a fun way to celebrate success and update sales organizations on any and all progress or growth. But it can be difficult to keep kickoffs productive and ensure that your sales reps are receiving the training and information they need to succeed. By carefully preparing and prioritizing activities, companies are capable of holding perfect kickoff events.

Sales Onboarding As organizations grow, it is inevitable that you will be onboarding new sales reps. This can be a huge challenge for rapidly growing companies, because the onboarding process is being created and streamlined while new team members are being brought on. Enterprise organizations see challeng-es as well, whether its ensuring that all new members are experiencing the same onboarding pro-cess, or simply making sure no one falls through the cracks.

Sales onboarding refers to all of the efforts that need to take place to get a sales rep up to speed and achieve their quotas as soon as reasonably possible. This includes training, coaching, mentoring and access to the content necessary for these tasks. All of this must create a foundation of under-standing for the sales rep, with coaching and mentoring happening on a regular basis to make sure the rep is performing adequately. But most importantly, sales onboarding makes sure that reps are at the right place on the learning curve at the right time.

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Why is it a challenge? When hiring and onboarding new sales reps, you want them up to speed as quickly as possible so they can begin meeting with customers, working opportunities, and hopefully closing deals. How-ever, if you dont take the time to train, guide and mentor them properly, they could alienate great prospects or lose deals that an experienced rep would win. It is a considerable amount of work to make sure a new sales rep learns your sales process, accomplishes required activities, understands when to partner with internal teams, and acquires the skills needed to close deals. Most of the time, especially in large enterprise companies, this is done through content created through marketing and sales collaboration specifically for training and onboarding needs. Creating all of this content and the training curriculum for new sales rep takes considerable time and effort.

What can you do about it? Much of the onboarding work needs to land with new reps immediate sales manager(s), and ideally a mentor or peer to help on a daily basis. However, sales enablement teams can help by creating a Sales Boot Camp, which is a few days or weeks of training that gives the new reps a baseline un-derstanding of the company, products, processes and tools. Additionally, a checklist of topics (with accompanying documents and videos) for them to learn on their first 30, 60 and 90 days on the job can help them track their own progress. These trainings and guides should be unique for each role, such as SDR versus Enterprise-focused Account Executives.

Investing time and effort into streamlining a comprehensive sales onboarding program will save your team valuable time and money in the long run. There will be less risk of sales rep turnover, because your reps will have the knowledge they need to understand the processes and strategies your sales team uses. While organizing and executing the onboarding process seems like an extensive project, it is one that will help your team grow fluidly and with considerably less bumps along the way.

Sales Coaching In sales organizations, normal training can only go so far. It doesnt occur formally every day. Most of the time, it requires a hefty investment, both of money and time. On the other hand, sales coach-ing can happen both formally and informally, any time a sales manager observes and interacts with a sales rep, with the goal of helping that sales rep improve. The best sales leaders and managers will coach formally on a regular basis (by way of monthly or weekly meetings) and informally as needed.

Why is it a challenge? Many great sales reps figure out how to be great by simply working with and observing peers, especially in the first formative weeks when new reps are learning the ropes. However, that doesnt mean that the only learning should occur with peers. It is too easy for sales leaders to default to immediate supervisors for coaching, but it is much more effective when timed appropriately and comes from all levels of management. Further, there is a good chance that immediate managers have never received any sales leadership training, or even experience coaching while they were a sales rep. This can lead to difficult onboarding, inefficient work processes and habits, and slower

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professional growth for those being coached.

What can you do about it? One of the most important responsibilities that a sales enablement team can own is to help turn all sales managers into great sales coaches. There are a variety of studies that show how training, fol-lowed by sales coaching, will yield the best improvements in sales rep skills. Therefore, sales enable-ment teams should train sales managers to be great coaches by providing them with an easy way to keep track of and follow up on coaching topics, plus a list of themes to look for. Sales enablement teams should be available to provide guidanceboth written and verbalfor the manager and rep to refer to regarding those topics. Wrapping all of this into a coaching guide is a great place to start, but just like sales playbooks, its insufficient to just write it, hand it over, and expect to have it followed. Sales enablement teams need to regularly meet with the sales managers to make sure coaching is working, that all coaching opportunities and areasboth covered in the guide and all othersare discussed so that each manager is coaching as effectively as possible.

4. The Bigger PictureThe challenges this guide has covered so far include practical, everyday hurdles, challenges that teams face every day and that must be addressed every day. But what about the challenges that have to be carefully planned and executed before sales can even begin to sell? The following chal-lenges cover the bigger picture of sales enablement, including change management, organizational structure and sales strategy.

Organizational Structure Organizational structure is something that all companies must consider and carefully plan, especially when growing rapidly. When there are multiple large teams involved in the sales process, its impera-tive that teams explicitly understand the processes and policies that go along with the structure.

An organizational structure defines how activities such as task allocation, coordination and super-vision are directed towards the achievement of organizational goals. In sales organizations, this

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applies to how and to whom leads are distributed, who leads and supports demos, and how leads move through the buying process through different parts of the organization, among other things. Depending on the size of the company, there are many levels of organization that help to delegate responsibilities and create a productive structure. A companys organizational structure will usually have all of the different sales teams reporting up to the VP of Sales, but Marketing, Partner/Alliance teams, Services, and Customer Success all come in to play for Sales at different times.

Why is it a challenge? Not every person involved in sales processes and operations report to the same person. This means that while the ultimate goal of these teams is the same (generating revenue), each goes about it in a different way and supports sales through many different functions. It is not the primary goal of these other teams to support sales reps with sales efforts, because that is not their primary job function. This can often make it difficult for the sales reps to get the help they need in a timely manner, espe-cially in large companies.

What can you do about it? Sales enablement teams can help reps by connecting and partnering with all of these organizations when training and onboarding. It is important for organizations to have established and agreed-up-on channels for communication so it is clear who should be held accountable for certain tasks. Another way to foster collaboration among these teams is by giving sales support teams (market-ing, services, etc.) the chance to help with building and updating the overall sales process. This gives them a voice in the processes in which they are involved, and can help ensure cross-team inter-actions are documented and agreed upon from the start. The most important part of a functional organizational structure is the open collaboration it fosters.

Sales Strategy One of the first things your company did was establish its sales strategy. It is one of the pillars of your organization, and can determine whether youll sink or swim. It also changes along with your company as you grow, merge, reorganize and scale, and it can be a challenge to maintain and streamline.

Your sales strategy consists of what you consider to be your addressable market, how you plan to divide it into manageable areas, and how you plan to sell to accounts and individuals in those areas. This all includes segmentation, territories, personas, sales methodologies, and sales models.

Why is it a challenge? As a sales team grows, territories will change. As sales methodologies change, mature and improve in an organization, the reps need to adapt. When a sales organization decides to adopt a partner model to help generate leads, co-sell or resell, all reps need to adopt the model as well. Essential-ly, any changes to the sales strategy will usually result in some type of change for sales reps. Any organization that is focused on improving will regularly make improvements to some part of their

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sales strategy, but this can be challenging in larger organizations, especially if all employees arent on board.

What can you do about it? All changes to sales strategy require the sales enablement teams help, whether its to teach a new skill or process, get acclimated to a new organization structure, or shift responsibilities and perfor-mance indicators. However, since sales enablement has some involvement with all sales roles, this team has a unique perspective to help guide sales leadership. It is important to stress the impact these changes may have on the sales reps and to provide suggestions for how to manage it. Expe-rienced sales enablement managers can also offer guidance to what the different methodologies, models and elements that may need to be changed to improve the sales strategy.

Change Management Sales organizations see a vast array of changes that transform the way things are done. These changes include new sales pitches, sales methodologies, updates to the sales process and activities, updates to territories, and most importantly, new personnel. Making transitions and changes seam-lesslyand making sure they stickrequire advanced change management skills.

Change management is the approach taken to transitioning individuals, teams, and organizations to a desired future state. This includes the proper implementation of new strategies, onboarding new employees, and effectively scaling these processes when the time comes.

Why is it a challenge? From a skills or experience perspective, most employees dont have a broad understanding of all aspects of a business. So when changes span organizations, this becomes an obstacle to facilitating changes. From an emotional and psychological perspective, many people are resistant to change, so the benefits of the change need to be communicated clearly and in a manner that will win over everyone who is affected by the change(s). Finally, especially with larger companies, the actual deployment of changes such as territory shifts and methodologies take a long time to be put into effect and adopted by all parties involved.

What can you do about it? Sales enablement teams can help internally by creating and delivering guidance and training. This would be for both the sales managers and individual sales reps who are impacted by the changes. This could be as simple as a few webinars and meetings with sales managers, or it could involve modifying your CRM and business processes, creating guides or decks to share, and facilitating training and possible certification. As a sales enablement team, these are all things that can fall into the realm of managing and ensuring changes are implemented and adopted seamlessly.

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ConclusionThe sales enablement function is not an easy one. Many challenges affect sales teams every day, and it can be difficult to ensure sales teams have everything they need to sell successfully. When creating and planning your companys sales enablement strategy, whether that involves dedicating a team or individual specifically to this strategy or making it the responsibility of all sales-related employees, it is imperative that you address and tackle the above 13 challenges.

Brian Groth did so by assessing his own organization and answering the questions:

Q: How can marketing better support sales?

A: Ensure marketing contentboth internal and external documentsare up to date, relevant and easily accessible by sales.

Q: How can sales management implement the right processes for reps to sell effectively?

A: Carefully choose and develop the right processes to manage and streamline the sales method for all reps.

Q: What are the best practices for training, onboarding and coaching?

A: Involve all leadership in the training, onboarding and coaching processes, and streamline these processes across the entire organization.

Q: What organizational structure and strategy will set the sales organization up for success?

A: Each organization will have a different structure, and it will always be changing. The key is to carefully evaluate your companys needs and build your structure and strategy around these, then stick to it and allow it to evolve with organizational changes.

Any companys sales function will run much smoother by ensuring your sales team isnt held back by these avoidable hurdles. In doing so, you are empowering your sales organization to have more personalized, relevant conversations with prospects and customers, which will help them reach the ultimate goal of generating more revenue for your company. The right sales enablement strategy, when properly executed, can be the difference between missing your number and exceeding it.

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