Your First 100 Days As a Sales Enablement Leader (Part 1)

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There’s never been a better time to be a sales enablement professional. It’s a rapidly evolving discipline and many of us are “building the plane while flying it”. This rapid change is exactly what makes it such an exciting, fast-paced and collaborative industry to be part of. And there are some significant trends which point to an even brighter future – the impressive rise of the Sales Enablement Society, the burgeoning sales enablement technology space and the growing number of companies investing in sales enablement. It’s that last point which is fuelling all of this and the inspiration for this post.

It’s perhaps unsurprising that having a team whose role is to enable the sales organization and make them more successful leads to increased performance. In fact, the 2019 State of Sales Enablement report found that 79% of organizations have a dedicated sales enablement person, program or function. The role of sales enablement is to make the sales organization more productive – it accomplishes this by improving sales rep effectiveness (sell more) and efficiency (sell more quickly). Although it can be tempting, managers and sales reps cannot and should not be expected to carry this additional responsibility.

But what’s more significant is the impact a sales enablement team has on sales rep performance. The same research found that organizations with a sales enablement function have a higher average win rate (52.1% vs. 45.5%) and are more likely to achieve quota (57.3% vs. 46.7%) than businesses without a dedicated sales enablement function. It’s clear that investing in sales enablement is a competitive advantage and the numbers which support this are very compelling. Both these reasons explain why more organizations are launching sales enablement teams and investing in people to lead them.

However, as sales enablement is often a nascent function at companies, it can be difficult for newly appointed leaders to hit the ground running in their first 100 days. You only get one chance to make a good first impression, so it pays to be purposeful about the approach to those important first few months.

Here’s how to set yourself up for success during your first 100 days as a sales enablement leader.

Weeks 1-2
Get Set Up for Success


During the first two weeks at a new company, there will likely be an onboarding program where you get set up on the company’s systems, are given a laptop and get up to speed on HR policies. You will also spend time learning about the company, its vision, and strategy, various teams, as well as the product, who you sell to, the market, and competitors. This is obviously a fantastic opportunity to become immersed in the company and get set up for success, but you should also see the onboarding experience through the lens of a new sales rep. Taking this approach will help you later on if you need to tackle sales rep onboarding.

Meet your key stakeholders

After completing or, better yet, alongside the onboarding process, start meeting with the people that will be integral to the success of the sales enablement function. As a starting point this should include the executive sponsor, the people on your team, the other teams you will need to partner with and last, but by no means least, the teams you will serve.

During those meetings, aim to discover the following:

  • Executive sponsor – what’s their vision for the sales enablement function? What challenges do they see? What teams need to be enabled first?
  • Your team – what have they been doing up to this point? What works? What doesn’t? What are their strengths? What are their weaknesses? What should the team stop doing? How is the team perceived internally?
  • Partners (sales operations, marketing, competitive intelligence, L&D etc.) – what are their goals? What are their priorities? What are they working on? How can they work with your team?
  • Serving (sales leaders) – what are their biggest challenges? What are their strengths? What are their weaknesses?

These meetings will give you a high-level overview of the business and help you understand the current state of sales enablement, business priorities, and what needs to be accomplished.

Understand the current level of sales enablement maturity

Based on the meetings with key stakeholders, it should be clear what type of sales enablement function you’re now leading and its level of maturity. At this stage, it’s valuable to consider where your team is today and why that is. You should also think about where you want to get to and what it will take in terms of people, technology, and resources to achieve that.

Weeks 3-4
Understand Your Sales Organization

Meet the top sellers

The purpose of meeting top sellers is to learn about their sales process. Become familiar with the details and understand what makes a top performing sales rep tick – what behaviors, approaches, and plays lead to President’s Club performance?

To glean insights from top sellers, the following strategies are helpful:

  • Have 1×1 meetings
  • Join sales calls
  • Attend team meetings
  • Sit next to top sellers
  • Speak with sales managers
  • Run surveys
  • Host focus groups

Create learner personas

Learner personas are fictional, generalized representations of employees. They help you understand your employees (and prospective employees) better and make it easier for sales enablement to tailor programs to their specific needs and behaviors.

Create a learner persona for each role that you will be enabling. For instance, a business development rep will likely have a much different profile to an enterprise sales rep or sales engineer, and therefore needs a different person to reflect that. Craft learner personas based off interviews with employees, job descriptions, as well as your own research and analysis. At a high level, learner personas should include the following:

  • Background
  • Demographic
  • Goals
  • Role
  • Challenges
  • Frustrations
  • Personality

Once you’ve developed a learner persona, it’s time to validate them with the business. The validation stage is crucial – learner personas represent the people you will be serving and building sales enablement programs for, so they need to accurately reflect your sales organization. This exercise should be done at least once a year.

Weeks 5-6
Put the Building Blocks in Place

Apply learning science

Consider learning science and how it will be applied to your organization. The learner personas will give you insight into the people you are enabling, but you also need to understand learning science and ensure that the programs you provide match how people learn.

Back in 2014, Deloitte published seminal research entitled, “Meet the Modern Learner” – it highlighted how modern workers are increasingly collaborative, empowered, untethered from technology, but overwhelmed and distracted. These trends go some way to explaining the continued rise of microlearning, an approach based on short bursts of learning. Select an approach that is backed by research and will help your sales organization learn.

Formalize sales rep competencies

Essentially, sales rep competencies are the key skills and attributes sales reps need in order to be successful in their role. They will likely include selling motions, product knowledge, company systems, and being a good colleague.

Begin the process by meeting sales leaders and understanding what competencies they expect sales reps to develop and by when. Do this for all sales roles and levels – the more senior the role, the higher the competency level.

The table below shows a list of fictional competencies an account executive needs to develop and by what point in their tenure:

planning table

Understanding what competencies sales reps need to develop and by when is hugely important – it drives alignment so that the sales rep, their manager, and sales enablement understand what they need to work towards. Indeed, every sales enablement initiative should help drive improvement towards a competency.

Develop a point of view on proficiency

Once you have agreement on the competencies a sales rep needs, it’s time to think about the level of proficiency required. There’s a couple of ways to approach this. Automation Anywhere uses a leveling system, where level 100 is the introductory level and level 400 represents deep expertise. For some roles, reaching level 200 is sufficient, but for others, they need to hit levels 300 and 400.

HubSpot employed a different approach that used a mastery model, where sales reps were considered either learning, applying or mastering their job. Regardless of the approach to proficiency, the most important part is understanding the levels of knowledge and what sales reps need for their particular job and level.

Create learning paths

Once you understand the competencies that sales reps need to develop and to what level of proficiency, it is time to build a learning path to help them get there. Learning paths, as the name suggests, are the steps that sales reps must follow in order to develop the required competencies. While there is no set-in-stone definition of a learning path, they will likely include prerequisites, training, a practical component, quizzes, certification, and reinforcement.

Activating these steps in the first six weeks will help you set a solid foundation from which to build a successful enablement function.

Check out part two of this series to learn how to take the enablement function to the next level within your first 100 days as a sales enablement leader.

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