Building Your Sales Enablement Technology Stack

One of the most significant trends over the past decade has been the explosion in the number of companies in the software as a service (SaaS) industry. Today, there’s SaaS products to support virtually every business function, and increasingly for specific segments too.

Several forces have combined to make this a reality - chief among them is the mass migration to cloud computing from on-premise software, and the fact that it’s never been easier, quicker or cheaper to launch a SaaS company. In short, Marc Andreessen has been proved right, and his assertion that “software is eating the world” has well and truly come to pass.

Another significant trend is the widespread consumerization of IT - functional business leaders have displaced chief information offices (CIOs) as the main buyers of IT and software products. The role of the CIO has evolved and become increasingly decentralised - CIOs now advise, guide and empower, rather than directly make purchasing decisions (although, they retain the important power of veto). The new role they play is different, broader and more impactful.

As a result most departments now have budget earmarked for software, so that they can build their own technology stack. Traditionally, a “technology stack”, was the technology used to build and run one single application, but in recent years it has expanded to encompass the technology used by a team, department or company. Under the hood of every successful SaaS company is a stack of tools which power their teams.

The chart below shows the sales technology landscape - there are over 800 vendors listed and 38 different categories. With so many tools available, third-party review websites, such as G2 Crowd, TrustRadius and Capterra have come to prominence. And just as people browse reviews for everything from restaurants to films to jobs, they also seek reviews for software. Seemingly, we humans leverage social proof to aid decision-making in both our personal and working lives.


Source: Sales Hacker

It’s fair to say that the sales enablement category has mirrored the impressive growth of the sales technology landscape as a whole (up and to the right). There are now many vendors selling excellent products, and I’m fortunate that in my role I regularly get to speak with them. This front row seat gives me the opportunity to research, demo, trial, evaluate, purchase and ultimately, rollout sales enablement tools. I also make time to read analyst reports, speak with industry colleagues, follow venture capitalist (VC) activity and generally, try to keep up with the rapid pace of change that’s happening within the sales enablement space.

As a result, I’ve been thinking long and hard about what a sales enablement technology stack should look like and the types of challenges it should solve.

The growth of sales enablement
But before we get into the detail of the technology, let’s back up a little and talk about sales enablement. In my mind, there’s never been a better time to be a sales enablement professional. The role is rapidly growing and it’s a new frontier of sorts. And there are several signs which point to a promising future - the rise of the Sales Enablement Society, level of VC funding flooding into the category, the growing number of sales enablement tools, and, the increasing number of sales enablement teams and practitioners.

According to Aragon Research, sales enablement technology is expected to be a $5B industry by 2021. If you require one piece of data to explain the large influx of VC cash in the sales enablement category and the emergence of sales enablement tools, then this is it. The market conditions are hugely attractive - increasing numbers of sales enablement teams are launching, their budgets are growing, most are using outdated tools and there’s no category leader. There’s a big unmet need.

What is a sales enablement technology stack?
There’s currently no agreed upon definition of what constitutes a sales enablement technology stack is, however, I think the description below effectively sums it up:

“A sales enablement technology stack is a grouping or “stack” of technologies that sales organisations leverage to conduct and improve their activities. Often, the focus of these tools and technologies is to increase sales rep effectiveness, efficiency and productivity, so that they are equipped to sell.”

Sales enablement technology categories
As I’ve mentioned there’s a plethora of tools which fall under the vast umbrella of “sales enablement”, however, in order to construct a technology stack, I think it’s helpful to first consider how, when and why sales reps will leverage specific tools. For example, it’s likely a sales rep going through onboarding and wanting to learn about pricing will have different needs to a tenured sales rep looking for a sales deck - so it stands to reason that they will also use different tools.

Sales enablement is often poorly defined and subsequently misunderstood, so there’s many technologies which are positioned as sales enablement. Broadly speaking, I think there are eight categories of product that can legitimately be described as sales enablement technology (I’ve also included “miscellaneous”, as there’s always new and peripheral technology, which can be applied to sales enablement). These tools all have different use cases and can be the building blocks of a sales enablement technology stack at your company.

The sales enablement technology categories are:

  • Customer relationship management (CRM)

  • Learning management systems (LMS)

  • Learning reinforcement

  • Sales coaching

  • Sales readiness

  • Sales productivity

  • Sales engagement

  • Sales asset management

  • Miscellaneous

Before we progress any further I’m keen to stress that there’s often huge overlap between the categories. Very few tools play in just one area, so you won’t need to go out and buy eight new tools. For instance, some sales enablement tools have learning reinforcement, sales coaching and sales readiness functionality as standard, while others lean heavily towards sales productivity and sales engagement.

However, I do believe it’s important to broadly categorise sales enablement technology. This makes it easier to see where it fits within your technology stack - otherwise you can feel like you’re going around in circles (as the chart below shows) or playing the dreaded game of buzzword bingo.


How to Start Building Your Sales Enablement Technology Stack

To bring some order to the chaos that is buying sales enablement technology, it’s valuable to think about the moments when a sales reps will use the software. In my experience, a good starting point is during a sales rep’s onboarding, which is typically between one and four weeks and the ramp period which starts when onboarding ends and often lasts up to six months. Thirdly, you should also consider the period when sales reps are fully ramped and selling. There’s lots happening at these different milestones and sales reps will likely need different tools.

The chart below shows the different categories of sales enablement technology which make up a sales enablement technology stack and at what stage they will be used:


Sales enablement technology explained
Below are explanations and examples of the different types of activity you would expect each type of sales enablement tool to help you accomplish:

A CRM helps businesses track interactions with prospects and customers. Sales reps can typically send emails and make calls within their CRM, as well as add notes and track deals from start to finish. A CRM is a critical business tool and is used to provide detailed reporting and forecasting to business leaders, and is often a company’s system of record.

At many organisations the CRM is owned by a business operations team, however, an increasing number of sales enablement teams are taking on this responsibility. I’ve included CRM within this post for that reason, plus the fact it is often the foundation on which other tools sit.

A CRM typically helps businesses:

  • Track deals

  • Manage pipeline

  • Log activity

  • Communicate with leads and customers (calls and emails)

  • Report on activity

An LMS is a tool to help employees learn through a variety of methods. Leading LMS products enable businesses to provide everything from instructor-led training (ILT) right the way through to online learning and just-in-time learning (JIT). An LMS provides sales reps with customised learning paths based on their role, experience and tenure and often has the means for companies to reinforce learning through quizzes, as well as track proficiency and award certifications.

An LMS typically has the following functionality:

  • Customised learning paths

  • ILT and JIT

  • Quizzes and certification

  • Analytics and reporting

  • Mobile functionality

Learning reinforcement
As its name suggests, a learning reinforcement tool enables employees to retain what they have learnt. This is important as there’s a large body of research which shows people forget what they’re been taught without repetition, reinforcement and practice (up to 90% of information can be forgotten within 31 days). A learning reinforcement tool typically takes a microlearning approach, which helps people retain only the most important parts of a training session.

A learning reinforcement tool typically has the following functionality:

  • Spaced reinforcement

  • Microlearning

  • Quizzes and certification

  • Analytics and reporting

  • Mobile functionality

Sales coaching
Sales coaching tools helps sales reps improve key competencies, such as perfecting an elevator pitch, articulating a value proposition or delivering a demo. They work by providing a test environment, where sales reps can practice and managers can grade the sales rep and provide structured feedback, all of which is tracked within the tool.

Sales coaching tools typically let sales reps make recordings or upload live calls to the tool for feedback, and some of the leading vendors use machine learning and artificial intelligence (AI) to transcribe recordings and provide coaching recommendations to the manager.

A sales coaching tool typically has the following functionality:

  • Coaching platform

  • Call recording

  • Call insights and recommendations

  • Best practice library

  • Video challenges

Sales readiness
A sales readiness tool helps sales reps to prepare for selling, and is often used for onboarding new hires and during the ramp period. The leading solutions enable people to participate in both online and ILT, discover the latest updates and receive coaching. Another benefit of sales readiness tools is that they allow you to meet the needs of the modern learner (overwhelmed, mobile and distracted) with a microlearning or JIT learning approach.

An example of a JIT approach would be a sales rep trying to create a quote within your CRM. They may have covered how to do this in their onboarding, but by the time they need to create a quote, they may have forgotten what they’ve learnt. A sales readiness tool can provide JIT learning in the form of a short “how to” video and text instructions on creating a quote.

A sales readiness tool typically has the following functionality:

  • Microlearning and JIT learning

  • Sales playbooks

  • Quizzes and certification

  • Analytics and reporting

  • Mobile functionality

Sales productivity
A sales productivity tool helps automate low value tasks - freeing up people’s time to focus on speaking with prospects and customers. There are many sales productivity tools out there, and they typically reduce the time that sales reps spend on repetitive activities, such as sending emails to prospects and setting up meetings. Advanced tools help sales reps spend their time more efficiently with intelligent notifications, such as when leads visit a web page or take a high intent action.

A sales productivity tool typically has the following functionality:

  • Email sequences

  • Meeting scheduling

  • Lead notifications

  • Email tracking

  • Workflow automation

Sales engagement
Sales engagement tools help sales reps to connect with people in a more effective way. These tools are particularly prevalent among SaaS inside sales teams that are chasing relatively high volume, but low value deals. Sales teams in that type of environment require a highly engineered and repeatable sales processes - and these tools often make it possible to accomplish that.

The best sales engagement tools provide personalisation at scale and they leverage data to identify what makes a successful connection, such as time of day, subject line and type of communication. There’s often a big overlap between sales productivity and sales engagement tools.

A sales engagement tool typically has the following functionality:

  • A/B testing

  • Email templates

  • Email scheduling

  • Text messaging

  • Video functionality

Sales asset management
A sales asset management tool helps sales and marketing teams to share the right content with the right audience at the right time. Best of all, sales asset management tools provide detailed analytics - so you can understand what content is consumed, shared and ultimately, what helps win deals.

A sales asset management tool typically has the following functionality:

  • Content management

  • Content recommendations

  • Content personalisation

  • Compliance and restrictions

  • Content analytics

There’s a large number of tools out there which can be used for sales enablement, but aren’t necessarily positioned as such. My advice is to keep your eye on the sales enablement and peripheral vendor space, and keep some budget aside each year for potential projects.

Over the past 12 months, I’ve been interested in tools in the following spaces (I believe they are worth investigating further):

  • Sales rep knowledge base

  • Digital adoption platform

  • Chatbot

  • Data enrichment

  • Meeting intelligence

  • Pipeline automation

Building your sales enablement technology stack
Each company will have its own needs and requirements when building a sales enablement technology stack. However, I believe there’s a repeatable process you can follow to ensure you’re building a stack that truly meets the needs of your sales organisation. The steps are as follows:

1. Understand the jobs to be done
Before making any technology purchases you need to understand the key activities your sales reps undertake (e.g. book meetings) and what the intended outcome of the activity is (e.g. close deals more quickly). This will give you a baseline to understand what they’re doing and what could be improved.

2. Audit existing technology
You should audit your existing technology, and seek to understand what it does, how it’s used, as well as its strengths and weaknesses. By understanding the jobs to be done and tools currently used, it’s then possible to identify gaps that new technology could fill.

As an aside, I’ve worked in organisations where it’s been difficult to audit technology (many tools were being paid for, but not used), so this may also be an opportunity to put some rigour around future technology purchases.

3. Define your needs
Next up is defining your needs, and listing at a high level what you want the tool to do for your business. At this stage my advice is to think about the outcomes and what results the tool will help you achieve. Once you’ve defined these high level requirements, you can then think about features and functionality.

4. Agree what functionality is essential and what is nice to have
Now it’s time to get granular. You need to decide what features and functionality are essential and those which are only nice to have. Be warned - people can often be swayed by nice to haves, but they’re often a distraction. To combat this I suggest creating a scorecard that is weighted heavily towards what is essential.

5. Evaluate vendors
You’re now ready to reach out and start speaking with vendors. I suggest involving key stakeholders and end users in the evaluation process, if they’re not already. Buying technology is one thing, but successfully rolling it out is quite another. Involving the right people early on, being thoughtful about communication and gaining “buy in” is hugely important.

There you have it. That’s how I’m thinking about the sales enablement technology space. While, there’s much to be positive about, I want to conclude with a word of caution. As the role of sales enablement continues its ascent and more technology becomes available, it’s going to become even more important that we remain strategic about the purchases we make and the value they help us create. Evolving from a tactical discipline to a strategic one is how we’ll gain a seat at the top table.