Sales Enablement Software Guide: How to build your sales tech stack

Alex Kracov
November 1, 2022
TABLE OF CONTENTs
TABLE OF CONTENT

While building Dock, I’ve had to intensely study the sales enablement software market.

This is partly because we need to understand how to position our tool in the market, but also because I’m building out our own tech stack as I lead sales at Dock.

Now, this is fun for me because I’m a huge product marketing nerd. I led marketing at Lattice before founding Dock and I love thinking about how all the tools piece together and build off each other.

To help other founders and sales leaders understand what sales software is out there—and how to match your tech stack to the stage of your company, I've put together this sales technology guide. 

Why? 

Because the sales software market is massive. Overwhelmingly so. This graphic is only a fraction of the landscape:

Source: SBI Growth (See the full-sized image here)

The point is: your head might explode if you tried to grasp the entire sales tech market before buying any software. So I've tried to simplify it in this guide.

How to think about sales enablement software

Sales enablement software is any tool that makes it easier for a salesperson to sell.

“Sales enablement” is used to refer to only three types of sales tools: content management, sales training, and sales coaching. These tools gave sales teams the knowledge and content they needed to sell.

But the shift to digital buying and selling has massively impacted the availability of sales tools, which is why I’m taking an expanded definition of sales enablement.

It’s easiest to think about the sales enablement market in four major categories:

  1. Customer relationship management (CRM): For managing customer data
  2. (Core) Sales enablement tools: Sales training and coaching, content management, and buyer enablement
  3. Sales intelligence tools: Conversation and revenue intelligence tools
  4. Prospecting and outbound tools: Email, lead generation, and social prospecting

Outside of these four categories, there’s a long tail of smaller point solutions that are narrower in scope (e.g., for contracts, scheduling, or mutual action plans).

So how can you go about adding these tools to your tech stack?

How to build your sales tech stack from zero

If you’re a new startup or sales organization, resist the urge to build out an elaborate sales tech stack from day one. 

Your growth and the challenges you encounter along the way should dictate the tools you adopt, so let your sales tech stack grow and evolve with you.

Most sales teams follow this rough structure as they grow:

  • Founder-led sales (1 person): All sales are driven by your founder(s)
  • Small team (1-5 people): A Head of Sales or founder is leading a few AEs and BDRs
  • Growing team (5-20 people): A VP of Sales and managers are hired to scale up
  • Big team (20-50 people): Sales Directors are added to manage the managers
  • Enterprise team (50+): A CRO leads several VPs and Directors

A five-person team needs completely different tools than an enterprise team—no single tech stack would be ideal for both.

Here’s a path you can follow as your sales team grows.

Phase 1: Start with a free CRM

In the early days, your focus will be on finding product-market fit and getting customer feedback. This mostly involves founder-led reachouts that don’t scale, so your sales tech won’t matter much at this point.

Start with a basic free CRM like AirTable or ClickUp—or Hubspot’s free plan. Think of it as your starter home, as it’s unwise to go all-in with an expensive CRM until you’re ready for it.

Phase 2: Adopt point-based solutions

As you start to make sales, progressively add point solutions for each step of the sales process.

For example:

  • Need to record a personalized demo? → Loom
  • Need to schedule a meeting? → Calendly
  • Need to sign a contract? → Docusign
  • Need to do outbound email outreach? → Outreach

Most of these products offer free versions or single-user plans you can use to find the right fit.

Phase 3: Invest in your forever CRM

Once you start hiring a sales team, it’s time to invest in your sales stack.

This starts with upgrading to a more robust CRM, as it will be your source of truth and a foundational system to which all your other tools will connect.

We’ll review CRMs in greater detail later, but here are some popular choices:

  • Salesforce: the standard enterprise choice. Complex to manage and set up, but it can do anything
  • Hubspot: for SMBs and mid-market. More functionality out of the box
  • Pipedrive: another popular choice with SMBs

Then, you can reevaluate your point solutions and integrate them with your CRM.

Phase 4: Solve your people problems

As sales teams scale, the challenge shifts from managing the sales process to managing salespeople. Suddenly, you need tools to help with hiring, training, and monitoring performance. 

Companies will have different rates at which they will hit and feel these pain points, but there’s software to help with each one.

For example:

Over time, your tech start should start to solidify, and efforts shift more towards optimization and building processes rather than adding more tools.

Summary: don’t try to adopt all these tools at once. Build as you go, adopting tools only once you have a pain point strong enough to need them.

Next, let’s review the four major categories of tools you should consider adopting.

📖 Related reading: Sales Hacker has examples of the sales tech stacks used by Ambition, Clari, DocSend, Intercom, Leadfeeder, and Outreach.

1. CRM: Your foundation

The foundation of any sales tech stack is the CRM. It’s where all the customer and deal data lives, and it’s the central hub that connects to all the other sales tools.

The CRM stores:

  • Core contact data
  • Demographic data
  • Firmographic data
  • People, companies
  • Your company’s history
  • Deal metrics and statuses

Because it’s the most crucial sales tool, it’s also the most crowded market. G2 has over 500 CRMs in its product listings:

There are two general categories of CRM:

  1. Standalone CRMs: Sales-only platforms for managing customer data
  2. All-in-one CRMs: Include marketing and/or customer success capabilities

Enterprise businesses with lots of integrations tend to favor the customizability of standalone CRMs. In contrast, small/medium businesses (SMBs) are better suited for all-in-one CRMs with more out-of-the-box functionality.

Millions of words have been spilled about choosing a CRM, so I’ll just give a quick overview of the biggest market players.

The Enterprise CRM Players

Salesforce—a standalone CRM—is the clear leader and the gold standard in the enterprise CRM market.

But it’s difficult to use and even more complex to set up (spawning an entire industry of Salesforce implementation partners).

That said, it’s the first platform that most other tools plan to integrate with, so it has the deepest integrations of any CRM out there. And its infinite flexibility makes it powerful once you know how to use it. 

It’s also what most VPs and account executives are used to, so it’s the de facto CRM in the market. 

Other enterprises rely on Oracle, SAP, and Microsoft Dynamics 365, but in my experience, these are less common among the new class of technology companies.

CRMs for SMBs

From my point of view, Hubspot is the next biggest player to Salesforce in the CRM market.

As an all-in-one CRM with an end-to-end suite for marketing, sales, customer service, operations, and a content management system, Hubspot caters more to SMB audiences who want to avoid fewer tool subscriptions. 

Hubspot has come a long way in the last five years. It’s more of an out-of-the-box solution and anyone can use it, but it has less flexibility—you’re mostly stuck with what you get.

Other popular all-in-one CRMs include Pipedrive, Zoho CRM, and ActiveCampaign.

Do-it-yourself CRMs

If you want near-infinite flexibility without the Salesforce price tag, you can build your own CRM using database/spreadsheet solutions like AirTable, Monday, or even Google Sheets.

They’re a convenient way to store your data and connect to other tools without locking yourself into a CRM, but they’re hard to maintain at scale.

Related reading: Sage put together a great guide to choosing a CRM. It’s from 2006, but the advice still holds up.

2. Sales Enablement Software: Helping sellers and buyers

Sales enablement software used to be about two things: sales training and content management.

But newer sales enablement software (including Dock) is expanding to also allow for buyer enablement.

Sales Training and Learning Management Systems

Learning management systems (LMSs) provide the ability to create courses and lessons for the sales team. They usually have a wiki component to them as well to crystallize internal knowledge.

These tools help with sales onboarding and education, for example, around new product releases. 

These product launch lessons can cover questions such as:

  • How do you message the product?
  • How do you pitch the product?
  • How does it compare to competitor products?
  • What assets and videos are available?
  • How does sales compensation work?

Sales enablement training systems are usually managed by the product marketing team.

Content Management Systems

A sales content management system (CMS)—not to be confused with a website CMS—is a central asset repository for sales teams. 

Marketing teams are most often responsible for managing the CMS. They create and manage a range of sales enablement assets, including:

  • Pitch decks
  • Demo videos
  • Whitepapers
  • Ebooks
  • Product explainers, etc.

Sales teams pull assets from the CMS and share them with customers. Then sales and marketing can see analytics around customer asset usage.

Old-School Sales Enablement Platforms

Until now, these two pillars (LMSs and CMSs), have been the core of the most popular sales enablement platforms: Highspot, Seismic, and Showpad.

These companies were all founded around the same time, over ten years ago (Seismic in 2010, Showpad in 2011, and Highspot in 2012). 

In general, they share a lot of similarities:

  • They offer a robust sales CMS
  • They focus on training and guidelines for sales teams
  • They’re built for big enterprises—mainly Fortune 500s
  • Their buyer enablement workspaces are inflexible and non-collaborative

In my experience, the biggest challenge with these legacy systems is their search capabilities. Because it’s hard to find content in folders, sales reps normally resort to “search” when looking for the latest training deck or demo video.

If they can’t easily search the CMS, they’ll give up.

Of the three legacy tools, Highspot is the emerging leader as they’ve innovated around the concept of “Spots” to manage content.

Instead of a nested folder system with scattered assets, Spots act as an internal webpage that hosts content around a specific theme. For example, you might create a Spot for “Compete Materials,” which hosts all competitor analyses.

Seismic and Showpad are, more so, legacy solutions, as they’re based around the traditional folder structure and have aging search functionality. (And apparently, Seismic needs Microsoft SilverLight to function.)

New-School Sales Enablement Platforms

New challengers have emerged to displace these older platforms.

In the LMS category, Workramp has become a popular sales training tool. It provides the ability to create sales onboarding boot camps, training programs, and learning centers to create consistency across your sales team.

Guru has become the popular choice for knowledge management. It avoids the search problem by allowing for the creation of collections containing boards and cards—which are bite-sized pieces of knowledge.

Guru's knowledge management structure

Each department can build its collections and boards from shared cards, so the facts can stay consistent, but topics can be organized relative to each team’s needs.

Next, we come to our product: Dock.

Dock started where other sales enablement tools were the weakest: buyer enablement.

Other sales enablement tools are built to empower sales reps. But in B2B buying, the buyer champion carries a lot of the sales burden. They have to convince internal stakeholders, research the market, and walk their internal team through complex deal stages like proof-of-concept projects or security reviews.

With Dock, sales reps can simplify this process for the buyer by providing a single shared workspace for sales content, resources, collaboration, and communication.

Dock lets you create user-friendly workspaces with embedded videos, slides, PDFs, and more.

What does this look like in practice?

  1. A sales rep creates a Dock space for a prospect with a demo video, sales proposal, mutual action plan, and other relevant content.
  2. The sales rep presents the buyer champion with the Dock space after their first demo call.
  3. The buyer champion shares the Dock space with their internal buying team.
  4. The buying team communicates directly in Dock, commenting or asking questions on specific assets and checking off to-do items on the mutual action plan.
  5. The seller can see what content is accessed by the buying team and when.
  6. The seller and buyer champion work together in the Dock space to close the deal.

📘 Dock Templates: To get a better feel for Dock, check out our library of templates for sales, customer success, and agencies.

3. Sales Intelligence Software: Collecting data

The next big category—sales intelligence software—is about collecting data throughout the sales process. This includes data about your ideal customer profile (ICP), sales calls, reps, and pipeline.

I look at sales intelligence tools in two general categories: conversation intelligence and revenue intelligence.

Conversation Intelligence

Conversation intelligence tools collect information about the conversations sales reps are having with prospects. From my point of view, this is one of the most exciting categories of new software for go-to-market teams. 

These platforms record calls, break them up into snippets, and use AI to provide annotated notes about the conversations. For example, they may say, “Goals were mentioned four times, product A was mentioned three times,” etc.

This qualitative and quantitative data helps sales managers coach sales reps and gives unique insights into product marketing and leadership on refining their market positioning. 

The big leader in this space is Gong. They have a world-class product and have seemed to beat out Chorus (now owned by ZoomInfo) as the leader in this category.

Gong's coaching inbox gives you a quick view of your feedback activity

Revenue Intelligence

Accurate revenue forecasting is always a challenge for sales leaders. In the early days, you don’t have clear benchmarks to guide you. As you scale, your close rates may differ by sales rep or product line—causing you to rely on subjective information from each sales rep.

Revenue intelligence software aims to take the “gut feel” out of forecasting to provide an accurate picture of your sales pipeline by product lines, geographies, and market segments.

These tools take your CRM data as input to provide insights on individual accounts (e.g., how many emails were received), individual sales teams, team performance, and overall pipeline health.

Clari (which also has a conversation intelligence tool) is the most established player in this space.

Gong has more recently expanded into the revenue intelligence space too—so it’s clear that conversation and revenue intelligence tools are collapsing into revenue intelligence software.

4. Prospecting and Outbound Software: Growing your pipeline

Our final major category is prospecting and outbound software—also known as sales engagement software.

These are email and lead providers that improve the productivity of outbound efforts.

Outbound Email Software

Outbound email software helps SDRs and BDRs scale their cold outreach—although AEs can use them too. These tools provide automated outreach workflows and follow-up sequences to improve the efficiency of outbound activities.

The most popular examples in this space are Outreach and SalesLoft

Lead Generation Software

These tools have massive databases of B2B contacts to help you identify potential prospects. Their data includes:

  • Firmographic data about the company
  • Demographic data about the person
  • Who you should target outbound to
  • Who are the people you’re selling to

ZoomInfo and Clearbit are the two biggest data vendors in this space.

Social Prospecting Software

You can also extend your prospecting to social media with tools like LinkedIn Sales Navigator or ZoomInfo Reachout.

LinkedIn Sales Navigator provides advanced search capabilities beyond LinkedIn’s basic search that allow you to identify ideal prospects and send InMail messages to prospects you’re not connected with. 

The tool also provides recommendations on contacts and companies to target based on your ICP.

ZoomInfo Reachout is a Chrome browser extension that lets you scrape social contact information from any website you’re browsing (including LinkedIn) directly into your CRM.

Now that we’ve wrapped up the big four tool categories, let’s move to the smaller point solutions.

5. Point Solutions: Other Helpful Sales Tools

Finally, we come to the long tail of point solutions that are smaller in scope, but each excellent at solving one particular problem. 

Here’s what I see as the nine biggest categories.

Proposal and Quote Management Tools

These tools help you create proposals and quotes, and collect signatures and payments.

CPQ (Configure, Price, Quote) tools allow sales teams to accurately generate quotes for complex products. Using a CPQ, the RevOps team creates a standardized product library with pre-programmed pricing rules. The most popular CPQs are Salesforce CPQ and DealHub.

Sales proposal tools like Qwilr, PandaDoc, and Proposify offer a visually appealing way to create a pricing quote alongside the proposed services without needing the efforts of a designer. 

eSignature tools like DocuSign and Hellosign help close deals quicker by making it incredibly easy to get signoff on deals.

Digital Sales Rooms

The quick shift to virtual selling has shifted how we build relationships with our clients. It’s not as easy to make clients feel special through Zoom calls, emails, and Slack messages.

Digital sales rooms don’t replace in-person connection-building, but they provide a space to create a personalized buying experience for each customer by gathering sales assets, content, demos, and contracts into one hub.

The old-school digital sales room options are Allego and GetAccept. These tools focus on closing deals—allowing you to present documents and quotes in the same place you collect signatures. But the emergence of the sales proposal tools we just covered makes these features less relevant.

Dock is a modern take on the digital sales room because of its focus on buyer enablement rather than closing the deal. Dock’s drag-and-drop builder makes it easy for sales teams to create a visually appealing hub with embedded content that helps your buyer champion advocate for your product internally. 

Dock's templated content sections make it easy to build a customized, yet scalable space.

Mutual Action Plan Software

Mutual action plans outline next steps for both the buyer and seller in order to close a deal.

As mentioned earlier, mutual action plans are necessary for B2B deals with complex buying requirements, such as security, compliance, and technical reviews.

Mutual action plans give the buyer a view of what they’ll need to do for the deal to go through, which helps avoid unexpected roadblocks—especially for novice buyers.

Sales reps used to manage this process with clunky spreadsheets and emails, but they’re messy and unappealing to the buyer.

Dock, Accord, and Recapped provide user-friendly mutual action plans that allow for a more convenient buying experience.

Dock's mutual action plans help guide the buyer through the sales or onboarding process.

CRM Notetaking Extensions

There’s a growing category of tools that let you take more advanced notes that are then connected back to your CRM.

Scratchpad allows you to sync a spreadsheet-like database with Salesforce to more easily update fields or add notes to prospects. Its automation capabilities save a ton of time updating deal information at end-of-quarter.

Dooly, an up-and-coming competitor to Scratchpad, lets you sync your meeting notes and to-do items directly with Salesforce. Dooly can also pull contact details from meeting attendees into your CRM.

Product-led Sales Tools

We talk a lot about product-led sales on this blog, so we had to mention a few product-led sales tools.

Here’s the big problem: CRMs aren’t built for product data. So you need a way to identify sales opportunities based on product usage.

Product-led sales tools like Pocus, HeadsUp, and EndGame let you combine data sources like your CRM and product-usage data, define what constitutes a product-qualified lead (PQL), and then automate outreach through your sales or marketing channels.

Calendar Scheduling & Lead Routing

I’m a big advocate of allowing for direct demo bookings right on your website. 

We used to have a “Request a demo” contact form on our homepage where I would follow up via email, but when we replaced it with a calendar booking system, we doubled our demo sign-ups.

Most folks are familiar with Calendly for booking meetings, but I’m a bigger fan of Chili Piper in a sales context because it also incorporates smart lead routing.

Chili Piper lets you embed a booking calendar directly on your website, qualifies the lead based on company size, and then assigns the demo to the relevant rep or booking slot based on priority.

We use Chili Piper to embed a booking and routing system on our website

Sales Demo Software

You have three options for sales demos: live, recorded, or interactive demos.

For live sales demos, I keep it simple with Zoom. It’s reliable, everyone’s already familiar with it, and you can supplement it with sales add-ons like Gong Zapp.

For live group demos, Livestorm offers some interesting engaging features like polls, media sharing, and live calls to action (although I haven’t used it myself).

For recorded demos (and sending personalized videos in general), my personal favorites are Loom, Wistia, and Gong. But there are tons of options out there, including Vidyard and BombBomb.

Here's a Loom product demo video I recorded (hosted on Wistia):

The interactive demo category is growing quickly for SaaS products—it’s especially appealing to product-led companies. They let you create a click-through walkthrough of your product (either gated or ungated).

Interactive demos are incredibly buyer-friendly, as they get a real feel for your product without signing up for a trial or talking to a sales rep. 

The most popular interactive demo tools are Reprise and Storylane. I’ve also heard good things about Demostack, Arcade, and Walnut.

Sales Compensation Software

As your sales team and product line grow, it gets far too complicated to calculate commission manually.

When you sign a new customer, when do you pay out commission? Is it when the contract is signed? What happens if they cancel?

Sales compensation software helps you understand how much commission you need to pay out and how it projects in the future.

Captivate IQ and Spiff are the big players in this space, with Everstage knocking on the door.

Competitive Intelligence Monitoring Software

Competitive intelligence tools provide information about your competitors. These tools are primarily managed by product managers, but the information they provide to sales teams is invaluable.

Crayon and Klue, for example, allow you to automate information gathering about your competitors—such as new products they’ve added or how their website has changed.

Product managers can curate this information for the sales team by creating competitive battlecards that allow for easier one-to-one comparison between your tools and your competitors’.

Takeaways

I hope you’ve found this guide helpful. I plan to keep it up to date, so feel free to bookmark it and check back in later as your company grows.

Here are a few takeaways to wrap it up:

  • Don’t try to build your entire sales stack at once. Scale it with your company.
  • Everything starts with your CRM. Choose one that allows for the right integrations.
  • Buyer enablement is sales enablement. Choose buyer-friendly tools—not just tools that help you on the backend.

We’re building Dock to make managing relationships with your customers easier, from sales through to success. 

You can try Dock for free for 14 days here.

Alex Kracov

CEO and Co-Founder of Dock. Tweeting about marketing, SaaS, and startups. Previously the 3rd employee and VP of Marketing at Lattice.