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The Definitive 2020 Sales Engagement Buyer's Guide

Taking a look at the market for a Sales Engagement Platform? Get informed, get smart, and acquire the best long-term solution for you & your business.

This guide is intended for tools that integrate with email providers to automatically send outbound sales emails.

Note that successful prospecting should include a sequence of follow ups that combine both emails and phone calls.

Sidenote: for readability purposes, we refer to Sales Enablement as Sales Automation, SEP, and/or Email Automation. 

These solutions allow users to send automated outbound emails that also be personalized at scale. These tools also track deliverability of emails, open rates, click rates, reply rates, and other important metrics. 

Here's What We'll Cover

  1. Examining the Status Quo Without an Effective Sales Enablement tool
  2. Long Term Ramifications of the Status Quo
  3. Targeted Outcomes & Organizational Advantages with Sales Enablement
  4. Mandatory Attributes of a New way to engage with Potential Buyers & Partners
  5. Validation Metrics for an Evaluation
  6. Implementation Best Practices
  7. Marketplace Offerings
  8. Next Steps

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1) Examining the Status Quo Without Effective Sales Engagement

If you’re researching the market for a new solution, your current situation can likely be described as one of the following:

Scenario #1: No Sales Engagement Solution: This is the first time a SEP is being introduced to your sales stack.

Scenario #2: Ineffective Sales Engagement : There’s an existing SEP solution in place, but it’s not meeting the sales organizations needs.

Scenario #3: Expensive Sales Engagement: There’s an existing solution in place, but it’s extremely costly and / or not scalable.

Scenario #1: No Sales Engagement Solution

When a sales team is not equipped with a Sales Engagement tool, this is how their day to day is spent:

  1. Email Creation and Delivery: sales reps have to manually create and send emails one by one which is very monotonous and prone to human error.
  2. Personalization: Reps that understand that personalized messaging can increase prospect engagement have to edit templates manually in order to deliver a message that resonates with each prospect.
  3. Data Entry: adding email communication into the CRM also proves burdensome and drains significant amounts of time.
  4. Overhead (Hard & Soft Costs): Soft costs and opportunity costs associated with lost time negatively outweighs the hard costs of paying for a tool.

Scenario #2: Ineffective Sales Engagement Solution

This is the usual daily reality for teams using an immature lead-gen tool:

  1. Email Creation and Delivery: there is a plethora of ineffective tools that have a difficult to use user interface, constantly and simply don’t fit your organizations business needs.
  2. Personalization: Most tools stop at variables. This means you can auto populate the prospects name and company but don’t offer a way to access information about the prospect or the prospects company in order to hyper-personalize an email.
  3. Data Entry: aThere are a couple scenarios here. Either the tool doesn’t have an integration with your CRM, it doesn’t have an open API, the tool isn’t on Zapier, or they charge extra for API access.
  4. Overhead (Hard & Soft Costs): A high sticker price doesn’t always mean a perfect user experience and an excellent UI. In this case, the legacy providers that charge the most are sometimes the hardest to use and implement because they are so dense with features and functionality. Or the opposite can be true, where the new startup on the block lacks functionality but has a great introductory price.

Scenario #3: Expensive Sales Engagement Solution

With an overpriced sales enablement tool:

  • The processes of implementing a sales enablement tool is expected to be streamlined.
  • However, usability and adoption can fall short since the applications are usually more complex.
  • Also consider the customer service and technical support available since legacy providers usually have hundreds of customers and cannot support all accounts equally.
  • Long term soft costs from of maintaining the tool can be easily incurred
  • Overall, high licensing and support costs can provide you a blind sense of security which long term can hold your sales organization from scaling.

2) Long Term Ramifications of the Status Quo

For each scenario, let’s explore the negative business consequences associated with not changing the current process.

Scenario #1: No Sales Engagement Solution

  • High Operational Pain: Hours of prime selling time are spent on manual and administrative work.. instead of focusing on pushing contacts through the sales process. 
  • Lack of Automation Drastically Reduces Productivity & Sales Efficiency: Imagine what a sales rep accomplishes today in several hours or days of composing and sending emails manually. Now imagine that being reduced to minutes. 
  • Maximum Risk of Missing Quota: Significantly increased odds of missing pipeline generation & revenue targets.
  • Training & Onboarding is Ineffective: Without a tool in place, creating, tracking and optimizing effective messaging will be incredibly challenging. 

Takeaway: Sky-high soft costs far outweigh the savings from not spending on licensing. 

Scenario #2: Ineffective Sales Engagement Solution

  • Moderate Operational Pain: While this is still an upgrade from not having a solution at all, unproductive and hard to use sales enablement tools will fall short for power users. 
  • Bad UI Limits Productivity & Effectiveness: When tools are difficult to navigate and users don’t take full advantage of the functionality, reps have to spend valuable time figuring out how to use the application. This long term effect the adoption of the tool and holds teams back from scaling efficiently. 
  • Increased Risk of Missing Quota: Without full adoption from the team, reps are hesitant to leverage the sales automation tool that is supposed to enable them to close more pipeline. 
  • Training & Implementation is Streamlined, but Isn’t Optimized: Not all tools offer a seamless self-serve UI or guided support. This makes onboarding and training the administrators responsibility which isn’t sustainable. 
  • Reduced Soft Costs Still Outweigh Total Cost of Ownership: When all these factors are considered, it’s hard to argue otherwise. 

Takeaway: Total cost of ownership is high despite reduction in soft costs. 

Scenario #3: Expensive Sales Engagement Solution

  • Medium to High Operational Pain: larger legacy providers tend to require more training and maintenance. 
  • Dense UI and Functionality Limits Productivity & Effectiveness: when there are tons of features and functionality it can be difficult for non-power users to use the tool seamlessly and stay focused on the task at hand. 
  • Increased Risk of Missing Quota: With sacrifices to data quality and efficiency, generating enough pipeline to hit quota still proves challenging. 
  • Training & Onboarding Burdens are Alleviated: Assuming the vendor is at a state of maturity, knowledge bases, technical support, live chat, and Customer Success should be available to alleviate the burden that is otherwise placed on admins and power users.  
  • Financial Resources & Adoption Dictate Viability: If your organization does not have upwards of $60-100k per year to invest in a legacy sales enablement tool, then you may need to look elsewhere. Further, if your organization does use one, but doesn’t adopt it because of operational overhead, then this is a large drain on resources. 

Takeaway: These tools can be integrated with the existing sales stack or replaced with effective, cost-effective solutions.

3) Targeted Outcomes & Organizational Advantages with Effective Lead Generation

The best sales engagement tool for your sales organization will comprise of features, usability, ability to personalize, and hard & soft costs associated with support and maintenance.

Here are a few examples of the business advantages you can gain along with the benefits the right tool delivers:

Advantage #1: Optimized Operational Efficiency


  • Reps no longer have to manually create or send outbound emails or the follow ups. These tasks can now be completed in seconds and emails can also be scheduled on designated dates. 
  • The email communication syncs into the internal CRM. 
  • Outbound campaigns can be filtered and sorted.
  • By leveraging reporting deliverability, open rates, click rates and reply rates, reps can optimize messaging and increase prospect engagement. 
  • One rep using a sales enablement tool can complete the job of 3-4 reps that are creating and sending emails manually. This in turn decreases customer acquisition cost and makes reps profitable, faster.

Advantage #2: Increase Sales Rep Productivity

  • Assuming the solution validates information before it enters the CRM (system of record), bad data can be removed 
  • This also increases delivery and conversion rates as the data is actually leveraged in sales outreach through a Sales Engagement Platform.

Advantage #3: Minimized Risk of Missing Quota

  • By streamlining time-draining processes and equipping the team with email automation, reps can focus their efforts on strategically engaging their prospects
  • In turn, their conversions from sent/delivered and delivered/engaged will rise dramatically. 
  • With more qualified pipeline, reps are less likely to miss quota.

Advantage #4: Minimized Financial & Administrative Overhead

  • From a hard cost standpoint, the ideal solution should scale with license count requirements & adoption rates. 
  • In terms of soft costs, a reduced burden on administrators allows them to focus more on optimization instead of adoption.

4) Mandatory Attributes of a New Sales Engagement Solution & Partner

Up to this point, we’ve established:

  • Common scenarios teams find themselves in
  • Ramifications of the status quo (not changing)
  • And targeted outcomes and advantages gained from effective sales enablement tools

Now, we can explore what product & organizational attributes it takes to get from the so-called Point A to Point Z.

While you’ll likely have your own set of required attributes, here are additional areas & questions to consider.  

Product Functionality

Let’s start with key areas for the tool itself. 

  • Configuration: Does the sales enablement tool you’re evaluating allow for a quick & easy implementation?
  • Reporting: Does the tool offer the visibility your organization needs to understand how to optimize subject lines, sales content and messaging? 
  • Usability: Are you able to perform advanced searches, apply filters, share templates, and personalize at scale?
  • Integrations: Does the solution integrate with your existing tech stack? If it doesn’t, is there a scalable workaround?

Organizational Strategy & Viability

The tool’s attributes are most important but you should also consider the organizational side of the equation. These questions are generally considered once technical fit and value has been established. 

  • “Big Picture” Product Strategy: If the lead-gen tool is being offered as part of a larger platform, what is the provider’s big picture plans?
  • Lead Generation Product Roadmap: Specifically, how does lead-gen fit into the big picture? Does it have a main role or is it just a supporting character?
  • Historical & Future Release Frequency: In other words, how fast is the provider delivering innovation? Are they releasing once a quarter? Once a month? How many major releases were delivered last year? Past performance generally indicates future success. 
  • Security & Compliance: Has the provider completed any kind of third-party security tests? What do they plan to do? Also ask yourself what your organization really needs (startups generally have lighter requirements than the Fortune 100).
  • Compelling Evidence: Has the. organization demonstrated success in the past? Are there reviews and/or case studies online? 

Onboarding & Support

Even the best tools can be rendered useless if adoption rates are low. Proper onboarding and support from your Sales Engagement vendor has the ability to deliver quicker ROI and value for all stakeholders. 

  • Support Forms: What’s offered (email ticketing, live chat, Account Manager, guided onboarding, support forums, etc) 
  • Support Costs: What is included? What is extra?   

5) Validation Metrics for an Evaluation

  • Time it takes to complete task
  • Ease of executing task
  • Cost it takes to get started
  • Onboarding time and resources 
  • Ongoing maintenance of the tool
  • Ease of use with reporting and understanding campaign results

6) Implementation Best Practices

You’ll likely have to invest time and internal resources to onboarding & configuration a tool that can integrate with your current sales process. And that’s just the beginning…

Your quickest path to ROI starts with effective change management. Here’s a few pointers to help ensure success.

  • Enlist an executive sponsor to help you allocate resources to the project
  • Make sure administrators are informed of incoming changes (they ideally should have be a part of the evaluation process)
  • Set up internal meetings for a kickoff and to review defined success metrics. 
  • As a team, be sure to. communicate any challenges or roadblocks as they (inevitably) arise
  • Once the onboarding phase is complete, maintain full adoption levels with quarterly meetings to review usage and provide supplemental training

7) Marketplace Offerings

If you’re considering adding a new Sakes Engagement  tool to your stack, you can start by trialing FoxBound Pursuit and stack-ranking vendors using our Sales Engagement & Lead Generation Scorecard. 

More options on the marketplace can be found on sites like G2Crowd and Finances Online.

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