Sales Objectives

The Root Causes of Your Sales Outreach Failure

"Outbound doesn't work," is not a valid answer here.. Here are 5 factors that often derail sales campaigns

If your sales outreach strategy failed to deliver the intended results, there’s little room for moral victory. 

Too often, blame get’s passed around when in reality, it’s a team sport. 

Instead of theorizing about whose fault it is, we’re going to unpack the top 5 reasons why organizations fail to deliver on pipeline generation (and revenue) goals. 

This way, you’ll walk away with a sense of what you can do to bring a solution instead of casting blame. 

And to be very clear.. this is not going to be a game of pointing fingers in every direction.. (If that’s what you want, you’ll have to refer to season 6, episode 10 of The Office).

Pictured Above: Marketing, Sales, and Product After Missing a Quarterly Number

1) Reps Aren’t Targeting Their Accounts or Prospects Properly

It may sound obvious but an extremely common mistake outbound reps make is not segmenting deep enough to help create opportunities with higher quality prospects.

Research shows that most sales reps have a light understanding of their target market or have never been taught to segment properly. The negative consequences of not having a segmented prospecting approach is a lot of wasted time trying to engage unqualified leads. Strategic account and prospect selection leads to higher qualification rates which generate more meetings and ultimately more pipeline that has a higher chance to close faster and with a larger dollar amount.

Most B2B companies typically consider the following general segmentation criteria when selecting their targets:

  • Geography
  • Industry
  • Title

Reps with more experience will focus on a few additional segmentation options such as:

  • Number of Employees
  • Annual Revenue
  • Specific Companies (For Account Based Marketing)
  • Seniority Level

Top reps with a crystal clear understanding of their target market, buying windows, and ideal prospect profile will usually add a few of the following segmentation options to their strategy:

  • Technologies Used Internally
  • Last Funding Date
  • Last / Total Funding Amount
  • Company Founded Date (Age)
  • Annual Growth Rate
  • Unique Prospect or Account Keywords
  • Recent Events (Google Alerts, News, etc.)
  • Target Competitors of Their Current Customers (Case Studies For Like Minded Organizations)
  • Identify Challenges Based off of Public Information (Annual Reports)

It’s important to note that obtaining this information can be a challenge in itself and there are a variety of vendors that can facilitate account or prospect intelligence data depending on your organizational needs. If this profile hasn’t been fully defined, a great place to start would be to take a look at your top customers, identify trait patterns, and work backwards from there. If it has been defined, make sure reps are following the process to segment and send relevant personalized messaging.


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2) Unqualified Leads or a Poorly Conducted Qualification Process

Qualification is the foundation for a successful sales strategy. Unqualified deals clog the sales engine, stall pipelines, and drain the productivity of sales reps.

A proper qualification process will eliminate prospects that aren’t the right fit for your organization’s product or service. When sales reps effectively implement this process, the result to their pipeline is a quicker sales lifecycle, larger deal sizes, and higher customer satisfaction levels.

When determining if a prospect is qualified or unqualified, consider the following questions:


  • Current State – What is the current state of their organization and what type of “pain” or “business challenges” are they facing?
  • Negative Consequence – What is the negative business consequence of their current challenges? What happens if everything remains the same?
  • Future State – What direction does the organization want to go? Where do they want to be in a specific period of time?
  • Positive Business Outcomes – What is the positive business outcome that they are able to realize if they achieve their future state? Is that outcome enough for them to dedicate time and effort towards improving their current state?
  • Required Capabilities – What are the requirements they need from a product or service that will allow them to reduce or eliminate their current challenges so they can achieve their future state and ultimately their positive business objectives?
  • Metrics – How can you measure the before and after as it relates to the requirements for the prospect to know that your product or service is right for their organization.
  • Internal buying process – Does the prospect have the authority to make a deal or do they have access or influence to the Economic Buyer (the person who has the final approval from a budget and paper process standpoint) 
  • Internal buying process – When is the buying window?


Sales reps should only engage with prospects when there is the potential of a mutual fit for both organizations. If during a discovery discussion, you realize that you may not be able to solve their challenges or that the prospect may not be ready to take action, that might be a sign that the lead isn’t currently qualified or that there is no chance of sponsorship from the Economic Buyer. Failure to acknowledge this in the beginning of the sales process generally results in a rep trying to make the prospect move forward when the actual chance of the deal closing is low.

Sales leadership can help eliminate these types of challenges by offering their teams specific criteria that a potential prospect must meet in order to qualify as a fit.

3) Lack of Ownership

While sales reps are generally the first to get blamed for poor sales performance, studies show that an effective sales strategy needs sponsorship from all levels, top to bottom.

Founders & Executives

Executives have the power to shape the entire environment and culture for the sales team. This includes but isn’t limited to ensuring the right office setup, equipment, incentives, key performance indicators, and cultural expectations. Sometimes there is a lot of finger-pointing at sales reps for “quiet sales floors” but it really starts with execs for not driving the behaviour they want the team to have.

For example, leaders can sponsor spiffs and ways to rewards high performers to motivate reps to overperform. It’s important for leaders to focus on metrics that lead to quality activities versus quantity.


Frontline and mid-level managers have the unique position to drive positive and lasting change. If executive leadership isn’t sponsoring the right behaviour, managers and directors should instead take matters into their own hands.

Instead of falling victim to CRM dashboard-monitoring, try jumping in the trenches with your reps and push on leadership to give you the support you need to in turn support your team.

Account Executives

Even Account Executive’s with marketing’s full support for their segments and SDR’s at their disposal should still take ownership for their pipelines and spend some portion of their time working on prospecting activities.

This is a fact of life that’s widely accepted by top performers, but commonly deflected by “busy” sales reps who neglect things like pipeline generation for other non-revenue activities. It’s the salespeople who fall into the category of spending 65% + of their time on administrative work that typically fail at obtaining quota.

Sales Development

A Sales Development Rep’s core job is to generate pipeline so this may seem obvious. Again, let’s be clear that their focus should be on quality prospecting. No SDR should be getting awards for sending insincere, sloppy emails on a weekly basis. It’s incumbent on leadership to make sure the metric in place motivate reps to perform quality work. 

4) Irrelevant Messaging

The two most common complaints that prospects share about sales people is that:

  • Sales People don’t listen
  • Sales People don’t understand my business

It’s an unfortunate sales tendency for reps to talk about themselves or pitch features and functionality rather than spend effort to understand a business and explain how their offering can help solve challenges to drive positive business outcomes. 

Understanding the positive business value that your product or service provides is crucial in drafting the messaging you are going to use in your outbound campaigns. Real outbound B2B prospecting professionals don’t speak in features. They’re experts who listen first and then can articulate the value they provide to similar clients while operating with a focus on building business relationships based on trust and experience. 

As a sales rep, you should have some idea of the value drivers your product or service provides. 

While these vary by organization, they typically fall within 4 categories:

  • Cost Reduction / Optimization
  • Increase Efficiency / Productivity / Speed
  • Mitigate Risk
  • Increase Competitive Advantage

These are simply the four main trunks and are not all inclusive. Depending on your product or service, these can be branched in a variety of ways. A great exercise is to get your team together to brainstorm and review each value category so new and senior reps are equipped with the messaging they need to engage prospects.

5) Lack of Productivity Tools

In our lifetime there will always be a need for sales reps who can prospect intelligently and properly run a sales process from start to finish. Companies spend a large percentage of overhead hiring the best reps money can buy but traditionally fall short on enablement, whether it’s proper training or sales productivity technology. 

With 62% of a sales reps time being spent on non-revenue generating activities, the hard earned revenue a company invests in hiring top tier talent is often sabotaged by daily tasks that take up the time a rep should be using to sell.

This doesn’t mean that sales productivity technology is going to completely replace humans, however these types of tools can certainly de-complicate many repetitive tasks so sales reps can focus on driving more revenue.

In the world of sales, productivity tools are used to:

  • Search and find targeted accounts by leveraging data sources like LinkedIn or Crunchbase
  • Find and validate email addressed in seconds that otherwise would take hours to manually verify
  • Send email follow ups automatically – eliminating the manual work of sending those emails one by one
  • Help personalize email communication at scale to increase prospect engagement
  • Log activity in your internal CRM with the click of a button to ensure all communication is logged in one place

Audit your internal sales activities and find a balance between what technology can do better and faster versus what a human should focus on to maximize revenue results.

Newflash people. The year is 2020. If you’re not enabling your sales team to take advantage of automation platforms or other productivity tools to maximize results, it’s likely your competitors are.  

Next Steps

Failing to execute even one of the above topics could be holding your sales organization back from reaching its full potential. If you have identified more than one thing holding your team back, try not to change everything at once but rather focus on optimizing one piece of the puzzle at a time in order to get the team to accept and adopt the changes. Once implemented, move onto solving the next issue.

If this article brought you value, consider signing up for our blog where we release curated sales content to sales reps and leaders across the world on a weekly basis.

Monica Marino

Monica Marino

Director of Operations and Business Development

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January 9th, 2020

Zach Sergio

Zach Sergio


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