A buyer visits your website, requests a demo, and buys a few days later.This clean, linear funnel rarely happens in real B2B sales.

However, people discover and buy new SaaS subscriptions through a much messier process that looks more like this:

• The lead hears about your product in a blog post that a coworker shared in Slack.

• Then, they read another blog post a week later.

• They follow the company on LinkedIn shortly thereafter.

• Maybe, they subscribe to your newsletter.

• They get busy.

• Then, they change jobs.

• A coworker at their new company mentions that they used your product at a previous job and loved it.

• They sign up for a free trial.

• Eventually, they become a paying customer.

Snapshot of data from UserGems "How did you hear about us" form.

This is how most B2B buyers actually discover and purchase software. The more friction in adoption, the harder you'll work to close the deal.

Multiple touchpoints, messy attribution, and lengthy sales cycles create pipeline anxiety. In this post, we’ll go over some of the most common challenges sales teams face today with pipeline generation and how they can overcome them.

What is pipeline generation?

Pipeline generation is the process your sales and marketing teams use to generate enough leads to grow your business.

People often mistake sales pipelines for sales funnels. Here's the difference. A sales funnel represents the buyer’s journey whereas the pipeline reveals the steps taken by the sales team. Within the sales pipeline, your teams generate leads through a process called pipeline generation.

Your pipeline should address the 3 main parts of the buying process:

• Awareness

• Consideration

• Decision (or conversion)

You need a strategy at each step to move buyers toward conversion.

For example, in the decision phase, one of your pipeline generation strategies might be to send a proposal to the prospect. The more complex your product, the more involved your pipeline generation steps will likely be.

Why is it so hard to keep your sales pipeline full?

Since the buying process is not linear, this poses some real challenges for keeping your sales pipeline full and healthy. Here are the most common reasons your pipeline generation strategy isn't filling up.

1. Unpredictable changes in the buying process

Sales reps today face unpredictable buying processes, unlike the past when they could predict and participate in most stages.

Dark social and online word-of-mouth happen outside your view, so reps miss key buying stages.

Dark social refers to communications that happen through private social media messages and chat apps that aren’t accessible to the public, search engines, or salespeople. An example of a conversation on dark social would be two coworkers chatting on Slack about which CRM software they prefer.

These conversations remain invisible to marketers, even when they involve their product or company.

When parts of the buyer journey occur on dark social, you can’t readily track them or know how your pipeline applies.

You can help shape the perception of your brand by arming your prospects with helpful content, such as buyer's guides, case studies, and blog posts, that clearly demonstrate how your product solves a specific pain point they are experiencing.

2. Outdated leads and information

A database full of bad data or dead leads is useless.

Trinity Nguyen, VP of Marketing at UserGems, says, “30% of CRM contact data becomes outdated every year. Most revenue teams admit that their ‘CRM is a mess!’ This causes distrust in the data and teams wasting time manually looking for buyers to reach out to.

“Working with only one prospect for a deal increases the risk that your solution will lack the company-level criticality needed to secure budget approval. Your contact might get a new job midway through the deal, which means you would have to work the account from ground zero all over again.”

“The result? Sales reps and SDRs spend two-thirds of their time on manual tasks like looking for and researching buyers. This means less time to actually sell.”

Keep your data clean and prospect consistently to avoid these problems.

Regularly remove dead leads to keep your pipeline running efficiently.

Distribute this maintenance work regularly throughout the year.

You’ll want to regularly weed out the bad leads so your sales team can focus on the prospects that are the most likely to convert to paying customers.

5 ways to boost pipeline generation

These challenges create real pipeline anxiety for SDRs, AEs, and sales managers. Here's how to fix them.

1. Always be prospecting

Many sales teams focus too heavily on existing leads and neglect new prospects.

This happens most when teams are short-staffed or hitting quota.

You must maintain consistent prospecting efforts, especially when things are going well.

Stop prospecting and you'll have no new leads when current deals close, creating pipeline anxiety across your team.

Track job changes for both leads and current customers to keep your pipeline full. If someone bought from you once and changes jobs, they're likely to buy again.

In addition, here’s a strategy that our sales team uses at UserGems.

Kenny Powell, Senior Account Development Representative, says, “The best prospecting techniques revolve around being authentic. ‘Show me you know me’ is a great philosophy to live by for this.

1. Live where they live — are they active on LinkedIn? Do they prefer email? Calls?

2. Do your research before reaching out. How will what I say resonate with them?

3. Ask yourself, ‘am I solving their problem?’"

“Taking a multi-channel approach to prospecting is key. Hit your prospect with a LinkedIn follow, do your research on their page, send an email related to what you found out, and then give them a call — leave a voicemail talking about the email you sent over.

“Give your prospect a way out. Their priorities may have changed, so continuing to try and book a meeting or get a response by asking the same question over and over again will be pointless.”

2. Create engaging content

Create content that solves prospect problems. This builds trust and generates leads.

Address the specific challenges your customers face and show how you solve them.

For example, if you sell CRM software for real estate agents, you might create a blog and video series highlighting the top ten sales tactics that are working today for real estate agents.

However, sometimes something as simple as a dark social screenshot can go a long way.

For example, Taylor Vo, Senior Account Development Representative at UserGems, says, “I once screenshotted a tweet posted by a prospect and sent it to them in an email. It’s eye-catching, shows you’ve done your research, and helps to get a conversation started. The most important part here... make sure it’s timely! Sending a really old post might rub them the wrong way.”

3. Develop a follow-up process

Standardize your follow-up process so no lead falls through the cracks. You’ll want to make sure the entire sales team uses the same follow-up system.

Use your CRM to manage this process. Make sure to add every sales rep and assign follow-up tasks for each lead to make sure every prospect is contacted using the same process.

For instance, here is what our process looks like at UserGems.

Krysten Conner, Enterprise Account Executive, says, “For follow-up, we always add value with every interaction. We should add value every time. We should send content that they would willingly pay money to receive.”

Conner continues, “Things like exec. summaries of Harvard business review articles, resources that are plug and play, insights on what is going on in their industry or with their competitors. From prospecting to follow-up, we center everything on them and their needs.”

Vo adds, “I find my best follow-ups are the ones where I’m sharing relevant articles, insights into the problem, and persona-based case studies. My favorite type of ‘bump’ addresses timing concerns right off the bat. If you know the primary reason folks delay taking a demo, address that concern upfront. Call it out from the get-go, and explain why it might be worth taking a look at this time.”

4. Retarget leads and various buyers

The buying journey isn't linear and requires multiple touchpoints. Retargeting automatically serves ads to remind leads about your product. According to Google, "Combining retargeting ads with the other advertising you already do can help you sell 50% more."

For instance, when previous buyers join new companies, you should retarget and bring them back into the funnel as new leads for prospecting.

Read More: Reach previous customers at their new company with this email nurture campaign.

5. Use pipeline generation software to act on your insights

Review your sales data and act on it with automated playbooks and pipeline generation software. These help you:

• Increase your sales pipeline flow

• Make informed decisions about future pipeline generation strategies

Evaluate and adjust continuously, no matter which pipeline stage you're reviewing. Keep your process fresh.

For instance, let’s say that you have a decent email open rate. You should still be striving for better and reviewing the numbers associated with your email open rates. If you notice more people open your sales emails if you use their first name in the subject line, then you can use this information and add names to subject lines moving forward.

Or, if you see that your “About Us” page is the most popular page on your site, optimize it such that the prospect can easily connect with a sales rep.

Avoiding pipeline generation pitfalls

The evolving sales funnel demands consistent prospecting and follow-up from your reps.

You must engage every prospect for maximum pipeline health.

Otherwise, you'll have few leads and serious pipeline anxiety.

Avoid some of the most common sales pipeline pitfalls, such as:

• Forgetting to prospect when you get busy

• Not creating a system to follow up with leads

• Letting your lead lists get stale and outdated

• Not reaching out to leads and customers when they change jobs

You control your sales team's inputs, like how often they prospect and whether they stay in touch with leads and customers when they change jobs.

That’s where UserGems can help. Whenever your leads or customers change jobs, UserGems adds them into your Salesforce as new leads and enriches them with new contact information, so you can sell to them again. It’s completely automated and fully integrated with Salesforce. The system integrates seamlessly with your existing processes. Reps continue using their familiar tools.