Pipeline generation: How to write trigger-based emails that book more meetings

Boost your pipeline generation efforts and book more meetings using Will Allred's email frameworks.
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When sales trigger events occur, it creates a sales opportunity most SDRs love. But to convert that opportunity into revenue, you need the right trigger-based email strategy.

In this article, you’ll learn the top sales triggers to track and how to write trigger-based emails that can get you a meeting.

We originally spoke about how to write trigger-based emails that book more meetings at a RevGenius webinar.  Watch the full recording, including a live email teardown, or continue reading for insights.

What are trigger-based emails?

Trigger-based emails are emails you send to a prospect based on a sales trigger event that has occurred. SDRs and marketers look forward to sales trigger events because they create a solid reason for a sales outreach. 

For example, if the VP of sales at Company X complains on LinkedIn about one of their vendors, it indicates to an SDR who sells a competing product that solves that problem that they might need a product like yours.

Sales triggers show you that there’s an opportunity in the market. And trigger-based emails allow you to take advantage of the opportunity and declare your interest.

Tracking sales trigger events is one of the most common pipeline generation strategies. This means you won’t be the only salesperson who notices a sales trigger event when it occurs. 

To stay memorable in the deluge of messages your prospect will receive, you’ll need to tweak your strategy and craft an attention-grabbing email that gets your prospect to say "yes" to a meeting.

The top 4 sales trigger events you should be tracking

You can keep track of at least 30 sales triggers, but they are not equal. Some sales trigger events present higher chances of converting your prospect to a customer than others.

Trinity Nguyen, VP of Marketing at UserGems, recommends tracking these top 4 sales trigger events with the most ROI based on internal data from our work at UserGems.

Image describing the 4 sales trigger events sales teams need to track

Sales trigger event #1: New executives

A new hire, whether within or from outside an organization, indicates change. This means there’s more willingness to shake things up or improve current processes by adopting new tools and systems.

In addition, most companies expect new executives to give a performance report in three months. This explains why new executives spend 70% of their budget in the first 100 days. Within this timeframe, they’ve analyzed or are trying to analyze gaps in the business and how to close them. 

You can either be the sales rep who asks, “what are your priorities” in your trigger-based email or the proactive sales rep who shows how you can help them succeed in their role. 

Here are three tips for crafting the right trigger-based email for a new executive:

  • Look for the job description to know their KPI and objectives: This helps you align your pitch with their KPI, making it clear how your product can help them achieve success in their new role. You can find their job descriptions on job boards or via the Wayback machine.
  • Check what roles companies are hiring for: This helps you identify what the core business goal is for the company at the time and also makes your outreach relevant to the prospect. “A company hiring for engineers is trying to build for differentiation. While a company hiring for sales is aiming for efficiency and growth,” says Will Allred, Co-founder at Lavender.
  • Multithread: Multithreading is an overlooked strategy when reaching out to new executives. By multithreading bottom-up and across, you can find the team's current challenges and use the insights to add value to your outreach. “If you can offer insights and perspectives that a new hire is trying to gather, that’s a value add,” adds Allred.

Sales trigger event #2: Previous customers/prospects at a new company

Customer job changes are low-hanging fruit because it’s a pipeline generation tactic with great ROI. 

Your previous customers are 3-5x more likely to convert than new leads/prospects since they know your brand and have built trust in your product. You can quickly drive demand generation because this target audience are high-quality leads that tick the boxes for product-market fit and can champion your product in their new organization. 

To optimize your outreach to previous customers, tailor your messages based on their relationship with your company. 

For example, the value-add in your message for a previous customer in a new company could be a new/existing feature that fits a use case for their new company. But for a past prospect, you’ll want to speak to why you lost the deal. And why they should become customers now, such as more funding or being in a role where they are decision-makers.

Multithreading can also help you in this sales trigger event because the average B2B buying decision is made by six to ten key players.  And with multithreading, you provide sales-enablement assets to your champion to make it easier for them to sell your product to other decision-makers.

Tracking job changes of your past customers or prospects with UserGems is an excellent tactic for your lead generation strategies. UserGems automatically tracks customer job changes and surfaces them in your CRM as warm leads.

Sales trigger event #3: Funding

Funding indicates that a business has more funds to pursue its aggressive growth target. It also creates an opportunity to reach out to past prospects who couldn’t close a deal because of limited funds. For example, when we raised our Series A round, a company we had been in touch with shared a detailed email pitch about why now was a great time to invest in their hiring tool.

Your trigger-based email for a funding sales trigger can help you stay top of mind. Most messages prospects receive around this time will look like, “Congrats on your funding. Here’s X product to buy.” This is generic, and it’s hard to stand out with this format.

Trinity Nguyen, VP of Marketing at UserGems, recommends that SDRs read the news/press release to find out where the company is and where they want to go with their new funding. This information helps you personalize your message for a relevant and memorable outreach.

Typically, funding announcements are out ~3 months after the company receives funding. So it's important to keep your ears to the ground by connecting with others in the team besides the C-level executives, such as department heads. You can then launch longer sales sequences, giving you time to nurture a relationship with the prospect before pitching your product.

Sales trigger event #4: Mergers and acquisitions

“Due to the business climate, we’ll be seeing more mergers and acquisitions (M&A)  in 2023,” says Nguyen. “Sales reps often conduct outreach for this similar to the funding approach, but they are different.”

While funding is always great news, M&A often results in uncertainty. Will Allred, a co-founder at Lavender, notes that M&As are tricky because they can kill deals since companies are trying to merge their assets, so it’s important to be patient and wait while the dust settles.

Nguyen adds that this is different if your product can help companies manage the chaos and uncertainty of an M&A. In this case, your sales outreach soon after an M&A announcement will be relevant to your prospect.

Before sending your outreach message, read the announcement details to help you personalize your message. 

For example, some companies will continue to function separately while others merge their processes. Insights from the announcement will help you know which contacts to track and provide relevant context for your outreach.

Will Allred's essential email frameworks for getting a YES!

As the co-founder and COO of Lavender, an AI-driven sales email assistant tool, Will Allred’s best practices for writing sales emails are backed by millions of emails sent across Lavender’s users. 

His first advice on trigger-based emails is “avoid over-templatizing trigger emails.” 

While a cold email in a prospecting strategy can benefit from a template, with trigger emails, you need context for outreach. You have to personalize a trigger-based email if you want it to be relevant to your prospect. 

Will shares three flexible email frameworks to help your SDRs craft the perfect trigger-based email to book more meetings.

Here’s a breakdown of each framework:

Lavender ai tested email frameworks

The mousetrap

Framework: Observation → Curious question

With this framework, your trigger-based email starts with an observation relevant to the situation, then you add a question.

For example, an observation could be that companies hire more after they receive funding. Then you add a curious question that can lead to a conversation, such as, “Are you looking for a tool to help you find the best talents in the market?”

Your question prompts a response that can lead to a conversation.

The mousetrap + context

Framework: Observation → Insight → Implied solution to the problem via context

Under the Mousetrap + context framework, an SDR provides more background information on why they are reaching out.

For example, you can let the prospect know your company has a tool to help them find talents. “This detail can help bring the person closer to understanding the purpose of your question,” says Allred.

Will’s all-time favorite framework for writing trigger-based emails

Framework: Observation → Insight → Problem → Credibility → Solution → Conversation

This framework is more comprehensive and detailed, but still concise. 

You begin your message with an observation, provide insight, present a problem the prospect is facing, show credibility through social proof of your product, then encourage conversation. 

For example, you can mention that while most companies post on public job boards, they struggle to find skilled talent. Then you explain how one of your customers has used your product successfully. And close with a prompt that drives a response.

How to improve trigger-based emails

Watch this live email teardown to see how this trigger-based email went from basic to gold:

Will applies the following methods to improve the email:

  • Edited the message from informative to conversational by using everyday language we all use in work conversations.
  • Used his All Time Favorite framework to write the email and drive the conversation.
  • In the video, he provides two alternative endings which can be A/B tested for improved conversion rates.

Final thoughts on writing trigger-based emails

While a B2B prospecting method might focus on making the sale ASAP, trigger-based emails are the first step to building a relationship that hopefully leads to a deal.

Keep your trigger-based email conversational, build relationships by providing value, and tap into available data to create personalized emails for better results. With UserGems, you can track your key contacts and accounts for any job changes and surface them in your CRM with personalized context for a timely trigger-based email.

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