How Workfront’s Prospectors Heavily Tailor Their Initial Email Outreach

It’s the question every sales development leader, at some point, must answer: how personal should our team’s emails be?

It’s the question every sales development leader, at some point, must answer: how personal should our team’s emails be?

It’s a huge consideration – the more personal your outreach is, the more persuasive your prospecting will be. In no uncertain terms, that is a positive. But, personalization takes time, and the more time your team spends writing tailored notes, the less volume a prospector can execute. Over time, that potential drop in numbers will affect the amount of pipeline your team generates.

It’s a tough one.

At Utah-based Workfront, a company selling modern work management software to enterprise clients, the answer has been to hyper-personalize its initial emails to a prospect. Although it does take more time to execute, tailored emails are the means by which their company “cuts through the noise” and separates itself from the avalanche of other tech companies sending emails, and making calls every day.

“Obviously, people get hit up a lot. I feel it every day, I get them a ton of emails. But, email still works, if you do it right,” says Justin Hiatt, Vice President of Digital Sales at Workfront.

“We have all seen different approaches to email, as the spray and pray approach, for example. We feel that is what has contributed to the noise. So, we have made a decision to hyper-personalize at least the first touch. That is your foot in the door, and what people see first. We feel it is the right way to get Workfront’s messaging through, and how to share our value because we believe we have something that can help.”

The road to personalization

Workfront hasn’t always enjoyed such a precise, dedicated philosophy in their prospecting. In fact, getting to a place where they decided to invest in hyper-personalizing their prospecting came as a result of trial and error.

The earliest incarnations of Workfront’s prospecting, for instance, was entirely automated. But, the broad approach resulted in dismal response rates and deliverability issues. In response, management decided to try the opposite, and prospectors were directed to personalize every touch point along a cadence. Unfortunately, that more labor-intensive method meant Workfront’s reps were unable to finish their daily activities.

“The cadence was broken. There is a balance between personalizing, and getting enough touchpoints down and complete the motion. So, that’s why we moved to hyper-personalizing the first touch and then having more automated sequences happen, as our people are making calls,” says Hiatt.

“It’s just a balance that works for us. We are committed to personalizing the first email to every person we want to talk to.”

The importance of research does Workfront personalize its initial emails? How has the company figured out how to tailor is outreach at scale, and avoid having its reps fall behind on their cadences?

It all starts with research.

“We emphasize this pretty heavily. Don’t reach out, if you don’t know why you are reaching out. Why are you going to talk to someone, if you don’t understand how you can help them? So, we leverage LinkedIn, Sales Navigator, a lot to understand the organization, and the people we wish to connect with,” says Eddy Morris, Enablement Manager at Workfront.

“We also use it for trigger events, sometimes called a compelling event, that impacts an organization or a prospect. This will tell you what is going on there, and how that relates to the value you can provide them.”

Trigger events, according to Morris, can be a number of things:

  • Job change (promotion, job change)
  • IPO, new product launch
  • Speaking engagements (that your prospect participated in)
  • Blog posts (that your prospect wrote)

“That is a powerful gesture, showing people you have taken the time to see that you are looking and understanding what they do,” adds Hiatt.

“We have a better shot at connecting is we reach out with that trigger, for sure.”

Of course, finding a personal trigger event for every single prospect is a tall order. In the event that a Workfront rep can’t find a personal event to use in their outreach, they turn to use company news – that could be the IPO or new product launch mentioned above, or a noteworthy new hire. Finally, should the company not yield any triggers, Workfront reps use important industry news such as new legislation to personalize it’s messaging.

“Everything is a balance, you can’t spend hours and hours creating a book report on an organization, or a person,” adds Morris.

“But, of course, that can be challenging. What we have found, though, is that you can always find some kind of trigger if you know where to look.”

(Editor’s note: we chatted with Tuka Das, CEO of Halifax’s LeadSift, a while back about how he uses trigger events to anchor his prospecting. You can read about it here, or listen to the interview here.)

Crafting an email

Once you’ve done the research you can actually start writing emails.

To make that process as efficient as possible – remember, hitting daily activity numbers are important – Workfront has developed a five-step template for crafting tight, tailored emails.

The pillars of that template are:

  • A tight introduction (this is where you leverage your trigger)
  • Transition the (lead into the value prop)
  • Value proposition
  • Conclusion (this is where you ask for a meeting)
  • Writing your subject line (Workfront suggests doing this last, so their reps aren’t boxed in by writing subject line first)

“It’s easy to learn and easy to digest,” says Hiatt.

‘And our are faster and more efficient with it. We do it for calls, emails, and target account reach outs.”

And what does a great Workfront email, based on this template look like? Here’s just one example:


I loved your recent talk at [X Conference]…the analogy you used to hit home, as putting out fires in the workplace is exhausting and unfortunately part of every team’s day to day. You had some great insights into enterprise work management challenges, aligning and communicating, prioritizing projects and then tracking and reporting those deliverables. I was curious how these challenges currently are affecting your teams at Company X, and I think it would be valuable to begin a dialogue about Workfront.

Workfront is a modern work management solution that centralizes all internal projects and workflows into one platform, which enables teams like your to organize, prioritize, and track all work from one place versus multiple, disconnected tools. Because everything is centralized across teams, projects won’t fall through the cracks and come back to haunt you, and you won’t spend much time putting out fires.

I’d love to connect for 10-15 minutes when you’re available over the next few days to see how you currently use the principles from your talk within your organization and see if we can help. I have time tomorrow or Friday, which works better for you?


The response to this email was awesome – the prospect called it “by far the best email they had ever gotten.” And Workfront got a meeting out of it. That’s the power of personalization. That’s the power of research. It just needs to be done in a scalable, efficient way.

For more on Hiatt’s and Morris’s thoughts on prospecting – including details on Workfront’s cadence and SDR workload – check out the rest of their interview on The Predictable Revenue Podcast.

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