1. Email Marketing

How HelpScout built a super effective newsletter welcome series from scratch.

For those unaware, Helpscout is one of the largest customer support software providers in the world. They’re used by countless companies including GrubHub, Basecamp, Buffer, Trello…the list goes on.

Helpscout’s main products include helpdesk, knowledge base and live chat software which all help to meet the company’s overall goal of making customer support interaction both more humane and more helpful.

Their email list, much like their company, has been growing like wildfire. As a result, Helpscout quickly realised that they needed a reliable and repeatable way of warmly welcoming and engaging with every one of the hundreds of new people that signed up to their email list weekly.

There was only viable option, constructing a custom newsletter welcome series from scratch.

In this article, we’re going to breakdown the precise welcome email series Helpscout built from scratch for their new subscribers and even go as far as analysing the individual emails in the series.

This is invaluable learning. It’s not often you get to peek behind the curtain and see how a successful, fast growing software company constructed a system for successfully engaging with and converting hundreds of new subscribers.

We’re first going to show you a bird’s eye view of the whole welcome email sequence and will then go through each email in the sequence and break it down further.

Birds Eye View Of The Whole Welcome Email Sequence

birds eye view

Image source: Helpscout.net : https://www.helpscout.net/images/blog/2015/aug/autoresponder-sequence.png

The welcome series lasts 7 days, and the emails are spread throughout this period so as to not overwhelm or annoy the subscribers.

the welcome email

Image source: Helpscout.net – https://www.helpscout.net/images/blog/2015/aug/auto-responder-emails.png

With regards to the layout and design of the whole sequence, Helpscout opted for an uncluttered, well-structured and minimal layout. The colours are generally muted and there is heavy use of Helpscouts trademark yellow and blue throughout all the emails for brand consistency.

From a copywriting perspective, Helpscouts emails are written in an engaging, conversational, personable and friendly tone/style. Sentences are short and emotive and there are frequent uses of exclamation marks.

Detailed Breakdown Of The Emails In The Sequence

  1. The Welcome Email.

This email is short and sweet. The subject line reads “Welcome aboard! (please read)”. Helpscout found that adding the phrase “please read” in brackets improved open rates noticeably. Seems everyone needs a little nudge now and then.

Helpscout established two purposes for this first email “setting expectations and a friendly introduction”.

The company further kept the email light and friendly by opening with a joke and providing links to find further info instead of pasting walls of text directly into the email as no one wants that, especially not from a first email.

Helpscout went to great lengths in this first email to let the reader know that this is a two-way dialogue by providing subscribers with an invitation to talk to the Helpscout team in the email footer, as well as having face pictures of some of the Helpscout team and referring to the reader as “friend”.


– Take extra time to ensure the subject line of this first email grabs attention and generates clicks.

– Make sure you establish a clear purpose for the email.

the welcome email

Image source: helpscout.net – https://www.helpscout.net/images/blog/2015/aug/our-team.png

  1. Content Picks (Part 1)” Email.

The subject line for this email is “start here: our best writing on support, product, and more”. Helpscout considers this email the real start of their email series, which is indicated by the phrase “start here”.

This email is all about Helpscout providing some real value to their new subscribers by hand picking useful and popular content from across their long running blog on a number of topics that they feel their new readers would find interesting and helpful.

But Helpscout goes one step further in an effort to be more personable and add that human element. On the left-hand side of every content recommendation is a small round image of the Helpscout staff member that made the recommendation and below the recommendation is their name and job title.


– Do the hard work for your new subscribers by hand picking and curating the best content from either your blog or from around the web, this provides them with real value and they’ll thank you for it.

– Don’t be afraid to get personal and let the readers know which members of your team is providing the recommendations. That added human touch can go a long way and will separate you from the countless companies that don’t do this in their emails.

content picks part 1

Image source: helpscout.net: https://www.helpscout.net/images/blog/2015/aug/recommend-content.png

  1. “Curated Content – Part 2” Email.

Helpscouts subject line for this email is “5 more blog posts you don’t want to miss” which really plays on the almost instinctive FOMO (fear of missing out) feeling that a lot of people are susceptible to which makes this an irresistible subject line.

This email is a reaction to the previous email. The content in this email as well as who it goes out to will depend largely on which subscribers opened the previous email and which content in that previous, broader, email they most interacted with.

This email is all about Helpscout doubling down on what worked by sending this email only to those subscribers that engaged with the last one and presenting more of the content they reacted most positively to.

The footer of this email is also interesting. Helpscout ends with a “what’s next” teaser which gives the engaged subscribers a taste of what to expect in the next email and so increasing the chance that they will keep a look out for it and open it when it arrives.


– Use data from previous emails to better target later emails.

– It might be a good idea to write a short teaser paragraph at the footer of your emails to keep your most engaged subscribers excited about the next email in the chain. If you’re going to write one though, make sure the teaser gives them a good reason to read the next email.

curated content part 2

Image source: helpscout.net: https://www.helpscout.net/images/blog/2015/aug/curated-content.png

  1. The “Customer Success Stories” Email.

Helpscouts subject line for this fourth email in the sequence is “what successful companies know about customer support”. This is an enticing line as it plays on the reader’s natural curiosity to be “in the know”.

This email serves two purposes.

Firstly, it provides their most engaged subscribers with valuable information about what the most successful companies know that the readers can apply to their own businesses or lives.

Secondly, it indirectly provides testimonials of Helpscouts products by presenting examples of how successful companies have used them with the purpose of warming the subscribers up to the fifth and final email where they are offered a free trial.

This two-pronged approach of providing valuable, useful content and subtly weaving in testimonials at the same is a lot more persuasive then just presenting a wall of testimonials, as most companies do, which often comes across as too pushy/salesy and one sided and so does not have the desired effect generating conversions.

Helpscout ends this email by telling the subscriber that a “little surprise” is heading their way in the next email.

This phrase creates a small sense of mystery which has the effect of sparking intrigue in the reader’s mind and should ensure they keep a look out for the next email.

Who doesn’t love surprises?


  • Find ways of providing real value as well as your testimonials. Doing the latter without the former may result in your email coming across as too pushy and salesy.

customer success stories

Image source: helpscout.net: https://www.helpscout.net/images/blog/2015/aug/successful-companies.png

  1. The “Special Offer” Email.

The subject line of this final email in the sequence reads “Special offer: Try Help Scout free for 45-days!”. It’s clear and straight to the point. In Helpscouts words they decided to go for “clear over clever” for this final email title, likely to avoid any confusion or hesitation the subscriber may have.

Helpscout expressed how they were initially reluctant about “pitching” in their emails. However, they decided that by email 5 only the most engaged and interested subscribers would be opening the emails so they were the ones that are likely right and ready to try the product so wouldn’t likely find the pitch annoying or offensive.

And besides, as Helpscout state, they are in “the business of software, not newsletters”.

Eventually an offer had to be presented, but as Helpscout demonstrated, the important thing is to present the offer only to those that you are sure will be receptive to it and would want it.

So, in a way, the four emails leading up to this could be seen as not only building a meaningful relationship with subscribers and providing them with valuable, useful content but also as a four-stage process of elimination so when it comes to present the offer at the fifth stage only the most engaged and most suitable subscribers would be getting it.

However, as Helpscout explain, email should not be looked at short term. There will be many engaged, interested subscribers that open the fifth email and still not sign up. There are countless reasons for this and many of them would be out of Helpscouts control.

But when they are ready, which may even be 6 months or a year down the like, they are more likely to remember you and your software and come back to sign up as you spent the time providing the value and building the relationship.


  • With conversion based emails the key takeaway should be the overall strategy and philosophy that Helpscout adopted. Looking at which specific graphics and/or words they used is generally useless as your market, your product and almost everything else you are doing is different to theirs.It’s their approach that provides the valuable learning not their minute image and word choices. As it’s the approach that has been proven to work across various company sizes and industry sectors as it’s based on principles that are as old as humanity itself. Building relationships, building trust and providing people something that the need or want.

special offer

Image source: helpscout.net: https://www.helpscout.net/images/blog/2015/aug/45-day-trial-email.png



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