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Onboarding & Emails: How CakeHR Uses a 31 Day Sequence to Convert Free Trial Users into Engaged Customers

How to Convert Free Trial Users into Engaged Customers with Onboarding series

A comprehensive look into why onboarding is important, the role of emails in onboarding sequences and the deconstruction of the high converting CakeHR Free Trial registration follow-up.


Customer onboarding!

It’s a term most SaaS companies are familiar with.

They may even have a game plan around onboarding customers.

But there’s a lot of ambiguity and a distinct lack of consensus when it comes to two key questions:

  • When does onboarding start?
  • What is onboarding supposed to achieve?


Different Onboarding Perspectives:

Some brands believe that onboarding is a process that should focus on paid customers and work in concert with the efforts of the Customer Success Managers (CSMs) to increase the life time value (LTV) of clients.

Some feel that a welcome email for free trial users is enough onboarding to build transparent, rewarding relationships.

While other SaaS players carefully map possible touch points of interaction between company and lead to set-up a cadence of emails, calls and direct response marketing messages that convince potential customers of the value of their applications.

So which approach is more effective?

Based on the price of the application, the span of the buying cycle, the complexity of the user interface and the pain points the solution addresses, onboarding can be drawn out over a period of several months or be restricted to a couple of casual emails sent out after trial registration.


CakeHR and its Take on Onboarding:

CakeHR is a human resource management suite that takes the hassle and overwhelm out of HR for SMBs. It is rapidly becoming the most popular choice for businesses that wish to scale and grow through advanced yet concise reporting, HR access on the go, efficient employee onboarding and a robust 360-degree feedback process.

So when it comes to onboarding its own potential customers, CakeHR employs the most effective guidelines:

  • Onboarding starts the minute the prospect engages with the brand for the first time.
  • Either by reading an article on the blog or by signing up for the 30-day free trial.


This supposition is important because given the level of competition in the HR solutions market, underwhelming a prospect or inadvertently providing a poor brand experience is akin to losing an opportunity forever. This is the reason why, everything from website Calls-to-Action to the actual tool tips within the application are optimized to serve as onboarding touch points.


The purpose of onboarding is to:

  • Help the user realize the fact that CakeHR solves their pressing problems
  • Explain how the tool works in the simplest terms possible
  • Help potential customers secure their first “win” with the application


Onboarding is non-negotiable.

It reduces churn and even a 1% difference in this number can have a 12% impact on the valuation of the company in 5 years.

40% to 60% of free trial users log into the application once, never to return again. Robust onboarding that holds their hand and guides them through the best practices of utilizing the tool can also improve the return-to-app rate of prospects.

And it has been found that free-trial users who complete their onboarding tasks within 24 hours of registration have an 80% chance of converting into paid customers.


Onboarding & Emails:

Emails are ubiquitous.

On one hand they land in the inbox or the private space of prospects and are harder to ignore than Facebook posts or Tweets. On the other they are nowhere near as obtrusive or insistent as a phone call and respect the availability of the receiver.

All channels of communication have their place in the marketing mix.

But the need for personalized information during onboarding is best served by a sequence of emails tailored to respond to prospect behavior and preferences.

All in all since email is already 40 times more effective at acquiring new customers than social media, CakeHR uses its potency to drive the bulk of its onboarding campaign.



The Exact 31 Day Free Trial Onboarding Sequence for CakeHR:

Day 0:

Email #1: Welcome Email

Sent: Immediately after free trial registration is confirmed


This email looks to generate enthusiasm in users. It congratulates them on taking the wise decision to test the CakeHR application suite and sets the right expectations for the coming 30 days.

CakeHR nurtures free trial prospects through a balanced mix of professional tips and action reminders.

The email establishes transparency by letting leads know that they will receive “bite sized tips” to help resolve their Human Resource related challenges.

Call to Action:

The clear CTA is to log into the CakeHR application and explore the functionalities.

Image of welcome email.


Day 0:

Email #2: Highlighting Biggest Pain Point

Sent: A few hours after Email #1


This email defines the rhythm of the application’s usefulness which continues to build over the next 30 days.

It starts off ambitious by positioning CakeHR as the solution to the biggest hassle most HR employees and managers face – overwhelm resulting from a deluge of requests and a fire hose of information.

The email talks about the fact that:

  • CakeHR is essentially self-service and empowers employees to manage aspects of their work, like time-off requests on their own without needing to bother their supervisors.
  • CakeHR brings order to the chaos of employee availability with a central calendar capable of tracking policies and resource availability.
  • CakeHR can run advanced and ad-hoc reports which make sense of employee data, reciting the stories inherent in labor behavior patterns.


Call to Action:

The clear CTA is to log into the CakeHR application and explore the functionalities.

Getting started email example


Day 2:

Email #3: Reminder to add days-off

Sent: Only to those who haven’t added time-off to their calendar yet


This email is a conditional message sent to prospects who do not take the validating action of adding “time-off” to the calendar.

Since this task is simple but it mitigates a primary HR pain-point of leave tracking and request overwhelm, it is one of the two behaviors identified as early wins for free trial registrants.

The email reiterates the convenience of automating the process of granting and managing leaves.

And it ends with the offer of populating the trial account with the company data.

The main aim here is to remove all possible resistance from the path of initiating the action. Accounts that are rich with information are harder to abandon when the free trial is up.

Call to Action:

The call-to-action is to schedule a slot for a quick demonstration of CakeHR over which the lead can hopefully acquire the confidence to start using the account.

Call to action email for demo example


Day 2:

Email #4: Reminder to add employee details

Sent: Only to those who haven’t added employee details yet


Another low barrier action that invests a free trial registrant in the account is the inclusion of employee details.

Through this email the account executive offers to populate the application with relevant employee data and when sends a primed spreadsheet over to make the process easy.

Everything about the message looks to build credibility and provides the impression that CakeHR is always there to support customers.

Call to Action:

The clear CTA is to log into the CakeHR application and explore the functionalities.

Reminder to add employee details example


Day 3:

Email #5: Introduction to document management and directories


This email continues with the theme of easy information organization.

It encourages the registrant to enjoy a sense of freedom from “dusty filing cabinets” and in essence most tedious and physical data repositories by easily uploading files and creating a centralized log of employee details.

Since file sharing and collaboration are important to Human Resource managers, the email also touches on this feature of CakeHR.

Call to Action:

The clear CTA is to log into the CakeHR application and explore the functionalities.

Introduction to document management and directories email example


Day 4:

Email #6: Introduction to the CakeHR mobile app


The email is designed to drive CakeHR mobile application downloads.

It weaves a story around the popular trend of on-the-go managers and Bring Your Own Device (BYOD) to convey the message that CakeHR is just as effective out of the office as it is inside the cubicle.

Leads who also download the mobile app are considerably less likely to abandon their free trial account since CakeHR is now on several devices.

Call to Action:

The CTA here is to download and install the Android or the iOS versions of the mobile application.

Introduction to the CakeHR mobile app email example


Day 6:

Email #7: A demo invitation

Sent: Only to those who haven’t logged in since the start of the free trial


Demos always engage leads because they put the potential customer in touch with human executives and they also provide a clean overview of how the application can solve business specific problems.

The aim of this email is to get the registrant to schedule a quick demo with the promise that the time spent will result in more strategic HR wins for the company.

Call to Action:

The CTA reflects the purpose of the message with an invitation to schedule a free demo.


Day 8:

Email #8: Introduction to teams and organizational charts


A generic database of employees isn’t the right way to maximize talent output. Most companies lack structure when it comes to labor and stakeholders are unsure of who does what.

This email agitates the pain point of hierarchy confusion and introduces popular CakeHR aspects of teams and the visual organizational chart as possible solutions.

Through the use of teams and stylized organizational charts free trial registrants can dedicate managers, give context to various roles within the enterprise and maximize efficiency.

Leaving leads to sink or swim within the app is not the trademark of a well thought out onboarding sequence. To this effect the email is another bid to map real world HR problems to features offered in the CakeHR suite.

Call to Action:

The clear CTA is to log into the CakeHR application and explore the functionalities.


Day 9:

Email #9: Reminder to add teams

Sent: Only to those who haven’t added teams to their account yet


A high value action that cements the possibility of upgrade is assigning managers to workers and creating teams within the application.

When leads execute this onboarding prompt, they are on their way to the important milestone of making the application relevant to focused groups of employees.

Keeping this in mind, the email is a gentle nudge to set-up teams with the convenient offer of CakeHR account executive assistance to complete the task.

Call to Action:

The CTA for this email is to add in the teams. Apart from this direct request, the email also provides a link to a support document that elaborates on the process to do so.


Day 10:

Email #10: Invitation to join a 1-2-1 meeting


HR managers are humans. And this email is geared to flip their prestige and curiosity persuasion switches.

The message captures the attention of the lead with the mention of “exclusive tips and tricks” that can skyrocket efficiency of the workforce.

It builds on this foundation by also promising to position the lead as the “best HR manager” in the company.

This combination is in most cases extremely powerful.

Call to Action:

The clear CTA for this email is a call to book the 1-2-1 session.


Day 11:

Email #11: Reminder to download the CakeHR mobile app

Sent: Only to those who haven’t downloaded mobile app yet


This email simply re-introduces the CakeHR mobile app which comes with the lucrative benefit of giving employees the flexibility to check balances and request time-off on the go.

Call to Action:

The CTA prompts the lead to download the Android or iOS version of the mobile app.


Day 12:

Email #12: Introduction to CakeHR integrations


A sound onboarding sequence strives to make the SaaS application indispensable to the lead.

A great way to do this is to integrate the solution with platforms that are already a part and parcel of the registrant’s professional life.

The email drives home the versatility of CakeHR by prompting the prospect to synchronize it with oft-used solutions like Slack. This is not only genuinely convenient; it also increases the likelihood of an upgrade at the end of the free trial.

Call to Action:

There are three CTAs associated with the email.

One is a call to synchronize CakeHR with Slack. One is a call to explore Google Apps that are a good fit with the suite. And one is a call to link the application calendar with iCal or Google.


Day 13:

Email #13: Introduction to Audit Logs and Permissions


The email talks about a very relevant HR pain point – unauthorized alterations.

Managers are often at a loss where changes made to spreadsheets are concerned. It is impossible to trace these back to employees and dozens of man-hours are wasted sorting time-off requests and pondering, “Who tweaked what?”

CakeHR’s log audit and permission customization translate into tight control over the ability of employees and managers to view and alter information or requests.

The general tone of the message is one of empowerment. The issue of unauthorized alterations brings with it a sense of helplessness and CakeHR is the user-friendly antidote.

Call to Action:

The clear CTA is to log into the CakeHR application and explore the functionalities.


Day 14:

Email #14: A friendly check-in


The email reminds the prospect that two weeks of the free trial are up and encourages the lead to start a conversation with the account executive.

It is a well-known fact that responses during trial auger well for the possibility of upgrade because a reply is a form of micro-commitment.

This message tries to elicit a response and drive engagement.

Call to Action:

The CTA is for the lead to hit “reply” and ask questions.


Day 16:

Email #15: Security assurance


Each instance of data breach can cost a business up to $158.

Most companies are paranoid about data security and they have good reason to worry.

This email attempts to remove what might be one of the most significant blocks keeping leads from upgrading to a paid account.

It reassures them of the safety of their sensitive employee and balance information by listing front end and back end protection provisions. It also links leads to CakeHR’s privacy policy to further cultivate trust.

Call to Action:

The clear CTA is to log into the CakeHR application and explore the functionalities.


Day 18:

Email #16: Crunching numbers


By the 18th day of the free trial leads reach a decision about the suitability of CakeHR as their human resource management platform.

Directing them to features and functionalities is no longer the way to a paid account.

This is why the email shifts gears and talks about the possible financial investment in the platform. Since the SaaS subscription model is scalable, the tagline of “pay as you grow” has been chosen to convey the advantages.

The price per employee added to the system is also pulled into the conversation to give the HR manager a chance to crunch ROI numbers with those who will ultimately pay for the application.

Call to Action:

The CTA extends the invitation to jump on a call and ask questions about payment options and the fine print.

This session if booked gives the prospect a chance to collect information that can convince company stakeholders of the benefits of going with CakeHR.


Day 25:

Email #17: Direct CTA to upgrade


This email is succinct and guides the lead to the billing section of the app for a possible upgrade.

It wraps up the conversation with a reminder of the savings and the efficiency boost that come with the regular use of a CakeHR account.

Call to Action:

The CTA is for the lead to head to the billing section and add the payment details.


Day 31:

Email #18: Last attempt to win over the lead


This email is scheduled for the 31st day and goes to the leads who don’t upgrade during free trial.

It stimulates FOMO by touching on the fact that the prospect will eventually lose access to the data in the trial account if a subscription isn’t purchased.

The email also talks about the possibility of a free trial extension through a call with the account executive.

Call to Action:

The first CTA is for the lead to purchase a subscription plan. And the second call-to-action encourages the prospect to schedule a session to discuss a free trial extension.


The 18 email, 31 day sequence onboards prospects and removes the barriers that might keep them from converting into paid customers.

The emails, without exception:

  • Come with a featured image for visual stimulation
  • Are short, personable and to the point
  • Focus on the lead with multiple instances of the use of “You”
  • Tie real HR pain points to CakeHR features


Author bio
Norberts Erts is co-founder at CakeHR. Protagonist of marketing, avid growth-hacker, tech junkie and HR generalist. Keeping a sharp eye on international news, politics, business, finance, science, technology and the connections between them.

Onboarding & Emails: How CakeHR Uses a 31 Day Sequence to Convert Free Trial Users into Engaged Customers
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