The Ultimate Compilation of Customer Acquisition Strategies for Your Self-serve Business

You are a self-serve business model. Probably even a hybrid of a self-serve and a sales-driven model. Your business model is a conscious decision, birthed from the nature of your product, your approach to the sales model, or even your goal of scale.

While the self-serve business model by itself is a fuel for acquiring more customers, one of your top problems will continue to be acquisition and conversion at scale — with minimal human intervention and maximum automation.

For your business, a typical acquisition pattern may look like this: Prospect discovers your top of the funnel blog post on Google, an ad, or a mention in a publication. Prospect, then, visits your pricing page. Prospect signs up for a free trial.

The acquisition pattern for your business is driven by people (teams), processes, and products. Your sales and marketing teams will actively drive people into the website and the product, and convince them to try out your product or service.

But there's more. It starts from the payments page — automating collection of customer and payment information and creating a record. And it ends with ensuring every last information is collected, your prospect has converted into a customer, you have closed the loop. Until renewal is in the vicinity.

There's a lot in between the two details.

For instance, a user dropped off from your checkout page. You will want to target this set of abandoned users with an "End of Year" discount campaign. You'll want them to sign up for an extended trial for them to get a feeler of your product. One of the users has signed up with your offers, but wants to pay via PayPal. Once inside your product, the user now wants to upgrade to a higher plan all by herself.

And with all your offerings, you want to be able to track usage, and assimilate learnings of which channel has performed better.

The challenge is, you will have to write more code in your existing codebase to tie the coupons back to your subscriptions.

The spaghetti gets messier with time. But what if you have a tool that has these capabilities inherently? And this is where your billing system will help.

We have six avenues for experimenting with customer acquisition, with stories from

What does your self-serve journey look like? Let us know by writing to We'd be more than excited to accompany you on your growth journey.

What's in your pricing?

Iterate your pricing and experiment with different pricing models

The key to pricing is to always keep testing.

Pricing has always been a tricky affair. Price too high, you lose customers. Price too low, you lose value. Finding the sweet spot has been one of the oft discussed topics in the realm of SaaS. And every pricing expert will recommend that you need to keep testing and iterating. Just like we did.

Because, getting to the product-market fit is a continuous process. You'll always end up identifying a new persona, a niche market, or a different vertical you're catering to.

And you'll almost always end up finding yourself evaluating your current pricing.

Do you iterate on pricing such that any change to the product reflected in the value and pricing, like Shopify? Or do you revise the pricing understanding the customer segment, like Zendesk? Or do you tailor your pricing according to the core differentiating features, like Statuspage?

Do you grandfather your existing customers? What impact will that have on your new sales and expansion revenue? Do you localize your pricing to suit the current geography?

In any of these cases, your billing system will help close the loop by:

  • Offering flexibility in pricing models — freemium (a portmanteau of free + premium), flat fee, usage based pricing, volume pricing, tiered pricing...
  • Grandfathering the customers you want so your pricing changes only apply to your new users
  • Offering flexible payment options to customers in transition (with segmented plans, advance invoices, and discount options)
  • Offering custom pricing — potentially during an upgrade or in a hybrid sales model
  • Converting your pricing in the native currency

And in all of this your billing system should back you up — to allow you to make these pricing changes, without an extra line of code, so your customers find no discrepancy in your pricing. Should your customer upgrade to a higher paying plan mid-cycle, your billing system should prorate the amount.

GetAccept, An AI-based eSignature & deal management platform, adopted a hybrid approach when it came to sales — an outbound sales-driven model as well as a self-serve sign-up model. As they scaled, their customer acquisition strategy pursued different use-cases and required a platform that allowed for pricing experiments including support for tiered as well as dynamic pricing for enterprise sales. And for mid-cycle expansions, this needed to be done on a pro-rata basis.

Iterating on pricing and custom pricing, among other experiments contributed to GetAccept's revenue growing 4X at the time — businesses should take a leaf out of GetAccept's growth storybook.

Here's how Doodle Scaled Globally with Localized & Tiered Pricing Model

Switzerland-based scheduling app, Doodle, is a freemium tool — where users sign up for a forever-free plan, and you need to upgrade to a paid plan to benefit from additional capabilities.

"Most of our customers start by using the freemium product. They come to Doodle, create poll (which means they're trying to find a time to meet). These people come again for other meetings. If they have organized enough meetings, we run a campaign to prompt you to consider the premium product, or we suggest that it'd be a good idea to have all these additional features. And you'll use one of the teasers we have in the product and go through the purchasing flow. Not a very sales-heavy process. Only for big companies with a lot of users using the product do sales get involved,"
Cliff des Ligneris, Product Manager at Doodle

Doodle saw that the value lay in adding more users to an account i.e. offering paid plans based on the number of users/members in a team. And at prospects who are at scale, it's highly likely that they'll have different team sizes willing to use the product.

Doodle wanted to capitalize on that and offer their product across multiple currencies with individual prices and different tiers. Today, they offer Tiered Pricing — instead of offering a single option of pricing and bucketing them into a "Buy" or "No Buy" situation. As a result Doodle's prospects are able to select the plan that resonates with them the most, and aligns with what they value the most.

Doodle's free plan supports ads. Along with this, Doodle also offers two ad-free, paid plans using Chargebee's tiered pricing - a 'Private' plan at €43 per year for a single user, and a 'Business' plan at a base price of €59 per year depending on the number of premium users signing up for the product. Typically, this works for businesses with professional teams of different sizes.

For further reading:

Here's more on how you can experiment with pricing strategies.
Here's more on the good, the bad, and the in-between of Freemium model.
Here's more on what you can learn from AWS on the freemium model and how you can apply it to your business.
Here's an absolute complete Pricing and Trial Playbook [Must Read]

How do I sign up?

Spend time on the checkout page for better conversions

A conversation with one of our (Customers/prospects) opened up a new understanding of how businesses perceive checkout. A quote directly from the Co-Founder:

"One of the troubles with (the payment page) is we want to be AB testing our checkout page itself. This one has like 6 years of testing. It might not look like it's had a lot of testing but it's constantly tested. We've kind of come to this point where it converts particularly well with our customers. We'd rather not abandon that given the type of competition that we have."
"Basically there is like 0% chance of us using the hosted option. Even if we were to abandon all the learnings we've had over the last 6 years, we'd still want to be AB testing the most important page on our site like this is the page where the people finally drop their credit card information. And we want to make sure everything is consistent, feels right, like we have the preview of their document on the right hand side, we have like the right language which every part of it has been tested to..."

For a critical page such as the payments page, it then becomes important to support the kind of flexibility the businesses seek.

Your pricing page is the ultimate courting dance of the user with your product — "Do I? Don't I?" — this is where your users convert into customers in your acquisition funnel.

Optimizing for your checkout experience means ensuring your checkout and payment pages are designed in a way that pushes for better conversions. These areas for optimization should include:

  • Stating clear CTAs so your prospect moves down the funnel
  • Allowing for flexibility in payment options, with additional payment methods
  • Customizing your checkout — to display the checkout in local languages, or display pricing breakdown without hidden charges
  • Adding or limiting information fields — so you can collect more information about your customers, or avoid information overload
  • A/B testing your checkout — so you know which design on your payments page gives the best outcome

Here's how Freedom Bolstered their Conversions by 33% with this Hack on their Checkout:

Freedom is a North Carolina-based productivity tool that blocks sites and apps to avoid distraction and do deep work. Headed by Fred Stutzman and his team, it is used by more than 75000 users worldwide.

As a B2C product, Freedom scaled fast. But their simple integration with Stripe did not support the scale in a way that they'd have liked. Rather, it was being an impediment to their growth.

One of their critical problems was the ability to support multiple payment methods, something Stripe did not offer at that time. Acquisition ended up bleeding.

Freedom solved for this in 2 simple ways —

  • Allowing for additional payment methods including PayPal and Amazon apart from credit cards
  • Offering a limited 7-days trial period and allowing their customers to manage their own subscriptions using the self-serve portal

Freedom switched their checkout process with Chargebee's PCI compliant hosted pages. This boosted their conversions by 33% once they optimized their acquisition flow.

For further reading:

Here's more on how you can improve acquisitions and conversions on Checkout.
Here's more on how you can use Chargebee Moments to run experiments on your Checkout.

It's a trying time.

Trial Experiments that push for improved acquisitions and better conversions

For Doodle, the freemium model worked. One of the reasons that made it work for them was the value metric they anchored their pricing on i.e. number of users in a team. Had this metric been anything else, it'd have been a disaster, like bringing in the wrong set of users.

This happened with Chargebee's freemium based on the number of invoices before our (now) Launch Plan — when we offered 10 invoices for free and on the 11th invoice, the user upgrades to a paid plan. This ended up bringing in consultancies and agencies that did not have a huge customer portfolio.

But freemium isn't every business's cup of tea. For most B2B businesses, freemium users take about 5 - 6 months to convert into paying customers on an average. Yes, it helps you acquire more customers. But if you're someone who says, "I got my users, but they aren't really paying...", it's probably time to revisit the strategy.

Enter free trials...

Free trial has become the de-facto for SaaS businesses, typically under the SMB segment. Free trial is largely recommended as a must, if your product is competitively priced. You'd want your prospect to try before they buy, of course.

Free trials also comes with its share of options, and like pricing, it becomes pertinent to experiment with trial patterns. Some of those experiments should be around

  • Trial lengths — businesses with annual plans have discovered that longer trials convert better than shorter ones.
  • Ability to extend trials
  • Provide upgrades to a paid plan mid-trial
  • Accept users to sign up for trial without card details
  • Allow for paid trials

The more important thing to take care of here is to take into account, context. Is your product designed to demonstrate value in the limited trial? What kind of communications or nudges do you plan to push during trial? How will your product demonstrate its value? How long will it take for a customer to realize it? And how will you shape your freemium strategy around this in such a way that the moment the customer understands the value, your product nudges them to move up to a paid plan?

Here's how Riddle Ditched Freemium for a Free Trial, and Boosted New Sales by 34%

Germany-based marketing and lead-gen platform, Riddle's story was similar. Riddle's freemium plan worked beautifully as an acquisition channel, bringing in thousands of subscribers. The problem was with converting them into paying customers.

"We also realized pretty soon that offering a free plan with hopes of converting users to a paid subscription is not a good idea. The users on the free plan ended up being responsible for a large portion of our expenses but never had any intention to ever upgrade,"
Boris Pfiefer, Founder, Riddle.

Riddle's free-to-paid conversion was suffering.

They solved the problem in two ways.

  • Deserting the freemium strategy to force customers to upgrade to a paying plan after a limited 2-weeks trial.
  • Combining that with allowing users to checkout without sharing their card details.
"When removing the free plan and replacing it with a no credit card needed, no limits free 2 week trial, we saw a very large increase in subscription sales,"
adds Boris

Riddle's new approach, in conjunction with offering their users discount codes to facilitate better acquisition and conversion resulted in 34% increase in new user subscriptions.

For further reading:

Here's more on how you how you should perceive SaaS trials with and without credit card.
Here's more on how Chargebee increased Trial-to-Paid Conversions by 7% By Optimizing For Common Conversion Activities

What's my incentive?

Discount Campaigns to nudge prospects down the acquisition funnel

Here's the thing about discount campaigns — there's more than one use of your coupons. Your discounts will be used to reheat cold prospects. You will use them to nudge a trial user into a paying customer. You will also run targeted discount campaigns to those who dropped off on your checkout page. And then there are the festivals and seasons where discounts are always welcomed by customers.

Here's another thing about discount campaigns — it will become incredibly messy if you were to run your coupon campaigns using a coupon management system. Or any other system that has a rudimentary coupon management functionality. For every customer acquired through a coupon, a corresponding subscription needs to be created, with the coupon details generated in their invoice. The coupon you issued needs to be trackable, and this information being reflected in the reports.

While you are busy motivating visitors to sign up for your product with promotions, you will end up demotivating yourself with the spaghetti code after spaghetti code.

... we wanted to be able to try [special discounts and trackable coupons] and every time we wanted to do any such thing using Stripe we needed to go through... it was a lot of spaghetti code we had to write to do anything
Keerthik Omanakuttan, Co-Founder, BitGym

Coupons and promotions boost conversions by providing the kind of incentive your users need to sign up. And your billing system helps close the loop on them, allowing you to segment the customers you want to send the coupon to, track how many people use it, change the subscriptions of people who do, alter the charge on the invoice, and factor the change into reports.

That thanksgiving coupon will seem a lot less debilitating when you have the support of a billing behind you.

Here's how BitGym Upped their New Sales with Seasonal Discounts and Payment Options:

BitGym is a US-based cardio app for Android, iOS, and Kindle, which loads up a video of different beautiful locations worldwide. From a Kickstarter campaign to one-time in-app purchases, to a Netflix-inspired subscription business model, BitGym has seen it all.

BitGym doesn't collect the users' details right from the pricing page. Instead, they let you sign up for the product, collect information that will help tailor experience later.

Being a lean team of less than 10 members, BitGym started looking at expanding their marketing options, well, without a grand marketing team. They wanted to funnel people into the app directly from their website, but more meaningfully. Here's an example: for a fitness app, they observed that they would see a spike in their subscriptions during the bloom season.

In order to capitalize on this seasonal behaviour and expand their acquisition channels, BitGym would roll out special discounts and trackable coupons, with a one-time payment link. This incentivized more users to sign up to BitGym.

This, along with offering additional payment options including Credit Card (via Stripe), Amazon payments, and PayPal, increased their monthly paying customers by 2x at that time.

"We had growth that was bigger than our previous year in the year that we switched to Chargebee. We ascribe at least some of that to the fact that we made it very clear to our customers that we can now use all these other payment methods and we would go back and email users who had contacted us previously asking if they could and told them that yes, this is now an available option,"
Keerthik Omanakuttan, Co-founder of BitGym.

For further reading:

Here's more on how to use SaaS pricing discounts to grow revenue by Lincoln Murphy

I forgot your product exists...

Email Notifications for effective and contextual follow ups

Think of the last time you booked your flight tickets, and you received the order confirmation. How many times did you open this email? Now remember the last time you opened a newsletter email that you don't remember signing up to. Chances are that the former email required you to engage with it far more than the latter.

Transactional emails have 8x more opens and clicks than any other type of email, and can generate 6x more revenue. As someone who holds the keys to data from every checkout and every sale, it'll be worthwhile to use this information to initiate potential conversations with prospects — the worst that could happen is, they are reminded of your product with a minimum amount of engagement. And the best that could happen is they become customers.

Transactional emails such as an on boarding email present an opportunity to get customers move from a trial to a paid plan — you could start conversations, personalize your product recommendations, or even offer discounts. They also help in recovering potentially lost revenue, should a transaction fail.

Well, of course you could use an email marketing platform to run these campaigns. But here's the challenge. What you would lack with the emails from your marketing platform is context.

For instance, you'd like to automate a timed-discount campaign plus a trial extension email campaign to a segment of subscribers whose trial period is close to expiry. Your billing system will present this context far quicker and easier for you to run your campaign. Or, you want to email subscribers whose cards have expired, requesting them to update their card details to avoid involuntary churn.

Your billing system will be able to provide that context — it allows you to segment and automate transactional emails, and any subsequent outcome will be tied back to the subscription status and reports. Here's an outline on how you could leverage transactional emails to improve acquisitions and conversions.

  • Automate a welcome email on sign-up. Research suggests that you have a 'window of 90 minutes [after trial sign-up] before a lead goes cold'
  • Extend the trial for users that are engaged but reluctant to sign-up, and nurture them a bit more in the process.
  • Make sure that technical difficulties don't result in failed payments and involuntary churn with pre-dunning.
  • Use billing information to make your acquisition funnel healthier

Your billing system should be equipped for a complex problem like acquisition — so you can run experiments with direct impact to the visitor-to-lead and lead-to-customer conversions.

Here's how Whiteboard CRM Reduced Churn by Almost 100% and Increased MRR by 35%

Whiteboard is a US-based mortgage-CRM that helps Loan Officers and their teams systematize the mortgage process and cultivate relationships with their partners in the real estate space.

For Whiteboard, the biggest challenge while using PayPal and then Braintree for automating their recurring billing was lack of a solid automation to recover revenue from payment failures and send email communications for follow-ups.

"A member of the team would spend hours every week chasing customers. And we were inconsistent on policies surrounding deactivation and cancellation,"
Ben Laughter, VP Customer Success and Operations at Whiteboard.

This lack of follow-ups had a direct impact on their churn and MRR. Once they moved to a full fledged billing system, they were able to set up automated emails for every subscription event, including when collecting failed payments.

"I love that we have automated emails going out for all manner of events. Successful renewal, upcoming renewal, quotes, and subscription changes come to mind. Chargebee makes it easy to manage what those emails say and how they're formatted,"
adds Ben

Standardizing and automating the vast majority of their follow-up processes when payments did not go through, increased their MRR by 35% and brought down their churn by nearly 100%.

For further reading:

Here's more on how you can ace transactional emails
Here's Campaign Monitor's complete guide to optimizing transactional emails.

Automate. Rinse. Repeat.

Building an integration ecosystem that just works.

Building a self-serve SaaS product translates to more power in the hands of your customer. Of course, it doesn't mean that there is no human touch when your customer uses your product. But, for a self-serve business to be able to operate at scale, it's important to be able to build as many automations as possible.

Automations are powerful, because they let you invest in ways to be more human with your product. Strange, right?

For instance, if you have a customer who has signed up with your product, and you have built an integration with Slack, that notifies you of this, you immediately drop a "welcome onboard" note to your customer, and send additional onboarding materials and training videos, on the go.

Or here's another instance. Say you have a prospect who's on trial which is coming to an end in two days. An integration with Intercom will let you push for better activations with a more contextual question and support such as "Hey, I see your trial is ended. Were you able to play around with our reports? Here's a tip on how you can reduce your churn..." can go a long way.

Or here's one more instance. You are a B2C SaaS with high volume and low ARPU. A solid integration with Xero helps you reconcile thousands of payments in a single go, without you having to shuttle between multiple CSVs and imports and exports. And your finance team can focus on drawing the bigger picture, perhaps identifying a better acquisition channel with low investment and high RoI.

All of these automations paired with the ability to detect opportunities serve as a good fodder to find potential high value customers who are more likely to benefit from a more personal touch.

How Proxyclick uses Intercom to nudge Trial users in Chargebee into activation...

Proxyclick, a Brussels-based visitor management solution, started scaling globally with a mix of SMBs and Enterprises among its audience. Pricing was never an issue — they would offer a fixed pricing on the face of it, but also allowed room for negotiation with dynamic pricing.

Proxyclick put in a lot of effort to onboard their customers into the product. Introducing a human element wherever possible was one of their key requirements. With a limited 15-days trial period, they wanted to identify every avenue where they could guide their users on to the next stage of the acquisition funnel.

Proxyclick's marketing would track the journey of their trial users in the product. They designed outreach and onboarding campaigns around this journey, moving their prospects into the nurturing bucket.

How did they do it? Chargebee's integration with Intercom using webhooks gave them visibility into their prospects' trial status, and once they were close to ending their free trial, they'd push relevant and contextual messaging, offering guides and tips, that led to better conversion.