While finding product-market fit for Palabra, our marketing strategy was exclusively organic and our first sales came from 1-1 conversations with potential users. After a month of difficult conversations and failed demos, I learned a very new and innovative approach to direct sales: actually listening to what people are saying. In this post I’ll share my experience and some tips to listen to users, in the hopes of saving founders & early startup teams some time and energy.

What we mean by direct sales

As the name suggest, direct sales means you talk directly to your prospect and try to sell them your solution via a 1-1 conversation. This conversation usually starts by reaching the prospect you think your product would work for, and sharing why you think your solution would be good for them.

Taking a direct approach is more common for B2B businesses, because the decision to purchase is strategical and the price is higher, which means you get a bigger return for each user you convert. But I think it’s a good strategy to follow for any early stage SaaS, because it’s an easy and direct way of learning about your users and implementing solutions that work for them.

The biggest challenges to direct sales is finding the right prospects and knowing how to show them value as quickly as possible. With direct conversations you’ll probably get a higher conversion rate than self-served sales, but at a much slower rate.

Why direct sales in a SaaS startup?

When we launched Palabra we had no audience and not enough user data to understand who we should be targeting or how to convert them into paying users. We had two possible paths to follow:

  1. Awareness-first: Experimenting with low-budget ads or organic strategies in different channels, with different messages to see which stick better. This approach is the startup playbook, feeding the top of the funnel with as many prospects as possible assuming most of them will not end up buying, and learn how to convert them better later on.
  2. Conversion-first: Spending almost no time to feed the top of the funnel (keep a low stream of leads and prospects) but improving that funnel to have better conversions. Leads would be scarce, but we’d learn how to qualify them and provide value so they are willing to buy and stay around.

The first path was the riskier for us. First, because we had little experience with paid acquisition, and wouldn’t know if our misses would be due to lack of experience or just wrong channels.

Second, we wanted to engage in deep conversations with users as soon as possible. We didn’t really care about general trends, we wanted to actually understand what people were struggling with in email automation, and where to take our product so that it worked for them. That’s why we decided to take the second path.

Our initial strategy was to ask a bunch of questions about people’s current email automation strategies and try to turn the initial conversation into a sales pitch. We’d learn fast and get a few sales in the meantime.

Sounds easy, right? Well, it was not.

What a failed sales conversation looks like

After my first couple of calls I knew I was doing something wrong, but didn’t know what it was. Sign ups were rarely because of my “sales” 1-1s, and every conversation left me with a sour feeling.

What usually happened was that I got to a call, asked the person a couple of questions about their strategies, and at some point I’d get nervous and start talking a lot. People are usually nice and would listen to what I had to say, but I could feel they weren’t really interested, and felt like I was wasting time.

So what was I doing wrong?

After talking with my co-founder and a couple of friends in the SaaS industry, I found that I wasn’t really paying attention to what prospects were saying. My team would ask questions about our prospects that I didn’t know how to answer.

That meant I wasn’t really selling, but I also wasn’t learning about our users. I found I had to learn how to listen first, and sell later.

How to talk less and sell more

Listening to prospects is not at easy as it sounds when you are worried about selling them your solution. Specially if you’re in early stage and don’t have much experience selling software, it’ll be hard to keep a clear mind and letting the user take the conversation where they want to.

But here’s the thing: selling isn’t about convincing people to try your product, it’s about identifying how your product can solve a problem for them.

In a direct sales conversation, you should have two take outs:

  1. Identifying if the person you’re talking to has a problem you could solve (the more details the better)
  2. Communicating clearly how your product is a solution to their problem.

If you fail at #1, you’ll end up trying to convince people who don’t actually have a problem you could help them with. Those are not your users, and there’s nothing you can do today to make their life easier. Even if you somehow convince them to sign up, they’ll probably cancel their subscription, making your churn go up.

Failing at #2 is usually connected to #1, because the only way of communicating a solution clearly is to understand the problem perfectly. You have to listen really carefully to understand what those problems are.

Most of your conversations with prospects should be about #1. Make a lot of questions. Listen closely and follow up on what isn’t clear. Make the other person feel listened to. Worst case scenario, you end up with valuable insights about what problems people have. As an early stage startup, this information is crucial to find product-market fit.

Here are some lessons I learned while taking a direct sales approach to SaaS. Most of them came from reading The Mom Test, talking to awesome people and experimenting on my own.

3 direct sales tips to listen to your users

Writing down what you want to get from the conversation

This list should be really short. My initial conversation guide had 15+ questions to get to understand the problem, and then a short demo. It worked kinda fine, but I usually got lost by question 5, and then started thinking about what to ask next instead of listening to the answer.

The Mom Test suggests you should “prepare your list of 3”. Three things you want to get from each conversation, depending on who you’ll be talking to. And that was magic.

In early Palabra demos, when I asked to have a quick chat to someone in a startup, I usually had three different scenarios:

I prepared three different notes to look at before each conversation, one for each “buyer” persona, and wrote down my list of three.

I started asking questions that came to mind from listening to what people were saying, and spend almost no time looking at my notes. If I ever felt I was starting to get lost, I just glanced to my list of three for that particular person to check if I was missing something. Freedom.

Having a structured set of questions

This advice came from a great friend and the best UX designer I’ve met. She knows all about user interviews, and since I was also trying to learn from our prospects, I knew it would help. Her advice was to divide my questions into chunks or topics I wanted to know about.

Having differentiated topics gives you flexibility to follow the conversation and not worry about what to ask after each answer. If you ask a question from the first topic and your user’s answer goes to a slightly different topic, you can go to that part of your guide and then come back after that’s done.

As an example, this was the structure I ended up using for each guide:

What usually happened is that my email questions got answers related to tools. So I just moved over to the “tools” set of questions and then looked to see if I was missing something important at the end.

A smart move was to leave questions about pains for last. By then I usually had enough information about their problem and could offer a clear solution with Palabra.

If we had a solution, I’d briefly tell people why I thought this would work, and offered to show them in a demo. By focusing on their specific solution in the demo, I only showed one feature and not the whole product, which was a much better use of everyone’s time.

Doing some background research – but still ask people

You can’t go into a sales pitch without knowing who you’re talking to. For B2B sales you need to know about the company and the person you’re actually going to talk to. The key here is to use that information wisely.

I used to start conversations on what I’d learned from their landing page, to let people know I had done my homework. But his was actually making me start with the wrong foot -by talking too much.

Asking about their company and what they do there gives you inside information you wouldn’t get from LinkedIn or a landing page. And it also helps break the ice, since it’s an easy answer for anyone.

My solution was full transparency. I started each conversation by saying I had done a bit of research about them but still wanted to hear from themselves. Then I would ask what they usually do.

This was incredibly effective. Being honest took away all of my nervousness and allowed me to relax into the conversation. I felt like I had no secrets, I was just telling the truth and asking questions. And I think this works both ways: the person you’re talking to will probably trust you more if you’re honest about what you’re doing.

Just keep in mind the introduction should be short, and they should be doing all the talking. Trust that your research was enough to make people know they matter to you, and then focus on listening.

Final thoughts

What I enjoy most about working in startups is doing a bit of everything and learning a lot. As a co-founder in an early stage startup, this means learning even more and having almost no time to prepare for stuff.

But worrying so much about my lack of time made me actually waste it, because I wasn’t paying full attention to what I was doing.

Learning to have better sales conversations, for me, was learning to create a process I could trust. That got me to stop overthinking everything and paying closer attention to what was actually happening. It gave me much more room to learn, not only about sales but also to improve our product.

I also think learning to listen makes us better people to talk to, and that’s a benefit on it’s own.

Would love to hear your thoughts, you can find us at Twitter to continue this conversation. Promise I’ll listen!

Getting new users is important, but no acquisition efforts will last if you don’t give your users something to stay for. In this article I’ll argue its much more effective to engage your users with drip email campaigns that get triggered from a specific user action, and I’ll show you how to create your own automated drip campaigns based on what your customers are doing with Palabra.

Why focus on retention

If you have a subscription-based business, you are well aware of how important engagement is for your monthly revenue. But no matter what type of product or service you have, having people keep interacting with your site or app is probably really good for business.

Getting a new customer can be 7 times more expensive than getting new sales from your existing contact-base. Focusing on retention also enables you to create long-lasting relationships with your customers, and can be part of your customer experience added value.

Personally, I like focusing on retention because I love talking to users and learning from them. When people respond to our ongoing sequences, I have a much better understanding of what their problems are, and that gives me valuable information to:

What is a drip campaign for retention

As the name suggests, drip email campaigns are sequences of emails sent to get users to a specific goal drip by drip during a certain period of time.

Drip campaigns can vary in terms of frequency and duration, but they all serve the purpose of nurturing users or prospects without overwhelming them with ever-lasting emails.

A well used drip campaign has much higher read and click rates than promotional emails — up to 3 times higher than single send emails. It takes a bit of work to create a good drip campaign, but the results will very much be worth your time.

There are three things to consider while setting up drip sequences to make them work:

Let’s look at each separately.

Measuring retention and defining goals

To create your own drip campaigns for retention, I suggest a data-driven approach: have a clear goal of what you want to achieve with them first, and create the emails last. Defining your strategy before creating your content will save you a lot of time later, since it will give you a clear idea of the content you should be sending.

When it comes to retention, the purpose of drip sequences can vary depending on what retention means for your business. For e-commerces for example, retaining customers means offering more products to the same customers, based on their previous preferences.

For a subscription-based tool like Palabra, our retention goals for first time users are tw:

If you want to use drip campaigns to improve your retention rates, you first need to find a specific goal you want your users to achieve. These goals will be specific to your business and user base, but they need to be very clear. “Getting people to stay around” is too vague.

To create your own retention goals, ask yourself this questions:

I used Amplitude’s guide to create Palabra’s retention goals, I recommend it if you’re starting to think about retention for your product. We also use their tool to measure and optimize our retention strategies.

Content & timing for retention oriented drip campaigns

Once you have your retention strategy defined, you can set up a drip campaign to get users to continue along your user journey.

The first thing to keep in mind while designing a drip campaign is timing. How long does it usually take your users to complete the key action you’re aiming for?

When we created our first onboarding sequence in Palabra, we didn’t really know how long it would take people to create a trigger. So we created our first onboarding sequence just thinking about what we thought would make sense, and ended up with a simple drip of 3 onboarding emails.

After getting our first 20 or so active users, we found out it takes people about two weeks to set up their first trigger. We found that people take time to clean up their strategies after creating their account, even if they have a specific problem in mind that they want to solve.

We were really surprised to learn that, since it takes no more than 20 minutes to actually create a trigger, and only 5 minutes to connect Palabra to Google Sheets. But real users don’t lie, so we changed our onboarding sequence.

Instead of offering help just 2 days later, we wait for a week, to give them time to look around first. And after they do turn their first trigger, we show them other things they can do with our platform, offering them to complete challenges

There is no recipe to create drip campaigns that will work for everyone. The best thing that you can do is get to talking to your users as early as possible, and learn from what they’re actually doing with your product.

After you identify the timing behind each action they make, it will be much easier to set up different emails that lead users to solve their own problems.

Keep in mind what your users are actually doing and not what you would like for them to do. If you don’t have users yet, take your best guess but make sure to improve them after you have real data.

Automation: why and how?

Most drip campaigns are triggered when a person moves through the conversion funnel. Those are usually actions they take to subscribe or buy something. That could be just enough to create your first automated drip sequence, and it’s easy enough to start.

One of those examples is the most common drip campaign for retention: the onboarding sequence. They typically consist on a few emails showing a few interesting features that may be helpful, offering help and asking for feedback. Superhuman has a great onboarding drip that consist of one email per day during the first week to show the basic features, and then some tricks or features 2 times a week afterwards.

To automate an onboarding sequence, you have to set up a trigger based on subscription (or account creation). To do that with Palabra you can choose from many integrations depending on your stack, for example if you have a Webflow landing page, you can send an automated sequence each time someone submits a form to subscribe.

To engage retention from other user actions, you should first think about how often you would need to send those emails before automating. It may be easier to send emails manually yourself if you have 10 or less users that complete those actions each week.

In most self-service products, automation is almost always the best choice. Having a fully automated flow can save you a lot of time once your users start to grow.

For example, if you are selling courses online, you may want to create a short sequence that starts once they complete the course, and show them what other things they can learn on your site. Most online learning platforms (and many other products) connect to Zapier, so you can set up a Zapier trigger to Palabra if you want to automatically start a sequence to re-engage them.

Final thoughts

To engage users there’s no work-for-all recipe. You have to actually take time to find out what it is your users are doing and how you can help them move on to their next interaction with your product. Once you know that and have a clear goal in mind, drip sequences will help you educate and nurture your users without overwhelming them with long emails.

To use drip sequences for retention and save some precious time, you can choose a tool to automate sequences triggered by user actions. Just find out what action can lead to the next one and start with simple sequences to engage your users.

As an early stage product, we are constantly improving our sequences and retention strategies, so I know how time-consuming it can be. My recommendation is that you choose a tool that you’re familiar with or that has a short learning curve to make your first automations. If it takes too much time to learn, automating can take you more time than it saves.

If you have questions or want to share what drip sequences you’re automating to drive retention, just send me an email or ping us at Twitter.