How Arrows sharpens their onboarding conversion

What is your strategy for onboarding your high-touch customers?

You spend real money on marketing and sales to acquire customers—but if you don’t have a robust onboarding plan, you could easily lose them.

In this interview, I sat down to chat with Shareil Nariman. Shareil recently joined Arrows as the Head of Customer Success and leads the customer success, onboarding, and experience efforts. Shareil previously led customer lifecycle management programs, including onboarding, at Sprout Social, a tool that enables brands to engage with their social audiences. Prior to that, he led operations teams as large as 18 employees at, and spearheaded an upsell adoption effort for the company’s BookingSuite division, a portfolio of SaaS advertising and property management solutions.

Arrows builds tools for customer success and onboarding. It is a collaboration tool designed to help you better communicate to your customers what needs to happen and when it needs to happen in order for them to get the full value from your product or service. This is especially important during the onboarding phase of the customer journey and that’s exactly where Arrows is focusing its efforts today. SaaS companies use Arrows to create mutual action plans that move their customers through those critical early-lifecycle milestones and beyond.

Oprah meme, you get onboarding

I asked Shareil to tell me more about Arrows, their product, and their strategy for trial-to-paid growth. Check out our conversation for his insights (And don’t forget to follow him on Linkedin and Twitter).

About Arrows

Kareem: Thanks so much for sitting down with me, Shareil. Can you tell me a bit about your company, your product, and your trial?

What Arrows Does

Arrows is a customer onboarding software tool. At its core, it’s a collaboration tool. We’ve built it to help you better communicate with your customers, and it’s specifically designed to start with the onboarding phase—especially for your high-touch customers. The idea is that you want to make sure that your customer realizes the initial value of your product or service.

Arrows helps you move your customers through the important milestones that you need them to accomplish in a way that is easy for them to digest. It lets you create a plan that you can share via an easy-to-access link. It helps your customers see what they need to do today and helps you get them to do those things. And if they don’t do those things, Arrows helps by sending reminders and nudges, encouraging them through the process.

Our bigger, long-term vision is a communication tool for the full customer lifecycle and moving customers through it.

Learning and Optimizing Your Onboarding Process

I mentioned that we’re focused on onboarding for high-touch customers, but the goal is by no means to remove people from the process. Instead, the goal is to make those people more effective. We want to help you learn from your onboarding process and optimize it—help you clearly see where customers are getting stuck. And that is part of the opportunity: it lets you then work with your Product, Design, and Marketing teams to improve the UI, user experience, or content—whatever needs to be changed to help your customers move through each of the pieces. We believe the sooner you do that, the more likely your customers are to grow with you, stay with your product, and add more value.

I like to say that onboarding never ends. I don’t like to assign it to a particular timeframe—it should keep going. But it has to start somewhere. And you should have some milestones that indicate progress is being made.

How Arrows Does Trials

We are currently offering a two-week trial. We’re finding that two weeks is enough for our customers to play with the product, build some templates, and test it out with customers. No credit card is required upfront. And we offer both annual and monthly plans.

Arrows Is Early Stage

We are very early stage. We got our seed round funding early in January of this year. We’re currently at seven total employees and looking to get up to ten by the end of the year.

The “Aha!” Moment for Userflow Trial Users

Kareem: What’s your product’s “Aha!” moment and how did you figure that out?

Yeah, so I love this question. I’ve been working on onboarding for 10 years or so now and the “Aha!” moment is so important.

In Arrows’ case, there are two.

“Aha!” Moment 1: Creating Your First Onboarding Flow

The first is when you realize that the product itself lets you create and optimize your actual onboarding flows—whether they already exist or you’re building them from the ground up. As you lay out the steps in Arrows, you begin to see that flow.

“Aha!” Moment 2: Seeing Customers Moving Through the Flow

The second is when you put that plan into action, and you actually see your customers chipping away at that plan and moving through your flows. It quickly validates its value by reminding you what you’re using it for.

And on the flip side of that, it’s an easy-to-use experience for the customer. So you notice that they are more likely to show up to the onboarding call and they’re more likely to do their homework—the steps in between those calls.

And if they don’t do their homework, at least you’re noticing where they’re getting stuck. So it gives you better insight into customer engagement that didn’t exist before. And I think when customers see that they click: “Oh—it’s the plan-building, but then it’s also how customers are engaging with it.” Once that clicks, they come back to add more customers, add more plans, and add user seats.

Matrix meme getting customers through onboarding

Figuring Out the “Aha!” Moments

Kareem: Yeah, that makes a lot of sense. How did you figure that out? Did you look at some data or did you intuit it?


When I showed up at Arrows, I started by watching “game tape”—recordings of customer conversations. I saw customers verbally saying, “Oh, this is a current pain point in my process.” And so I unpacked those moments—there were two or three of them— and saw it was around that setup piece, and then the communication with customers piece.

When I realized that that’s what customers were clicking with, I actually used Arrows to build an onboarding plan for our customers. And so then I validated by seeing if customers were getting past those “Aha!” moments that I pulled out.

So part of my plan was to get users to build their first template. Then I validated the “Aha!” moment with data. Once I saw templates were created, then I saw them being attached to customers, and then saw them being sent to customers, I could see customer progress happening.

So it was a combination of intuition from having worked on onboarding for so long and the data to validate it.

And now I can see all the customers going through Arrows—where they are (or aren’t) getting stuck. And if there are common pain points, I can dive in and fix that part of the process.

Kareem: Right. It sounds like an incredibly useful tool. I run a SaaS with a business partner—we sell to Product and Customer Success teams to help them track and organize feature requests. And, you know, each of our customers succeeds after signing up to varying degrees. And some people just get stuck. We’ve got some data, but we’re flying a bit blind. Actually having a map set out, and having the customers be able to chip away at it, with nudges, would be super useful.

Deciding on Onboarding Flow Steps

So what’s the process you used to decide on the current steps in your onboarding flow?

LOTR meme one does not simply choose an onboarding ux pattern

I mentioned that I watch tapes and I join demos. I do the onboarding piece and I talk to customers.

Then I started laying out every single step that you could do. I did some roleplay with a colleague where we walked each other through Arrows and figured out the best way to do onboarding.

We started with the Aha! Moments as destinations. Then we layered in the steps that need to happen immediately and that are critical. For example, if you can’t log into Arrows, there’s no world where you can create your first template. If you can’t create your first template, there’s no world where you can send it to a customer. So we drilled down to those absolutely critical pieces.

Then we tried to remove obvious bias. I think this is where a lot of onboarding falls apart: when you think your tool is designed well, or you think it’s incredibly intuitive, or you think your text is super clear to customers. But it’s not always as clear as you think. So we tried to take that bias out and imagine we’re onboarding someone who knows literally nothing about the tool.

(Editor’s Note: It’s critical to understand how people who are unfamiliar with your product understand your onboarding flow. If you need a hand with this, I can help you with an onboarding UX audit.)

Then we took all those steps and laid them out in an action plan. That helped us understand how many steps it is in total and how it will fit into the timeframe. It also helps us understand which steps are critical now and which can wait. For example, I have an Arrows plan that maybe has 30 steps, but I know it’s critical to get the first three things done.

Explaining the “Why” to Customers

And then we also make sure we explain the why. In general, I think we spend a lot of time teaching people how to do things, but not teaching them why they should do those things. So I try to layer the why into the onboarding—bringing it back to the job to be done and the problem they were trying to solve in the first place.

This is also where you can get into more of the product-led world and have your tool do some of these things. When you understand what the critical pieces are, you can use in-app modules, pop-ups, or even emails to nudge your customers.

Where the steps were a bit more complex, we had to look for other options. So we considered if a piece should be broken into multiple steps, or maybe put in some video tutorials or a speaking piece to help walk people through it. Again, focusing on that why for our customers. Because if you don’t understand why you should do something, you’re less inclined to worry about how to do it.

At Arrows, we have a left panel where we write your goals—the initial things you told us you’re trying to accomplish. And that serves as a constant reminder as to why you should complete these steps. And I love that piece because it seems so obvious. In the back and forth of emails, you can forget why you even signed up for a tool. And that makes our customer a churn risk and leaves us as just a line item on someone’s P&L.

That’s what we try to avoid. I think onboarding should try to teach that initial why and get that value across. If you do that long enough—and well enough—then you can automate. You can take those how-to steps and put them in a quick plan or an email or a self-guide people through it.

Designing an Individualized Onboarding Plan

Another consideration is the way people want to learn. Not everyone wants a one-to-one onboarding, not everyone wants a webinar, not everyone wants self-guided onboarding. So my goal is always that 100% of customers should get onboarding. But what that means is that 100% of customers should have an option to get onboarded in a style that they like.

I’ve created plenty of on-demand webinar content, but I don’t learn that way. I would never attend that type of webinar to learn. I want to go in on my own, play, and click around. Give me some resources and if I have questions, I’ll follow up.

Kareem: Right. That’s where the expansion revenue is earned (if your model works that way.)

Yep. And the sooner that expansion happens, that’s how you impact customer lifetime value.

I was actually building a calculator the other day to compare the CLV when growth happens at month one versus at months three, six, and no growth. And that whole premise is to get people out of this mindset that customer success is a cost center. It’s not—it’s a profit center. It actually helps retain customers.

We spend so much time focused on customer acquisition costs and very little time spent on customer retention costs. That’s where all the money is. That’s how the growth happens.

Bill and Ted meme proper customer onboarding

Successful Strategies for Improving Trial-to-Paid Conversion

Kareem: Completely agree. What are the one or two most impactful things you’ve done to improve your trial-to-paid conversion rates?

Strategy 1: Use Our Tool to Onboard and Show Customers its Value

I’m lucky in that my product is for onboarding—that’s what customers are coming to us for. So I use Arrows itself as the onboarding mechanism. If you sign up with me, you’re getting an Arrows plan. That means you can see what your end-users are going to see. You’re also getting a sneak peek into that customer experience—you can see a well-designed plan. And that’s encouraging you to go in and build your plan or share it internally. So now you’re hooked. That’s the first step.

Strategy 2: Follow-up

The second piece is a little bit more human (although you can obviously do this in an automated fashion as well): it’s checking in. So again, I can see where users are getting stuck and I just quickly reach out. I can comment through Arrows because we have a comment functionality in there. The idea is to keep users in the Arrows ecosystem. But if that doesn’t work, I’ll email customers just to check-in or to offer support.

But what I find there is that it’s less about restating the value and it’s more about helping them get unstuck. Maybe they need some hand-holding or maybe they’re that type of learner that needs a little bit more from me. So it’s leveraging the tool to advertise itself in the trial.

Strategy 3: Use Customer Feedback to Improve Product

Third, we make sure we learn from our customers, even if they don’t end up subscribing. That’s where I’m getting most of my product feedback. Then I turn around to the Product team and get those features built.

And then I try to keep those people in a pipeline where I follow up. Or I try to get them to subscribe to our newsletter because that’s where I’m sending monthly product updates and shipped features.

So it’s okay if it didn’t work for them, I just want to understand why. Maybe it was completely the wrong fit or tool. But I want to learn from those trial experiences—what customers are doing, and, I think more importantly, what they’re not doing. And then building on that. We’ve been able to modify our email reminders, the tool itself, collapsible phases, the way plans are shared—all from learning from that short trial phase.

(Editor’s Note: Moritz from Refiner also notes the importance of learning from your customers to understand what works and doesn’t work. Check out my interview with him for more on this).

Strategy 4: Keep Them Engaged with Content

The other piece is content.

Anchor Man meme content its kind of a big deal

For people that are doing the trial on their own, having those resources and content on-demand is critical. Again, it needs to be a combination of the “how-to” as well as the “why”. I write a lot of the blogs and articles that end up on the website to encourage people that are in that ecosystem to use the product on their own.

And then to take that a little bit further, we build content that sits adjacent to our actual product. If you’re not ready to signup, I’m giving you email templates of how to introduce onboarding and how you would lay out those steps. I’m giving you value calculators and templates… we even have a downloadable success plan that gives us a lot of traction on our website.

That type of content helps people see the value in your tool. Even if they don’t convert today, it’s a reminder that Arrows exists. And you’ve signed up for a drip campaign or a newsletter by downloading one of those pieces of information.

We’re actually seeing a decent amount of return trial-ers from that. Maybe it wasn’t the tool they needed six months ago, but they saw new features in this month’s newsletter and decided to give it a shot.

Kareem: I’ve heard that referred to as pre-boarding content. You provide related or adjacent content to help people understand how to solve their problem well, manually. And then if they want the “fancy version” because the manual version is painful, they go to the source that gave them the manual version—you.

Trial Structure

Ya. We’re still thinking through the trial piece. It’s more of an ask at this stage—I don’t think it’s super well advertised. But customers are scheduling a demo, and then they’re asking for the trial. We’re finding that about one out of two customers asks for the trial. The others get it right away. Our price point is affordable enough that people feel comfortable coming in monthly and testing it.

We charge $100 for your first seat, and then $25 a month beyond that for additional user seats. And we don’t limit how many templates you create or how many customers you send to or any of those things. So most people just seem to be saying, “Cool, let’s do this.” And then we go into onboarding and consulting.

For the ones that are asking for a trial, we turn on their account and just don’t charge them. It’s the same product without any limitations. I manage it through Arrows (they sit in a trial phase for me). And then I keep them in a separate pipeline in HubSpot and I follow up with them periodically. I also make sure to check in to collect feedback and, if their feedback or requests align with something we’ve launched or shipped, I can follow up and reach back out to them.

And then another thing that I’m offering people in the trial is a drip campaign for onboarding. It’s a one-on-one guide with tips. So even if you don’t use the tool today, you showed enough interest in the customer onboarding space, so I know there’s some desire there. Then throughout that drip campaign, there are entry points back into the Arrows ecosystem. I’m not pushing you to demo—you’ve already done that—but that’s where that adjacent content comes in.

Napolian Dynomite meme subscribe to my newsletter

Kareem: Content is useful across so many dimensions, right? It’s useful from an acquisition perspective, from a nurturing perspective, and then also from a getting unstuck and seeing value perspective.

The Arrows Toolkit

What are the key tools used to measure and improve your trial-to-paid conversion? You use Arrows, obviously. But what else do you guys use?

To be honest, conversion is not really a problem for us, per se, because we don’t offer a true trial on the front end yet.

In the past, I’ve used Pendo and Intercom to engage with customers in a scalable way. They help you let users know there’s someone here to help you.

Another thing I do—it isn’t a tool, per se—but I offer consultations for building strategy during that trial period. That has helped me convert.

Our customers come to us through chat or through ConvertKit. But yeah, I don’t have enough people in the trial to really need many tools at this stage.

Kareem: So it’s highly manual at this point, which seems like the right place to start. See what works and what doesn’t, and then automate, once you’ve figured that out.

Ya, for the volume we’re at we don’t need it. Obviously, if you have 1,000 trials signing up a month, I wouldn’t approach it manually. There should be tooling behind that, with metrics and data. You should pay close attention to it because it’s a first impression that you might not get to make again.

Kareem: Do you ever use screen recording software like FullStory? You mentioned game tape—was that just listening to customer calls?

I’ve used FullStory in the past, but I don’t use it at Arrows. It’s absolutely useful seeing what customers are doing, where they’re getting stuck, and why they are getting stuck.

FullStory is a great tool because you can compare customers who are actually subscribing to those that aren’t. So you have a control group. It can help you find something in your app that highlights where that disconnect happens for some customers. And it might be multiple places, but you’re gonna find something by clicking around in there.

And then you can follow up. You can ask a simple question: “What one feature would have kept you in here a minute longer?” or “What one thing would have gotten you to log back in a second time?”

Learn from that. I think so many people glaze over trial users and go just to customers, but there’s a lot to be learned from trials.

Kareem: For sure. You mentioned HubSpot—Do you use that for your support tool or your CRM?

I’m using HubSpot for both at the moment—and a little bit of marketing. We were using Streak at first, but we outgrew it and changed to HubSpot. And we’re on our way to Salesforce. We’re building a Salesforce API, so it’s just a matter of time. It’s just a little pricey for what we’re doing at the moment.

Kareem: For email marketing, you mentioned using ConvertKit—is that right?

Ya, I’m using ConvertKit at the moment. It ties nicely to the forms on our front end so I can understand where customers are entering from and what they’re looking for.

And that is something I’ve updated recently. We have five different entry points on our website. And I noticed one of them kept getting unsubscribes. ConvertKit would tell me, “Okay, in these four entry points, people are coming for onboarding tips or strategy. For this fifth point, people are actually coming for a downloadable template and they don’t necessarily want tips.”

So now what I’ve done is I’ve added a second layer for that entry point where we’ll send you the template. Once you open the template, we send a follow-up email through ConvertKit that says, “I saw you downloaded the template. If you want tips on this, here’s a link to sign up for that drip campaign.” We’re noticing that there is actual conversion there. It’s not everyone, but we’re also conserving that first impression.

Outstanding gif

Inspiration from the SaaS Community

Kareem: Yeah, that makes sense. Last question: who’s one person you follow online to learn how to improve trial-to-paid conversion?

Well you, now, after reading some of your website.

I will say I haven’t paid a ton of attention to who’s talking about this online. But I am in all sorts of Slack communities from the ProductLed Institute to customer success and education communities. I’ve also done podcasts with some people in the product-led community.

I’ve also learned from a lot of internal marketers. I’m big on cross-departmental collaboration. In customer success, I believe you should be always talking to Sales leaders, Marketing Leaders, and Product leaders. So there is a lot of that knowledge that lives inside your organization potentially already.

I also follow @SamuelHulick and @louisnicholls_.

The Big Takeaways

Here are the major takeaways that I took from my conversation with Shareil:

  • The value of “game tape”. Shareil watched recorded customer conversations to understand where the value was and to identify the “Aha!” moments. This helped form the basis of a successful onboarding flow.
  • Customers need to be led through onboarding. Having a plan helps you do that effectively. (And creating that plan is exactly what Arrows is built to do).
  • “Customer success isn’t a cost center—it’s a profit center.” Shareil emphasized the value of good customer success in converting trial users to paid customers and then retaining them. This is important to remember—It’s easy to focus on customer acquisition and underestimate the value of a robust customer success strategy.
  • Collect customer feedback. Shareil highlighted something I’ve written about extensively before, which is that collecting customer feedback is critical. It helps you do a number of things including improve your product and polish up your onboarding strategy.
  • Content can keep non-subscribers in your orbit. Shareil points out that sometimes your product isn’t right for a customer today, but it will be in 6 months. Keep them around with newsletters and product-adjacent content that provides them real value.

A huge thank you to Shareil for the great insights and a behind-the-scenes look at a growing company with a fantastic product. Don’t forget to give him a follow on LinkedIn.

Want to develop a conversion funnel that’s as successful as Shareil’s? I can help.

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