Revamping the Customer Onboarding Experience with Mark Colgan Podcast

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Guest: Mark Colgan is an entrepreneur and revenue leader responsible for increasing revenue across a small portfolio of companies where he leverages his 13 years experience of B2B Sales, Marketing and Recruitment. Mark currently splits his time as Co-founder of Speak On Podcasts, mentoring B2B Startups via GrowthMentor and ScaleWise, The Product Onboarders and coaching 100’s of SDR’s through his Outbound Prospecting course via The Sales Impact Academy.

Overview: In this episode of Digital Conversations, Mark Colgan joins host Billy Bateman to discuss both customer onboarding mistakes and best practices.




You’re listening to Digital Conversations with Billy Bateman, where we discuss using bots to improve your marketing and sales funnel. 

Alright everyone, welcome to digital conversations. I’m your host Billy Bateman. Today I am joined by the great Mark Cogan, co-founder at speak on on podcast and the product on borders. Mark, thanks for joining me today. 

Hey, buddy, great to be here. Looking forward to it. 

Awesome, man, I’m excited. We’re gonna talk a lot about product onboarding, where the pitfalls are, how to avoid them, how you can stand out from the crowd. But before we get into that, you’ve got an interesting journey, and you’re doing a lot of different things. So just tell us a little bit about yourself and in what you’re doing. Sure, yeah, 

it’s quite a mouthful. So especially if you look at my LinkedIn profile. So the long story short is I’ve got around 13 years experience in sales and marketing, mainly in the b2b space. Right now I’m I run product on borders, which is all about helping b2b SaaS companies increase visitors to free trial and free trials, paying customers. I also speak on podcasts, which is helping b2b technology brands like fuel their credibility and authority through speaking on podcast where their customers listen to. 

I do a ton of coaching on the side as well around the sales process. So that’s where you’ll see all my LinkedIn profile. I’ve got the growth mentor and skill wise, and I coach the outbound prospecting course with the sales impact Academy as well. So pretty busy. 

Yeah, busy man. Okay, so tell us a little bit a little bit more about speak on podcast. And also the product onboard is just you know, what do you guys do? What? What’s your ideal customer look like? And and what value do you provide to them? 

Sure. So with the speak on podcast, it’s an agency. So we have a team of dedicated booking agents. And what we do is we help our customers get on the podcast where the ideal audience is already listening to. So we do a ton of research to find the most relevant podcast. And then we reach out to the podcast host with really, really specific introductions, we don’t like to use the word pitches. Because I know you believe as a podcast host, you get lots of pitches every day.  

And so we do our best to stand out from there. It’s not aggressive or salesy at all. But really, it’s a combination of a lot of my experience with outbound sales, and the matchmaking that I used to do in recruitment, as well. So our customers sign up with us. We guarantee a certain amount of bookings on podcasts each month. And we have a guarantee to say you can say no to any podcast if it’s not the right fit.  

I think it’s only happened once or twice, and it was down to more of a personal preference than anything else. So that’s what we do speak on podcasts. And then with the product and borders is also like a product I service. Me and the co founder, Helen, we saw a need that a lot of people are dry. There’s a lot of content around lead generation and top of the funnel acquisition, but there, but there’s just not that much of a focus on activation. And also churn reduction.  

So there are obviously some is some content out there, but it’s in minority compared to the top of the funnel stuff. So we decided to put our heads together. And what we do is we offer a product onboarding review. So we go through a b2b SaaS companies free trial experience. And we’re looking at things like the website. We’re looking at the signup process, the first run experience, as well as the ongoing onboarding and the onboarding emails as well.  

And we just present these back in around 2025 minute video, if I’m honest, is quite brutal feedback. Sometimes we have to give that caveat back to the people we’re doing the reviews for. But we always act as almost like the dumbest user that they will get in their platform, because your product needs to be that simple and intuitive. So we’ve done over 50 reviews. And I think a lot of the things that we’ll be covering today is really a combination of those 50 product onboarding reviews that we’ve done, and the lessons learned from all of those. 

Common handover issues

Great, man. So you’ve done a bunch of these reviews. What are the common issues you see with sales and marketing handover to customer success teams for b2b businesses? Yeah, so this is a really good. 

But then, and this is typically a service that you’re selling. Or, it could be a much larger product that you’re selling as well. So one of the biggest pitfalls that I see is that… Let’s start with why it’s important, you know, to hand over to the customer success team properly.  

And that comes down to customers can feel really unappreciated. Because if their information falls through the cracks, they have to repeat themselves. And that’s never a good experience to have. Especially if it’s the first engagement they’re having with your company once they’ve kind of signed on the line.  

Oftentimes, you see as one I’ve been in this situation as well, that the team can point fingers at each other when something goes wrong. Because no one knows who’s accountable for for what and for what so having that process in place for the handover is really important. And I guess the most important thing when it comes to the onboarding of a new customer is that it’s really is very, very hard to win back the trust of a customer. Once they’ve had a bad onboarding experience.  

And Lincoln Murphy of 16 ventures. I think he coined the term seeds of churn a planted early, and it actually starts and they’re planted in the sales process as well. So maybe I can share some of the best practices that companies can deploy.  

So really, I think there’s, if I could take away four main points. The first is just setting expectations with the customer during the sales process. Let them know what the onboarding process is going to be, who’s involved what’s required from them as a customer versus what what’s expected for you as the business to do? That’s really important.  

And oftentimes, it might be said on the sales call, or one of the one of the sales calls, but a lot of companies forget that the product that they’re selling is just one tiny part of their prospects or their new customers overall job. So they’re not going to remember everything that you say on a call. It’s important to follow up those expectations in written format, so they can always revert back to them.  

Another thing, which I think causes a lot of misalignment. is not understanding how your customers are actually going to measure success. As a business, you might have an idea of what those maybe success milestones or definitions are, but you really want to understand what your customers are defining as success.  

The third, so this is a situation I’ve been in before I was in a sales role, and I was closing deals. And then I just didn’t feel confident that the process behind the scenes after the sale had closed was good enough, not not that the people weren’t going to have a great team. But there just wasn’t a succinct and easy to follow process.  

So one of the things that we did to overcome this was actually have a meeting between sales and the customer success to officially hand over the customer. And it’s all about sharing the little bits of information that your customers have shared with you during the sales process. And they’re really like nuggets of gold, because it could just be one thing, they said at the end of a sentence that you realize that’s really important to them.  

So it’s handing over some of the informal information that you received. Also from the customer success side. And Billy, it might not be a customer success team, it might be your client delivery. Or it could be an account manager. Whoever you’re handing it over to, there should be a standard set of questions which are asked during the onboarding handover meeting.  

As an ex salesperson, it can be, I can feel it, that’s a waste of time, because I just want to go off and sell. But it’s really important to get it right and handover properly.  

I guess the final thing would be to keep the communication dialogue open with the customer. And is often the salesperson that gets the blame if the onboarding process isn’t smooth. That can impact your reputation as a salesperson, and also impact the opportunity of increasing the lifetime value through upsells, and cross sell opportunities in the future. Because it starts to erode the trust of you as an individual. So definitely having that customer open, dialogue open.  

And I didn’t think there’s anything wrong with a salesperson sending an email a few weeks after the onboarding processes started saying, hey, just checking in, how’s everything going for you? Oftentimes, it’s a clear cut handover, and the salesperson never speaks to the customer during the onboarding process, but I really don’t think there’s any harm in doing so. 

Yeah, honestly, I’m with you. 100%. On that, I think any good sales rep, not everybody is, every company pays on renewals, but some do, but you should be invested in Okay.  

Are they actually going to retain, especially in a SAS mark, SAS setting where you’re just like, Okay, I’m gonna get paid for the first year that their customer now maybe they paid annually upfront, and you don’t care anymore as sales?  

Yeah. I mean, you should, but you might not. But if they’re paying month to month, and you get paid as they pay, and they could cancel. Man, I would, if they’re might, if they’re my account, I’m gonna check in with them at least once a month and just at least shoot them a note and say, how’s everything going? Can we help you out with anything? Absolutely. I think that’s just good business to you know, like, make your customers feel the love, like you should love your customers. 

100% and, you know, it’s it’s the gesture as well. So they may not ever reply, but they know that you’re a couple, they if they’re polite, they’ll reply, but sometimes they’re busy, they won’t reply. It’s the gesture that’s important.  

And one thing that I’ve found, personally from my own experiences that I’ve had customers, they work with me whilst working for one company, they get a new role, and then they come back in that new position and sign up again for the services. So I still got their existing account going from the previous company worked out Because they’re still enjoying the service or have a need for the service.  

Then they bring in new business because they’ve just started with a new with a new company. In my in my last role at task drive, we had one customer sign up, we expanded the account to four researchers. And then she left joined a new company came came back to us with two researchers. So that turned into six all because she had a great experience moving, moving through the whole process. 

Onboarding tactics

Yeah, yeah, no, I love it. Now, before we move on to talking a little bit about tactics, I want to dig in a little more on one of the best practices you mentioned, which was, how do you measure success? I know every business is going to be a little bit different. But what have you found works in helping in that sales process to define what success is going to look like? 

Yeah, I quite like asking quite open ended questions to get the answer. So I’m just trying to think in some with some examples. So one of the questions I like to ask is, yeah, what does success look like for you?  

And I may expand on that and say, in a month’s time, let’s just say the onboarding process took them took a month, what is it that you’re you? What is it that you expect from us? At the same time, I might flip that question and say, What does failure look look like? You know, what would we do to get you in trouble? In your role? 

Great question. 

Yeah, and it because, you know, we are working with humans, and people have emotions. And there’s, there’s motivations, and there’s fears, to finding out their fear, or, you know, this is how it could completely mess up their their role in their job, and potentially they could lose a job, especially if it’s a very expensive decision and purchase that they’ve just made the understanding, really, you know, what are they going to be concerned about?  

I had an example with my accountant recently, and they forgot to send me an update before the end of the week, before the end of the week, I needed an invoice to go out. And over the whole weekend, I was panicking, panicking because I didn’t have this money coming in which I wanted to use to do something else. They had sent the invoice they just didn’t tell me until it was Tuesday morning.  

And you know, I saw that email as our call panic over. And we spoke about it with friends, obviously. But it’s like if they had just let me know that that it was taken. It was it was in progress. I wouldn’t have been stressing over the weekend. And it’s just a time. One email is all it would have taken. 

Yep. Yeah, no, you’re right, those small things make it make a big difference. So let’s let’s start by talking a little bit about tactics to improve the onboarding process. So interested to hear what you have to say about that. 

Yeah, I think if you if there is a customer success manager or an account manager, whoever it may be introduced them early in the process, they may not have to do anything, but at least the customer knows that there’s somebody else who’s going to be taking over the reins, once the deal is closed, for example. Yep, that’s quite an easy one. Another one, which is I guess a philosophy in life that I have, even in my personal life is to under promise and over deliver.  

At speak on podcast, for example, we give a timeline to our customers to say this is what’s going to happen by when. But behind the scenes, we’re a week ahead of that timeline, is the opportunity to always be earlier than what we’ve promised. But it also gives us the opportunity of an extra week just in case there’s issues with the onboarding. And sometimes things come up. So there’s a contingency in there as well.  

And yeah, so that ties to probably my third point, which is to create an onboarding timeline. And that can be as simple as just a Google doc or a PDF, which just says, here’s what to expect in week one, this is what we’re going to be doing. This is what we need from you. Week two looks like this, this is what we’re going to be doing. And this is what we expect from you.

And then of course, depending on your service or product, there will be weeks where you’re working a lot in the background. But you don’t need any interaction with your customers, but communicate with them and just say, hey, look, it’s quiet over over on our side.  

However, we are busy working on x y Zed. I think a lot of come in the future forget that. They know the companies themselves and know their process. But the customers don’t know their processes. So and I’ve had conversations again with the sales team, where they said, Well, I’ve told them I told them all on the call that I had two months ago. And then I’m like, they don’t remember, they won’t remember. So just continue to communicate with them until they ask you to stop communicating with them. 

Yeah. Awesome. I love it. I think I love to under promise and over deliver just in everything in life. But creating that onboarding timeline, I think is key, like, you know, your process and you’re just like, yeah, they’re gonna be ready and you know, a month or two weeks or six weeks, whatever it is, but they don’t necessarily know that going into it.  

So setting those expectations I think is is key to keeping them happy in that onboarding process. Okay, so you recently spoke at about b2b SaaS product onboarding mistakes at a SAS talk event. Can you share some of those mistakes and how to fix them? 

Yeah, for sure. So this was certainly more geared towards b2b SaaS companies that had a free trial offer as part of their as part of their go to market and maybe their product, lead growth type business. And what as I mean, the product and borders, we look at the website website, the signup flow, the first run experience, the ongoing onboarding, and then the communication.  

Common mistakes

So I’ll give a real whistlestop tour through a few of these mistakes that we’ve seen across looking at over 50 different reviews. And maybe we can jump into them in more detail if we’ve got time, buddy. Sounds good. Yeah. All right. Cool. So first of all, on the website, I think the number one mistake we see is that they do not have a unique value proposition, or a value proposition that actually explains what the outcome is for the customer.  

I reviewed one just the other day and it was meet the world’s first most intelligent platform. I don’t want the world’s first intelligent platform, I want to be able to solve a problem that I have at the moment. And a lot of companies are very quick to talk about how they’ve got patent pending, or they’ve got a real unique, real unique technology. But as a consumer, I just don’t care, I just want it to do what it says it’s going to do. So have a really clear, unique value proposition. And the next one is social proof. And there’s a few things here with social proof. So some some especially on the homepage, all the testimonials and logos are right at the bottom of the page.  

And if you were to put on any sort of on page analytics, like hot jar, for example, to see the heat map of where people click and you lose them, getting to the bottom of the page. So we always recommend that you pepper, your your social proof throughout the whole website throughout the whole page. If you’ve got those have them at the top above the fold, so people can see that and then scroll down. We also see this is quite common mistake. A lot of people link to their g two or capterra reviews, yeah, as soon and oftentimes not in a new tab. So that’s another one always have things going into.  

And if you’re going to direct anybody from your website, always do it in a new tab. But I would argue don’t just embed it onto your website. So they’re not forced to go away. Because the problem with jeetu and capterra is that it’s information marketplace. So they’re going to see all of your competitors, when you go to look at a kaptara reviews of a particular product. So you may have just had somebody who was maybe a warm lead on your site, they’ve gone to kaptara.  

And they’ve seen three or four other alternatives to your product. That’s just not a great experience and and not a great journey that you’d want your potential customers to go down. So that’s that’s about social proof and opening into new tabs. And then I guess the last one would be about inconsistent calls to actions. So if the main goal for your on your website is to get somebody sign up for a free trial, just have the call to action of start your free trial, or I’m not the copywriter in this dynamic duo, the product on borders.  

And I’m not be happy with that example. But But yet, the point is that the call to action should be consistent throughout the site. And I think there’s when we look at a lot of websites, there’s so many different calls to actions, but they actually all lead to the free trial signup, it’s just they say so many different things, keep it simple. Remove the fact that people need to think they can just click and they can go through 

and know what they’re going through as well. So that would be a quick summary of the website during the signup process. So this is the this is when we’re going to start the free trial. A lot of free trials, either ask for a credit card or don’t ask for a credit card. I’m not here to argue to say which one’s best. But what you should do is communicate if you do need a credit card, tell me that before I get to the signup page.  

If you if I don’t need to add in my credit card, remove the anxiety for me as I go through the signup process because it doesn’t say that I don’t need a credit card either. So just think about again, and again, this comes back to you can’t read the label from inside the jar. The people who the product owners and the founders maybe have designed the website they know their product, they know their system and the way it’s set up. The the average visitor won’t as well. Another thing is just way too much information on the forms really probably just need an email address at this point.  

To get people using the platform don’t you don’t need to ask 20 questions on a form. And one of the biggest things that we see is around delayed email verification. And what that means is with delayed verification, users are required to sign up but they’re allowed to access and test the product. They can verify the email at a later date, usually within seven days, and you would send them an email to ask them to confirm that verification. The reason why we suggest delayed verification is because if you are then forth if I sign up and then you force me to go to my inbox, if I was to pull up my tab now, it’s a Tuesday as well as we’re recording this Billy.

Because HubSpot said Tuesdays are the best days to send out email newsletters, I get flooded with promotions and updates in my inbox. That email to verify the email to verify my login is going to get buried, and I might see an important email from my boss, or I might see something that distracts me. Then because I was just about to start a free trial, I’m now distracted, I may not come back to that free trial. So definitely think about adding in adding in delayed verification.  

Moving on to moving on to the first run experience, you really need to think about what your customer is trying to achieve when they’re logging in. And they’re going through the first run experience. Oftentimes, you fill out the signup form, and you just get an empty screen, and you don’t actually know what to do next.  

Again, from a design point of view, the designer knows what to do next, but the average user doesn’t. So you need to tell people what to do with a quick tour, it might be a video, you could use in app messages from intercom or any of the other sort of onboarding software that’s out there just to prompt users to, here’s what you need to do now. So that’s really important. And we often see a lot of companies don’t have that in place. Another great thing to see now, the consumer expectations is always changing. But it’s I don’t believe consumers in the b2b space have ever been as hard. 

Planning as they are now, as we used to net fit, Netflix, and Spotify, and even things like Facebook, and Twitter. These are all set. These are all software that we’re used to as consumers. And they make it super easy for us to use the products and the platform. And in a way that b2b buyers expect the same sort of experience as well. So an example of this, let’s say you’re a graphic design software.

And I’ve been on your website looking because I want to build a LinkedIn banner. Now if I sign up on that landing page to build links to get started with my LinkedIn banner, I really don’t want to be directed to the dashboard, where I have to then click on design, then click on new, select a template, which says LinkedIn, banner, LinkedIn, and then LinkedIn banner template, you know, who will information you know, my intent, so helped me get to that a lot quicker.  

That’s just an example to talk about segmented onboarding. So looking at that landing page, I think and where what they’re trying to achieve. Or it might even be the persona based signup process. So during the, during the initial signup, you might say, Are you a marketer? Are you a founder, or you’re a product manager, based on that you can then segment the onboarding, to highlight the things that those people are most likely trying to achieve in your product if you serve all of those different audiences. Yeah. And the final thing that I could share today is the demo data. So I use the example of hot jar earlier on, if you were to sign up to hot jar, which is a website analytics company, you have to install their JavaScript on your website.  

Now, if I’m the where, if I can do that on my website, I can do that quite easily. But not everybody that signs up to your free trial is going to be able to implement that straightaway, they might have to send it to the dev team, I used to work at a footsie 50 company, I don’t know how long it would take for me to actually get a script installed on the website, as a marketing executive just testing out a new tool. So the oftentimes, the challenge there is the data and the value that people can experience from the product won’t actually be realized straightaway. 

So what companies should do is give them demo data, show them what their life could look like, or what their data will look like, once everything’s plugged in. And once it all the data’s piping into the platform, and rather than just being logged in, being told to email it to a developer and then go, Okay, well, that’s eight weeks. I’ve got to wait to get started on the website. So I’m having that demo data. I’m just helping people explore and navigate and get used to the functionality is is really important. They’re awesome. 

Yeah. Should I keep going? Let’s do it. Should we fall? Yeah, 

let’s, uh, let’s, I mean, okay, the one thing we haven’t covered that I am interested I love all the points you’re making is the emails with onboarding sometimes, I’m like, I’ll sign up for you know, I sign up for a free trial, all kinds of tools, you know, just see where we can get better. Sometimes I love the email, onboarding. And other times I’m just like, either I didn’t get anything or I get way too much and Leave me alone, you know. So what do you guys find find works well with, with email onboarding? 

Yeah. So one of the things that we were shocked to see is that a lot of the email onboarding that we received wasn’t actually personalized. So I put my first name in when I signed up, but just was addressed to Hi there. Another one, I wish I couldn’t help but laugh, it said, if you have any questions, just reply to this email.

And then it was a no reply email address. So I did it, I hit reply, and then I got bounced back to say, your email couldn’t be delivered. And it’s just like, what a bad experience is, me as a potential user who’s going to be paying to use the product. In fact, actually, I’d put my credit card details in and they were charged, so it was a paying customer and still couldn’t get the help I needed.  

But going back to your going back to your point of too much information, we see that a lot. Again, as the with the onboarding emails, people think well, they need to get to that aha moment as quickly as possible. But if that takes five steps, you don’t want to say to them in one email, do these do these five things, just start with the next step.

And that that next step might be the first step it might be install that JavaScript, it might be connect your LinkedIn account if you’re a social media scheduling tool, for example. So it is tough with these emails, because those emails have a job to do. But you’ve got to remember that your user also has a job to do. And it’s just to get to the next step in the onboarding process. 

Product onboarding approach to service-based business

Awesome. Awesome. Okay, man. Well, we are running out of time a little bit, but I wanted to hit one more thing. So one of the things we talked about before getting on was that you’ve taken this SAS product onboarding approach to service based businesses. So I want to know why you made that decisions and decision and what are some examples you can share of successes and failures? Sure, okay. 

I’ll keep this brief, Billy. So as I mentioned before, a poor onboarding experience creates unhappy and frustrated customers and their unlike renew, and they’re probably not going to, they’re probably going to tell other people about the disappointing experience as well. A little bit like I shared a few examples, obviously didn’t name drop any companies. But that that does happen. You don’t want that bad word of mouth to be spread. In fact, we want to create the opposite. So we use almost like event based triggers. Even though our onboarding process is manual. When we reach a certain stage, when we’re onboarding a new customer at speak on podcast, we then send an email.  

Now it’s not automatic, we have the template, but we always make sure that we’re communicating with the customer. As soon as they go through the various different stages. I have actually introduced a onboarding drip email sequence. So classic, Day Zero is welcome. It’s got a team of the team, picture of the team. In fact, it’s a gift we’re waiving, really glad to have you on board. Here’s a link to your timeline.

This is exactly what we’re going to do over the next four to five weeks, then the next email was seven days later, is giving people equipment recommendations, because that’s often a commonly asked question we get from customers, what microphone Do I need to buy? What else do I need to think about when it comes to my setup? day for day 14, we invite them to a practice interview with our with one of our co with my co founder.  

So they can actually go through what the experience will be like once we put them onto a podcast, the 21 is perfecting your offer and your call to action, and also advice on how to actually prepare for interviews. At this stage. We haven’t booked them on any show just yet. But we’re just kind of pre empting the questions they’re going to get.  

And like I said, having that document, which they can look at any time saves them having to email me saying Hey, Mark, what’s the next steps because they don’t just refer to the onboarding document that we share. And we we include a link to that in every email that we send in the onboarding process, because we know they’re busy. We know they’re not going to be kind of starring and saving that, that email or documents, so we make it easy for them, so they never have to ask a question. 

Awesome. I love it, man. I love it. Mark, this has been amazing. appreciate you taking some time to share your knowledge with us before I let you go. I’ve got two more questions. So you’ve looked at a lot of onboarding process. I don’t want you to say hey, these people have an awful process. But what are one or two products that you’re like, Hey, I loved this onboarding process. We think it’s amazing. 

Yeah, so there’s wave. 

I’m not sure if they could send you the link after Billy, their invoicing platform. They do onboarding very, very well. They have three use cases. And they segment the user as they go through the onboarding process. And then the other one I just signed up to the other day was home run. It’s a recruitment platform, or applicant tracking system.  

How I enjoyed the process, not because I geek out about onboarding, onboarding processes, but even as a general user, it made it so easy for me to go through And put in my first job publisher. And the trial lasted 14 days I paid on day one. It was just such a great experience I upgraded because I saw the value of upgrading to unlock some very clever features that they keep behind the paywall paywall, so yeah, homerun was fantastic. 

Awesome, man. I love it. So if people want to reach out to you and continue the conversation, what’s the best way for them to contact you, Mark? 

Yeah, sure. So LinkedIn is probably the best place let me know that you listen, you heard me on the digital conversations podcast. And if you want to find out more about speak on podcast where it’s bigger pockets calm, and the product and borders is the product on borders comm I like to keep things as simple as I can. So So yeah, reach out to me on any one of those. 

Okay, awesome, Mark. Thank you, and we’ll chat later. 

Cheers, buddy. Take care. Bye now. 

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