AA 41 | Onboarding Clients


Onboarding a new client may only take an hour or two, but it can easily take half of your day if you have to travel miles just to get to the client. That means hours of unpaid travel time that could have been saved with cloud accounting technology. Joining Michelle Weinstein to talk about this is cloud accounting specialist and podcast host, Blake Oliver. Having had to endure the long drives himself, Blake realized that you could actually save a lot of commute time if you can incentivize the client to go cloud-based. He gives us some essential tips on onboarding clients and coaxing them to embrace the virtual model and remote work setup.

Listen to the podcast here:

Using Cloud Technology To Onboard New Clients With Blake Oliver

We have a very special guest. He is a CPA who specializes in cloud accounting technology. He is also the producer and co-host of a weekly show called the Cloud Accounting Podcast. He also occasionally posts an article on his Cloud Accounting blog. In 2016 and 2017, he was named the CPA Practice Advisor’s 40 Under 40 list. Before we welcome our very special guest to this show, I would like to take a moment to thank our reviewer of the show. The reviewer goes to Gayathri. She or he says, “Inspirational and encouragement. This podcast gives me a reason to believe in the value I’m giving to my clients. Michelle always gives the right message to do it more and do it better. Thank you.”

That is true. The main purpose and mission that I have for you are that you get paid every single dollar that you’re worth. We talk about that because our special guest shares the story about how he didn’t charge his client for some travel time. You never want to leave money or dollars laying on the table. All of that goes into your pocket only. I would love to highlight one of your reviews in a future episode right here on the Abundant Accountant podcast. I would love to know what is the one thing that has helped you from listening to this podcast that you’ve implemented in your firm. Share with me in a review that one thing so I can make sure that I continue delivering the content that you want and love.

Before we welcome our very special guests, Blake, to the show, I would like to thank our sponsor for this show. This episode is brought to you by Xero. With Xero, small businesses and accountants can work together at anytime from anywhere with real-time financials, bank connections, unlimited users and online invoicing. It’s beautiful accounting software that’s easy to use. Visit Xero.com.

Let’s welcome Blake Oliver to the show.

Thank you so much for having me. It’s great to be here.

I am super excited to have you here on the show. I’m very excited to talk about making people’s lives more efficient so they have more time to go sell. We’re going to be talking about how to onboard new accounting clients, how having maybe cloud software can help you out. I know a lot of you have shared with me that working remotely is super important. Blake, can you share with everyone a little bit about you? Even though I did your intro, it’s always better to know it directly from you.

I am a CPA, but I didn’t start out in accounting. I was a Music major in college. I played the cello. I thought I was going to be in an orchestra. I wanted to be in an orchestra. I picked up bookkeeping after I graduated as a way to pay for my auditions. I was practicing and taking auditions for orchestras. I was doing bookkeeping as a day job. I quickly found that there was a lot of demand for my services as a bookkeeper. I was pretty good at it and not as much as a musician. Over time, I got more and more into the bookkeeping. I got into the tech side doing QuickBooks and advising with Xero, all the tech stuff. I liked that and there weren’t a lot of people doing it.

Eventually I said, “I like this. People are willing to pay me for it, so maybe I should go back to school and get my CPA.” While I was doing that is when I started my online accounting firm. We were doing bookkeeping accounting. It was called Cloud Sourced Accounting. That was what launched my career while I was in school studying for the CPA exam. We were one of the first firms using cloud accounting tech and latched on to tools like Gusto, Bill.com, Xero, Practice Ignition, Expensify, Hubdoc, you name it, we used it.

AA 41 | Onboarding Clients

Onboarding Clients: Have somebody on your team whose only job is to onboard clients.


You had a bunch of monthly service expenses.

We were doing ongoing monthly accounting for about 200 small businesses. We had 200 clients but probably 120 monthly clients. We’re a team of twelve and we did very well. We grew fast. Within a few years, I was able to sell that practice to a CPA firm. I went and took some time off and got my CPA. That was my life in the accounting world. A few years ago, a software company approached me and said, “Blake, we think you might be good at this thing called product marketing,” which I had never even heard of. They said, “We pay you to create content for us, to do webinars and create CPE.” I said, “That sounds cool,” because I was doing it for free on the side. I went over to a company called Flowcast and I was doing marketing for them. I then joined another company called Jirav. We help accountants become advisors. We give them the tools to do that. I’ve been having a lot of fun doing that. I also have my podcast, the Cloud Accounting Podcast.

It seems like you’re busy, but I want to go back in time with you because I know that onboarding new accounting clients is a hassle for a lot of solo accountingpreneurs. One of the questions that I hear most often is, “How do you streamline that process?” I help with the lead conversion and the sales conversion piece. If you can’t have a clean and streamlined process than the sales piece, it’s going to be a little hard to deliver on. This is a big-time sucker for a lot of people that don’t have a system in place. I would love to talk about at least three good strategies to make onboarding new clients go way more smoothly and quickly that you figure it out. You were able to grow to 200 small business clients and eventually sell your piece of business, which I know that’s an exit strategy for a lot of our audience. For you, share with us that headache client that said, “I need to have a bunch of different services that I’m paying monthly so this process is streamlined.”

I’ve onboarded a lot of clients. I have some horror stories, also success stories, but I learned from those mistakes.

We always learn from our mistakes. Let’s hear about that one horror story. We can walk through the process of some of the learnings that you figured out. Maybe some solutions that you’ve learned from that experience. I’m sure for that accountingpreneur tuning in like, “I’ve got that horror client that I can’t deal with ever again like that.”

The biggest problem I ever had was with one of my largest clients that I obtained as a freelance bookkeeper and that was an investment advisory firm in Santa Monica. They were on Ocean Boulevard. It was slightly under $50 billion in assets. Believe it or not, they were doing all of their accounting in QuickBooks, which is possible for an investment advisory firm because they don’t have a ton of transactions, just a lot of dollars that they oversee. The CFO there wanted to convert to online. I engaged with him directly to convert them from a desktop accounting system to an online accounting system. It’s pretty straightforward. It wouldn’t be challenging because they’re relatively big customers. It was one of the biggest deals I’ve ever done.

I felt, “Based on the volume of transactions, what I’m doing, they may be bigger, but it’s not any more complex than any eCommerce client that I’ve migrated.” The big mistake I made from an onboarding perspective with him is that there was an in-house bookkeeper that was going to be involved in this whole process. I never spoke to that person before I made this deal. That person ended up being very resistant to change and essentially derailed that project. Going back to the original scoping of the deal and the sales process, I learned from that. Always bring in all the key people that will be in the project and make sure that they’re on board because otherwise they can drag their feet and the project will never happen. It doesn’t matter whose fault it is. If the project fails, that’s a failure.

AA 41 | Onboarding Clients

Onboarding Clients: Make sure your clients are okay with the virtual model before you proceed with the onboarding process.


It’s the same thing in sales too. If you don’t have all the decision-makers present, it’s very similar to this because now you’ve got this resistant person who doesn’t even want to implement it. That does sound like the beginning of a massive horror story.

I learned something from that, which is always bring in all the key stakeholders as early as possible. Even if they’re not involved in the buying decision, anybody that’s going to be part of that project needs to be bought into the whole thing for onboarding to be successful. It was nice in that I did get paid. Unfortunately, sometimes we don’t get paid when things go wrong, but it was disappointing that what I’ve created never got implemented. I got paid a lot of money to do this, but it felt pointless. A lot of accounting can be that way though so I didn’t feel too bad about it.

In addition to bringing in all those key people on a project because that’s super important, what about having an onboarding checklist or any other dedicated resources that you’ve used that you’ve learned? These are the other things that if you want it to go smooth and not into utter chaos, what are 2 or 3 other things that you would layer onto that?

Having training available for that individual who became a block to the project would have been helpful. I didn’t have that at my firm at the time. It was just me. I didn’t have the capacity to do the extra work to then get that person trained up and bought in. It would have blown the project out of the water. That is something for firms that I always say, “Make sure that you have somebody on your team who it’s ideal if it’s their only job is to do client success. Train them on any new systems that you’re putting in so that they aren’t confused. They aren’t scared. They know how to use it.” A lot of times we go in and we’ll rip out systems and put new ones and we won’t do training on the client-side. They try to do something. They can’t and they’re frustrated. That can create a lot of problems. Related to that having the training person is also have people on your team who are dedicated to onboarding.

This is where I succeeded in my small firm. I hired a guy whose only job was to onboard clients after the sales process. He wasn’t even involved in sales. He wasn’t a sales guy. His job was to receive the sales orders and implement all the systems. First, get the client set up on our billing system. Get them in our project management system. Make sure that all of the tasks have been created for everybody. Set up all the apps and do the basic. He wasn’t an accountant, but he could do the basic import of the initial transactions into the accounting system. Get all the files and all that stuff that has to happen, he would do that. It was great because he didn’t do ongoing accounting work. He wasn’t distracted by the monthly close cycle or payroll or bill pay. He could focus on for three days and all I’m going to do is bug this business owner to get what we need to do our jobs.

It sets them up to win. You don’t have a situation where you had that person who is not only your blockage but then the project didn’t even get done. You got paid but you weren’t able to see it all the way through. No one here wants to sell services and help their clients and then not see it through. Having the people dedicated to onboarding. Who in your firm is going to be Kirk and the right training for those people too? You set it up once because if you have it set up once, then they can continuously use it over and over again in your firm when you bring on new clients. I’m a big advocate for that.

He got fast because all he was doing was conversions and mostly conversions from desktop to online. He got fast at doing it. It was amazing how efficient he could be. He would package up everything nice in a bow and hand it off to the bookkeeper and the accountant who would do the ongoing services. They were so happy to have everything they needed to get started. It impressed the clients because as soon as they hit accept on the online proposal, Kirk would get notified and he would start reaching out and asking for things. The clients are used to waiting days often after they sign a proposal to like, “When are we going to get started?” We were on it.

Always bring in all the key people that will be in the project and make sure that they're on board. Share on X

We started that engagement with a good impression. I would add to that in terms of separation of duties. It’s not an internal control thing, it’s also a business thing. You have that separate onboarding person, but also have somebody in your firm who is dedicated to sales. A lot of times it’s the owner of the firm doing it or it’s the people providing the accounting services. As with onboarding, you can’t be dedicated to that function if you’re distracted by other things. You can’t be responsive. We had a sales guy, an implementation guy or onboarding guy. We had client services. Those were the three areas of the firm, which freed me up to be able to do marketing, which is how I got into doing the marketing stuff.

What are 1 or 2 other strategies that maybe you learned from this investment place in Santa Monica that could help an accountingpreneur onboard a new client smoother and quickly? Having the cloud software system from desktop go way better and have the clients operate virtually in a way that you found worked well even for your business to get up to 200. A lot of people I’ve been talking to, you probably want to work from home in your jammies. You don’t want to go to the office. You want to get rid of clients coming to your office and wasting your time model. Back in the day, when you were working with those guys in Santa Monica, what are 1 or 2 more strategies that you think would help someone with onboarding a new client?

Making sure that the clients are okay with the virtual model before they sign up is important. If they expect you to always be driving down to Santa Monica, as was the situation for me, it can get very expensive. You’re reminding me that in my contract with them, I didn’t have a provision for travel time. It’s the amateur rookie mistake.

This is good because I call this the costs that we don’t end up charging for. If you talk about pricing or when you’re selling yourself and your services to your clients, how long were you driving all day, Blake, each day?

I live 12 miles from Santa Monica, but it’s an hour at least each way. If I went down to visit, during that project, I was there a few days a week. I was eating 5 to 10 hours easily.

That’s 5 to 10 hours of your time of driving and no compensation for that time.

It’s opportunity costs and fuel costs and all that. I’m not one of those people who says, “Don’t travel.” I think that it’s very difficult to win big clients if you are unwilling to ever go to them. What you do is you incentivize them to let you work remotely. You put in your contract that, “Yes, I will travel, but here are the costs.” There’s a minimum fee for travel time. If I come to visit you, then I’m going to spend half a day so I’m going to bill for half a day even if we only have an hour meeting. You make it more appealing for them to do a Zoom meeting with you. It also helps if you train them on how to use Zoom and we go back to the idea of having an onboarding person who can teach your clients how to use the tools.

AA 41 | Onboarding Clients

Onboarding Clients: It’s very difficult to win big clients if you are unwilling to go to them. What you can do, however, is to incentivize them to let you work remotely.


Don’t expect them to be able to click a link and download the Zoom thing or use Skype without ever having used it before. I teach them how. I never did this, but one of the ideas we had was to give every client an iPad with all of those apps pre-installed. We were never big enough to justify that cost, but as these days, tablets are so cheap. You could invest $500. You could have the clients pay for it. Give them a tablet with your firm’s branding on it that has Zoom. You can call them and they don’t have to deal with tech issues.

That could be a nice welcome gift too for a new client if this is how you truly want to operate. I never even thought of this. This is a good idea, having it have Skype or Zoom. What are some other things if someone wants to steal this idea because it’s a good one? You could do this all year round each month. If it’s January, it’s a Happy New Year gift. If it’s March, it’s Happy Saint Patty’s Day gift. If it’s June, it takes your kids on a trip. Here are all the preloaded apps so you can learn how you’re going to be working with us. What are some other things that you would preload an iPad with if you were to still have this business now? What would you have done differently with those guys in Santa Monica with this little bonus tip?

Maybe not with Santa Monica but I can think of many clients where our big challenge was getting the source documents from them every month so we could do the bookkeeping. Having a preloaded iPad with a scanning app where they could take pictures of the documents that we needed very easily and submit them to us securely, without them having to use their phone or download something. That could be a value add for some of the less tech-savvy people.

Is there a scanning app that you know of that you’d like to share with the audience that is a secure one? I use Doc Scan. I don’t think there’s anything secure about that, but it’s easy for me to send faxes, emails and PDFs.

I use an app called TurboScan, which I like. I originally had to pay for it, but it wasn’t much. That’s a good one. Probably the readers should be investing in some receipt scanning or document scanning app that’s in the marketplace for QuickBooks or Xero. A good example is Hubdoc. AutoEntry is another good one. I’m trying to think of Receipt Bank. Whichever one you use, you install that app on their phone or on this device, then whenever they need to send you something, they take a snap a picture of it and then your team can sort it out in the inbox.

Maybe some of you have thousands of clients. The best way is 80% of your business is going to come from your top 20% of your clients. Even if the top 20% get this preloaded, it’s not only an easy gift, but it makes your life easier. It’s all about onboarding new clients in your accounting firms smoothly so you don’t have any hiccups in the giddy-up.

I’ve got one more tip for you that I can think of off the top of my head and this is my biggest one, which is project management software or some task management software in which to organize all of these onboardings. It doesn’t matter what you use. There’s a lot out there. I used a tool called Podio, which is now owned by Citrix. I used it to build a custom onboarding workflows checklist. It had chat in there. There are lots of collaboration tools like this. If we had done this with the iPad, we would have installed Podio. The clients can communicate security and upload files.

No matter whose fault it is, if a project fails, it’s a failure. Share on X

The number one thing though is making sure that you have project management software with all the tasks. You just copy the project every time you onboard a client so you never miss anything. Share that with them so that they can see the progress. A lot of times working with an accounting firm is like a black box. You don’t know what’s happening or what’s being done. With Podio, we were able to give them a view where they could see here’s where we are in the onboarding and here’s what’s left to happen. They liked that visibility. About half the clients took advantage of logging in to see that.

If I were your client, I would have done that because I’m always in a black box. I’m like, “What’s going on? How come I haven’t heard from you?” This is to change that experience. When people like me become your client, it’s a lot easier.

Back when I had my firm, I used Podio, which is generic project management software because there wasn’t anything specialized for accounting firms. Nowadays there are specialized solutions, so you might want to look at tools like Karbon, Jet Pack Workflow, Client Hub. These are portals/chat tools/task management apps that are designed specifically for accounting firms. You’re doing onboarding by the seat of your pants if you’re not using some checklist.

We don’t ever want to do anything by the seat of our pants because that doesn’t get us anywhere when we wing it. Being able to sell your business and grow it to 200 business clients and now do all this fun other stuff that you love, didn’t happen without having the proper onboarding of these new accounting clients that you learn from your experience with the guys in Santa Monica. Thank you for sharing. Is there anything else you would love to leave the audience with because this was very helpful? It’s always an honor to have you here. I love all these tips.

If you want to hear more from me, check out the Cloud Accounting Podcast. We’re on Apple Podcasts and Google Play. We cover the latest in accounting and technology news every week, so check it out.

Thank you so much, Blake, for being here with us on the show. It is an honor to have you.

Thanks, Michelle. It was my pleasure.

AA 41 | Onboarding Clients

Onboarding Clients: Make sure you have a project management software with all the tasks, and you copy the project every time you onboard a client, so you never miss anything.


What an amazing episode with Blake. There’s so much to learn from his client that went south there on Santa Monica. If you guys are in the LA area, you know exactly where I’m talking about. It is beautiful there, but to drive 12 miles, it took him an hour to do that. That’s pretty crazy. To recap everything that read because I want to make sure that you onboard your clients the right way so you free up more time and you can go do the sales stuff. You need a top-line revenue.

Number one, always bring in the key people. Number two, training for the individuals that are going to possibly be a challenge for you as you onboard a new client. Having training ready to go. Also having someone on your team, someone dedicated to onboarding. Remember who is your Kirk. For him, it was Kirk. Who can you point to have Kirk? If you don’t have a team because you’re a little smaller and you’re just starting out, you could hire a VA for five hours a week to do this. You can create your SOPs in order to do that. Also making sure that you have someone dedicated to onboarding. Having a separation of duties is important. If you’re bringing on a ton of clients, maybe appointing someone on your team for the client relationship department and that’s the experience that they create.

When you have a better experience, you can charge more for it so that means you could increase your prices. The other suggestion, strategy and tip is to make sure the clients are okay with the virtual model. If you are considering or thinking about taking your brick and mortar office into a virtual model, make sure that before you onboard and switch over everything in your firm, that they’re okay with it and they know what the expectations are.

I love his little bonus idea that we snuck in before his biggest number one thing. The bonus idea is to buy some iPads and preload them with apps like Zoom, TurboScan, Skype, Receipt Bank, etc. If you have the budget for it, it shouldn’t cost you more than probably $500 a client. You could charge more and then bake in their cost for you to make that purchase. On Amazon these days, it’s a lot cheaper for an iPad and you can also buy some older iPads that are refurbished for this purpose too. His last tip, which is one of the biggest ones he said, have some task management software. He used Podio. There are others out there.

I want to take a moment and say thank you all so much for joining me and Blake on the show. It’s always an honor to be here. I love talking about this stuff especially if it frees up your time to go make more money and increase your sales. If you have a quick second, please do leave me a written review and a rating on Apple Podcast and subscribe to the show because I love to hear from you. Share with me the one thing that you’ve heard that I said that made a big impact on your firm and you could leave that on a review.

One last thing before I let you go, if you are a little frustrated and stressed trying to get the right referrals and you don’t have any control over who you’re working with or how much you charge or you don’t even believe that you could get a yes from a high paying client, then make sure to check out my Accountants Masterclass over at TheAbundantAccountant.com. You will learn how to feel confident positioning yourself as an expert. Get consistent high-quality referrals from your existing clients and referral partners and get people to say yes to you so you can get paid what you’re worth. Have an amazing day and I’ll see you in the next episode.

Important Links:

About Blake Oliver

AA 41 | Onboarding ClientsBlake Oliver, CPA, specializes in cloud technology and is the co-host of the Cloud Accounting Podcast, which provides weekly news updates for accountants and bookkeepers.

In 2016 and 2017, he was honored to be named to CPA Practice Advisor’s “40 Under 40” list. In 2019, he was named to Accounting Today’s “Top 100 Most Influential People” list.


Love the show? Subscribe, rate, review, and share!

Join the Abundant Accountant Community today:

Pin It on Pinterest

Share This