How We Sell - Damien Greathead, VP North American Sales, ReceiptBank

How We Sell – Damien Greathead, VP North American Sales, ReceiptBank

By Steve Woods in #HowWeSell

I had the pleasure of speaking with Damien Greathead, VP of North American Sales, ReceiptBank recently.  Damien manages a go-to-market strategy that maintains an interesting dynamic between accountants and the businesses they serve.  In doing so, he and his team deliver a great pre-accounting product that enhances the lives of anyone who works with the expense process (full disclosure – Nudge is a happy customer of ReceiptBank).

I hope you’ll enjoy the conversation as much as I did!


Damien, perhaps we can start off with a little bit about ReceiptBank.  For those who are not familiar with ReceiptBank, what is the offering?

ReceiptBank is a pre-accounting tool. And so that begs the question ‘what is pre accounting?’. Our objective is to help business owners and the accountants who serve those business owners be much more efficient in their bookkeeping and accounting processes.  ReceiptBank, ultimately, collects, organizes, and prepares all of the information associated with the clients’ bookkeeping function. It prepares that information for the accountants review.

That’s a combination of the bank statements, receipts, supplier invoices, credit notes, check images and so on. We want to eliminate all the time associated with collecting and organizing that information. We automate that and then prepare it for the accountants’ review. We take care of the data entry through OCR data extraction that takes care of recognizing the name of the supplier, invoice number, amount, taxes such as GST or HST in Canada.

We take care of all of that data entry and then machine learning kicks in.  Our machine learning remembers how we categorized Hilton Hotels, how we categorized Uber, etc. So it takes a lot of the manual work associated with bookkeeping and accounting out of the hands of accountants and bookkeepers, which frees them up to do much more valuable activities. So in a nutshell, we want to save about 50% of an accountant bookkeepers time in getting all of that information ready for the general ledger.


That’s interesting because it’s not the first time that I’ve heard this concept; you mentioned a lot of AI under the hood, but it’s not flying cars and talking robots. You’re focused on elevating the person doing the business function by using AI to do all of the grunt work. So what happens to those bookkeepers and accountants when they’re not distracted by manual entry?

Approximately 50% of the time spent on bookkeeping is on the routine and the mundane – the activities that can be automated. It’s the other 50% of their time that truly adds value. That’s where accountants are looking for anomalies, digging deeper into the reports, looking at budget versus actual, and thinking strategically about what these numbers mean.  If we can take care of the heavy lifting that will free up time for the accountants to look more closely at the numbers and identify opportunities for improvement.

We allow accountants and bookkeepers to either spend more time with their best clients or get out and win new clients, but ultimately it is about those more valuable activities, which I think is where the true value of accountants and bookkeepers is.


Let’s shift gears and look at this from a go-to-market perspective. How does somebody who has never heard of ReceiptBank discover the concept? How do they how do they come across you? How do they start learning about what it is that you offer?

There are a couple of strategies that we’ve pursued.  First and foremost is working with the associations and the membership groups that accountants and bookkeepers are a part of. Accounting bodies such as the AICPA, State accountancy bodies, the Intuit Pro advisor program, and the Xero advisor marketplace.  These places are where the accountants and bookkeepers congregate and go to for their information.

We’re going to hang out where accountants and bookkeepers hang out.  That’s where we focus our time and time and attention to drive people to ReceiptBank and then into our into our accountants program or our free trial.


Let’s drill in a little bit on that.  I think you used the phrase “we hang out there”. What does that mean specifically? How do you engage with these audiences, tactically, from a go to market perspective?

It’s sort of a catch-all. It’s answering general ledger questions, engaging with people, and just being generally helpful.  We’re always at the user conferences for the major accounting packages like Intuit and Xero. At those events, we have education not just around ReceiptBank, but more importantly how ReceiptBank fits into the workflow of an accounting firm or of an accounting department in a small business.

We work with our strategic partners and have a presence at their association meetings. We focus on being helpful and sharing the best practices we’ve learned through our work with more than 200,000 businesses around the world. We’ve learnt a lot of mistakes and we’ve seen how different firms have implemented the technology. We share a lot of those best practices in our education programs and we work to help different segments of the market from small start-up accounting firms or small start-up businesses.

Wherever they hang out, we’re looking to see where we can be helpful with our education, our best practices, and with feedback on industry trends.


You’ve mentioned a really interesting dynamic that ‘d love to have you comment on.  You have accounting firms and you have business owners and each one may then bring in the other in a virtuous cycle. How does that virtuous cycle help drive awareness of ReceiptBank, and your growth?

You’re right, it’s an interesting cycle.  In many situations we’re coming top down and helping accountants identify what they should be talking about with the business owners they serve.

We’re also helping educate small business owners about ways in which they can be more efficient in their own back office processes. So whether it’s the accounting firm talking to the business client or the business client talking to the accountant, the key thing is to spark a conversation about how to make their manual work more efficient.  

When we first engage, the business owner and their team might be doing it all or the accounting firm might be doing it all.  More often than not, it’s somewhere in the middle. Really what we’re trying to do is to educate both the accountants and their clients about how they can be more efficient in their back office processes.  So, for us, it’s both a top-down and a grassroots approach.


It’s an interesting balance.  What were some of the learnings along the way where you thought a strategy should work and it turned out not to work?

It sounds a bit ridiculous saying it now but one major learning for us was that all accountants are not equal. It’s a mistake to treat accountants or business owners as a homogeneous group.

We’ve recognized that whether it’s technology adoption or our service offering, we’ve got to treat different segments of the market differently.  It’s simple to think that an accountant is an accountant or a business is a business, but that’s too simplistic of an approach. What we’ve realized is that different sized firms and different sized businesses have different challenges.

They have different hopes and dreams and if we don’t tailor our message to the hopes and dreams of that particular segment, then we’re going to fall on deaf ears.


Excellent. Let’s move on to the free trial.  A lot of this effort you’ve mentioned is driving people towards a free trial process.  I’d love to hear your perspective on that as I know that many other sales leaders are wrestling with how a free trial process fits into their go-to-market process.

I think one of our key learnings was that just because someone’s taken out a trial doesn’t mean they’re ready for a phone call. Mapping the client journey was critically important for us.  Identifying when, exactly, are they ready for a call and then how do we get to them?

How do we automate getting them ready for that call through product enhancements, product messaging, and nurture messaging?  Because ReceiptBank integrates into the general ledger, that was a key inflection point. If they’re taking that step to integrate ReceiptBank into the general ledger then we’ve got them a certain distance down journey and that means that they’re almost ready for a call.

We call to find out more about their business – what they’re trying to achieve.  We found that if we were able to isolate or identify the particular inflection point, it saved us enormous amount of time as compared to just chasing everyone that downloaded the free trial.

So for any other sales leaders with a free trial process, I would definitely recommend putting the effort in to find that inflection point where it’s gone beyond the benefit of “free” to actually seeing if your product delivers on what it’s promising.  Resources are limited. You can’t call everybody that takes a trial. How do you set yourselves up for success? The key to that is identifying when people are ready. It’s not simple to find, but I can guarantee it’s not 30 seconds after they’ve started a trial.


Tell me about the person on your team who makes that call it. It feels like you’ve got a fascinating mix of skills there; from classic selling methodologies all the way through to customer success approaches.

Let’s backtrack a little bit.  We have – I’ll call them two channels – one is our accountants channel and one is our business owner channel.  That in itself requires two quite different people, two quite different workflows, and two quite different processes.

What are the what are the skill sets of those people? They’re quite different in our accountants channel. It’s a much longer and much more in-depth relationship. We’re going to be with this accounting firm for a long period of time because they will be talking about ReceiptBank to more and more of their clients. Our team is set up to support an accounting firm that then supports hundreds of their clients.

That type of person is quite different to those who work with the direct business owners where we’ve got to use automated means to get them down the sales funnel to a certain point before we use resources for outreach.


Let’s shift gears to measurement and metrics.  That’s another topic that high-performance sales leaders think deeply about.  You’ve mentioned limited resources a few times, which I think is a common scenario. What do you focus on measuring in your sales organization?

I work backwards.  One of the most important elements that we measure – as it’s tightly correlated to success – is daily active users.  We measure that by number of submissions to ReceiptBank. Businesses are incurring expenses on a daily basis, so there’s no reason why a business shouldn’t be using our app every day.

We’ll look at how many clients of an accounting or bookkeeping firm are using it on a day-to-day basis and how much information they are submitting.  That’s a key element of the customer success journey that we’re very focused on measuring.

For sales, again recognizing that not every customer is created equal, we look at how we spend our time.  We want to make sure that we’re spending the right amount of time with the with the appropriate segment. Obviously we’re looking at the monthly recurring revenue generated by our team as well as the expansion revenue within that team.

From those metrics, you can see how team members are spending their time and how successful that is based on the revenue that they’re generating.  This helps us work with our sales team on a daily, weekly, and monthly basis to make sure that they are managing their time appropriately and optimizing revenue accordingly.


Damien, many of our audience members are sales leaders, but many of them are also aspiring sales leaders.  They are looking at their careers and planning out a path to sales leadership. What advice would you give them on how best to head towards a leadership role?

Understand what really drives the business.  Understand what really drives the success of the sales team. Is it revenue? Is it just new logos, or new dollars of revenue (and why)?  What is it that really drives the success of the business.

What are the different aspects of a sale? What are the nuances between the different segments within the marketplace?

It’s easy just to follow the leader and just crank out the calls.  You certainly need to get into that habit and get those ten calls out before 10:00 in the morning or whatever the strategy is.  But, as you start to develop that habit, look at what’s driving your success and think about how you efficiently get to, and exceed your target.

That comes from working with more senior sales people and looking at what they do and asking them questions about their process.  If you can understand how to efficiently drive sales in your own domain, then you’ll be able to share those skills. How can you drive those same activities throughout the team?


Thank you for joining us today Damien. We really appreciate your insights!


This conversation is also available as a podcast on all your favourite streaming platforms.  Click here for the audio version.


Steve Woods
CTO and Co-Founder
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