A Q&A with with our very own David Leary

March 19, 2019

With over 20 years of experience, David is a prominent figure within the accounting software industry; providing strategic consultancy to small businesses and accountants on driving business transformation through technology innovation. Before joining AutoEntry, David held a range of roles at Intuit, within customer service, quality assurance, engineering, product development, marketing, and developer relations.

Named one of the "40 under 40" honorees by CPA Practice Advisor, David Leary is also the President and Founder of the Sombrero Apps Company and the Co-Host of the Cloud Accounting Podcast.

David recently joined the AutoEntry team as our principal technology evangelist. As the first interviewee in our new Q&A series, David discusses tech trends, hot topics and what he’s most looking forward to over the next 12 months.


What are some of your highlights from working at Intuit QuickBooks?

DL: It was great to be part of Intuit’s early growth as it matured as an organisation, and to witness its solutions evolve up to the launch of QuickBooks Online. Another highlight was seeing the rapid expansion of the QuickBooks marketplace and the success of so many apps within this ecosystem. As I had the opportunity to work within a variety of departments over the years, I was also able to greatly develop my own skill set.  

What do you love about working at AutoEntry?

DL: AutoEntry is growing quickly, but has retained that ‘startup spirit’, which means there’s a fast paced working environment and a lot of excitement for the future. All wins are celebrated, from securing major new customer accounts, to the arrival of our new coffee machine! I also love that change happens quickly, and that we work together to identify product improvements for the benefit of customers.   

What are your priorities for the year ahead?  

DL: My main priority will be to bring the advantages of using AutoEntry to more users in new locations than ever. I’m a ‘techie’ at heart, so I’ll also be working closely with our CTO and customer success team to make AutoEntry even more dynamic in its capabilities. I guess you could say I’m on a mission to help people “Stop Typing Data”.

Outside of AutoEntry, I’ll continue to co-host the Cloud Accounting Podcast and grow as small business owner for the Sombrero Apps Company.

What technologies will continue to impact accounting software moving forward?

DL: Cloud-based and mobile technologies have already had an enormous impact on business, and they’ll continue to shape how accountants work in the future. Elsewhere, practices have become more adept in automating workflows and connecting apps through what’s known as Application Programming Interfaces (APIs), to reduce manual processes. There’s an abundance of solutions which can integrate into accounting software via APIs to automate everyday activities - whilst giving accountants better visibility into projects and more control of their data. Practices which understand how to leverage these connected solutions and apply these types of technologies, can unlock significant operational benefits and productivity gains.  

For those practices looking to get started with automation, where do they begin?

DL: I think it’s important to take small, gradual steps. Practices right at the beginning can start by automating their emails - creating rules, auto replies and templates to work more efficiently. Then they can automate other time consuming processes, be it onboarding, payroll or bookkeeping data entry. By introducing automation to their practice slowly, accountants will be able to see what method suits them best, without overwhelming their team or taking on too much, too soon.

Is there a ‘recipe’ to effective practice growth?

DL: There are many different paths to success, but I believe that having a niche is key. For practices to scale their business, market their services, provide value to customers and bill them appropriately - accountants need to become an expert in a corner of the market, and “own it”. It’s far more strategic to specialise in a certain area, than attempting to cover all bases and customer types.  

What role does employees and ‘culture’ play in driving forward practice growth?

DL: They play an enormous role. The majority of employees can’t adjust to change, so defining culture early on and hiring the right team, with the right skills, is key. Technology now has a pivotal role within accounting, so firms should take on employees who are able and willing to use automation and the cloud. I’d even suggest that some firms change how they post their open positions, for example, instead of saying “Hiring a Bookkeeper” say “Hiring a Cloud Automation Bookkeeping Expert”. This will filter out the applicants you don’t want, and help you to find the right talent.

What have been some of your most memorable interviews from the Cloud Accounting Podcast’?

DL: We’ve been lucky enough to have had some great guests since launching the podcast, including Geni Whitehouse, Ed Kless, and our own, Brendan Woods, so every episode has been memorable in its own way. A recent highlight was speaking to Matt Paff, who had an interesting perspective on software apps like QuickBooks and Xero, competing at a mid market level when they are paired with the correct suite of apps. He discussed how these suppliers must innovate to retain users, especially as the space gets more crowded with larger vendors seeking a slice of this pie.

Why are industry conferences still so important?   

DL: We spend so much of our day working digitally, but it’s true what they say, technology can’t replace the human touch! Taking the time to attend events in person can be very rewarding, as we see with the likes of QuickBooks Connect. Events like these are so successful, as they represent an opportunity for delegates to expand their professional network, learn from influencers and see live software demonstrations, all in the space of a day. Despite the rise in virtual conferences, I think there’ll always be an appetite for events which offer real value to attendees in exchange for their time.  

What’s the best piece of advice you’ve ever heard?

DL: My good friend, Clayton Oates, once said, ‘Keep giving to the universe and it’ll eventually give back.” This philosophy rang true with me and it’s something I like to live by.

Following your time working within the QuickBooks Apps Marketplace, (and apart from AutoEntry!) which apps should business owners be looking out for this year and why?

DL: There are now hundreds of amazing apps within the QuickBooks marketplace, so it’s hard to choose! However, I think the likes of Veem will be increasingly sought after, as the rise of the gig economy and hourly workers, will mean that instant payments will grow in popularity and necessity.  

As more accountants seek to automate their workflows, practice management tools such as Process Street and Zapier will thrive. And I’ve recently had great success using Canva, Favro, Divvy Virtual Credit Cards, and YubiKeys, which are powerful solutions for graphic design, planning, recurring payments and secure log in.