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27 Jan Why ‘Smart’ Accounting Software isn’t as Smart as it Thinks

Posted at 21:43h in Blog by

*An Old-School Accountant’s tongue and cheek take on Why Humans Are Still the Real MVPs of Bookkeeping*

Let me tell you, the first time I saw a bank download in one of those fancy new “smart” accounting systems, I thought, *Wow, this could save me some time.*   Fast forward to the second time, and I’m staring at an expense for “Lunch with a Client” magically categorized as “Office Supplies.” Now, I don’t know what kind of lunches these systems think we’re having, but unless the client is munching on a stapler, we’ve got a problem.

That’s the thing about these so-called “smart” systems—they’re not so smart after all. They’re just guessing! And sure, automation has its perks, but trusting it to handle all your bookkeeping? That’s like letting your toddler drive the family car. Sure, they might get the wheel moving, but you’re going to end up in a ditch.

Let’s talk about why we still need humans keeping the books, shall we?

Automation: The Fool’s Gold of Bookkeeping 
Automation promises you the moon: faster processes, fewer headaches, and perfect categorizations. But let’s be real—it’s more like a moody teenager trying to do chores.
It works half the time and guesses the rest. Here’s what these “smart” systems are really up to behind the scenes: 

1. Playing the Guessing Game
You know what happens when software sees a charge from “Bob’s Repair Services”? It shrugs, flips a coin, and sticks it in “Miscellaneous Expenses.” Maybe it’s repairs; maybe it’s something else entirely. Who knows? Certainly not the algorithm. 

2. Making Rules That Break Rules 
Automation relies on rules, but it can’t adapt when things get tricky. Set a rule for “Tech Solutions Inc.” as “Software Subscriptions,” and guess what? The day you buy a monitor from them, it’s still filed under subscriptions. Why? Because the system doesn’t *think*. 

3. Throwing Context Out the Window
Automation doesn’t know you had a client lunch, hired a freelance designer, or reimbursed your team for travel. It just sees dollar signs and tosses transactions wherever it feels like. Humans? We ask questions and make decisions. Automation just guesses and moves on. 

Why Humans Beat Machines Every Time 
Now let me tell you why us old-school accountants are still the unsung heroes of the financial world. 

1. We Understand the Why
When a charge hits the books, we don’t just slap it somewhere and call it a day. We ask questions: *What is this for? Why does it matter? Where should it go? A human
accountant understands the bigger picture, while automation just files and forgets. 

2. We’re Problem Solvers, Not Guessers
Automation can handle the easy stuff, like matching identical transactions. But when something looks fishy—duplicate charges, unusual activity, or incomplete data—it
doesn’t know what to do. Humans? We step in, fix it, and make sure your books aren’t a hot mess. 

3. Consistency is Our Middle Name
Automation loves to apply rules inconsistently. One month, it’ll categorize “Bob’s Repair Services” correctly, and the next, it’ll toss it somewhere else entirely.  Humans ensure your books stay consistent, which means fewer headaches for you. 

4. We’re Customizable
Every business is unique. Automation doesn’t care if you run a construction company or a cupcake shop; it uses the same cookie-cutter approach. Humans tailor bookkeeping to your industry, your goals, and your quirks. (Yes, we even adjust for your *creative* expense reports.) 

5. We See the Red Flags
Automated systems don’t raise alarms when something looks off. Humans notice when your payroll costs suddenly spike or when your profit margins seem too good to be true.
Machines don’t care—humans do. 

Automation Can’t Do This 
Beyond fixing mistakes, we bring something automation never will: *insight*. A good accountant doesn’t just file your transactions; they help you understand them.  

  • Want to save on taxes?  We’ve got ideas.
  • Wondering where to cut costs? We’ve got answers.
  • Need a strategy for growth?  We’re more than bookkeepers – we’re business partners.

 

Automation is great for repetitive tasks, but it can’t give you advice or build a relationship with you. And let’s face it—your accounting software isn’t going to explain your financials over coffee. (It also doesn’t have a sense of humor, which is a shame, because it sure could use one after all the mistakes it makes.)


The Best of Both Worlds 
Now, don’t get me wrong—technology is a beautiful thing.  I’ll happily use it to speed up data entry and make bank reconciliations smoother. But the real magic happens when you pair automation with human expertise. Let the machines handle the grunt work and let us humans do what we do best: think, analyze, and keep your business on track. 

Let’s Keep Your Books in Shape 
At Siegel Solutions, we’re not just here to fix the mess your “smart” system left behind—we’re here to make sure it doesn’t happen again. With a team of seasoned bookkeepers and just the right touch of tech, we deliver accuracy, insight, and peace of mind. 

If you’re tired of playing guessing games with your finances, give us a call. Trust me—there’s no substitute for the human touch. 

Let’s leave the guessing to Vegas. Contact us today and experience the difference a real accountant makes.

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Kimberly Mitchell
Partner Development Manager

 

Kim is a Partner Development Manager with 10 years of experience working with Strategic Partners. As a 19-year veteran with Intuit and a history of driving growth and sales results within the QuickBooks echo system Kim, brings a wealth of knowledge to our team by assisting us with sales and marketing initiatives while helping us strive for the highest net promoter (clients satisfaction) scores. Kim is passionate about creating and nurturing new partnership opportunities through the relationships she has built over the past 25 years of sales experience.

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Noah

Noah Raney
Senior Account Payroll Manager

 

Noah is our dedicated Intuit Senior Account Payroll Manager who can help you find the right payroll solution for you and your business. He is well versed in all of the QuickBooks platforms being desktop/online/standalone and payroll has been his world since joining Intuit 13 years ago. Whether you are looking for ways to save on time, reduce inflated payroll costs or just get set up with the best discounts, he is here to help. Your success and satisfaction are of utmost importance!

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Sean McCaffery
Global Channel Sales Partnerships and Alliances Leader

 

Sean McCaffery has more than 15 years of experience leading channel sales and cloud solutions in the US and Internationally. Sean has held leadership positions with Avaya in Europe growing the channel business with resellers and distributors in key countries driving double-digit growth. He then joined Rackspace Technology and was instrumental in developing sales growth strategies in cloud adoption for customers and partners. Most recently, he ran channels at Dizzion responsible for dynamically growing and expanding the partner ecosystem through SaaS-based VDI solutions before joining Intuit. Currently, he runs the QuickBooks Solution Provider Program supporting the strong business that solution providers and ISV partners have established as well as finding new opportunities to drive emerging mid-market growth together!

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Gabor Terebesi
Payments Account Manager

 

Gabor Terebesi is an Account Manager with the Payments Team of Intuit for over 15 years. He works in the partner division for Intuit payments to ensure Intuit partners along with any clients of theirs are in the most suitable and financially cost-effective solution accepting payments through eCommerce, QuickBooks, mobile payments, or any other options necessary for their business.

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Aimee Garneau
Accounting Manager

 

Aimee joined Siegel in 2022 as the Accounting Manager overseeing the accounting and bookkeeping team. Aimee brings 18 years of experience with increased responsibility with privately and publicly held companies. Her experience lies with SaaS-based companies as well as in healthcare, consulting, education and nonprofits. Prior to joining Siegel, she held accounting leadership positions with Waban Projects, Elastic Path, Moltin, and Ned Davis Research. Aimee loves partnering with business owners to establish financial reporting and results that promote growth and expansion. When Aimee is not working, she loves spending time with her family and friends and exploring all New England has to offer. She is also an avid Red Sox fan and enjoys going to Fenway Park when she can.

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Jeffrey Siegel
CPA, CEO

Jeff has spent the last twenty years working providing solutions to emerging growth businesses. After graduating from Northeastern University, he spent five years working with two multinational CPA firms in an auditor capacity building a foundation for understanding how business work. He later went on to work in various controller and CFO roles before starting Siegel & Associates (previously Siegel Financial Group) in 2000. In those roles, he sold a company to ADP, raised funds for a major expansion of a large regional IVF clinic, and helped set up accounting and financial structures for dozens of companies. Since starting Siegel & Associates, Jeff has worked with hundreds of clients providing accounting system solutions. Those solutions include setting up QuickBooks in a single-user environment putting in QuickBooks Enterprise in a 30-user environment and integrating various add-ons including inventory, CRM, and e-commerce. He is a Certified Public Accountant, a QuickBooks Pro Advisor, a QuickBooks Advanced Pro Advisor, and an Intuit Solution Provider certified in Enterprise Solutions, Point of Sale & QuickBase. Jeff is also a Microsoft Certified Systems Engineer

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Lori Swartz
Client Support Manager

After graduating from Boston University, Lori spent eight years working in various managerial positions for two national companies. In those positions, Lori developed the skills necessary to manage multiple projects, clients, and resources. She later went on to work for a management company that handled over 25 real estate properties with multiple tenants. Lori joined Siegel Solutions in 2003 as a client services manager where she utilized her skills developed to manage multiple clients and multiple staff. She recently moved into the client support manager role where she is responsible for meeting with and onboarding new clients, managing and maintaining our technology stack along with QuickBooks setups, conversions, training, and consulting.

In her free time, Lori enjoys spending time with her family. She loves to travel, music, and theater.

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Kristin Hogan
Associate

Kristin has been with Siegel Solutions since 2008 when she started as a part-time Office Administrator. In addition to the administrative work for Siegel Solutions, Kristin also assists with bookkeeping for a handful of clients, and manages and processes payroll for about 25 clients. Kristin has been working in administrative roles for many years in various fields, including from an academic department in a local university, a start-up biomedical company, to recording and pricing inventory for a small gift shop. Kristin has also held customer service positions in food service, department stores, a local Boys & Girls Club, and a nursing home.

Outside of work, Kristin enjoys hanging out with family, friends, and the family’s black lab named Clyde. Kristin is a New England Revolution fan and goes to as many games as possible each season.

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Kathy Crouse
Senior Associate

Kathy graduated from Framingham State College. She then attended Bently College in their Accounting Certificate program, while also working as an Assistant Payroll Supervisor and Compensation Specialist in the corporate offices of a large contract employer. After many years of experience as a Full Charge Bookkeeper for a private investment firm, and various small CPA firms, Kathy joined Siegel Solutions in 2001. She enjoys learning about different types of businesses working for Siegel and the satisfaction of tailoring our role to best serve each client's needs.

During her free time, Kathy loves spending time with her family and her dog. She also enjoys DIY projects and exploring the beautiful New England coast.

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Janet

Janet Jodoin
Bookkeeping Associate

Janet joined Siegel Solutions in May of 2022 as an Associate Bookkeeper. In her younger years, while raising her family, she completed her degree in Business and she spent 20 years in the trades as a custom designer. Janet also has 16 years in corporate management. Her strong team support, training, and development led her to support and manage Human Resources. Janet's desire to change careers has led her to return back to bookkeeping at Siegel Solutions. In Janet's free time she enjoys spending time with her growing family. Her personal favorite is creative landscaping in her yard. She also enjoys working alongside her partner in construction and remodeling.

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Tricia

Tricia Gullage
Associate

Tricia Joined Siegel Solutions in 2022 as a bookkeeper and works with our clients to keep their day-to-day bookkeeping in order. Tricia has 12 years of bookkeeping experience working for a large construction company for 10 of those years handling all their accounting and Payroll. She met Jeff our CEO while working there and decided she wanted to join our team.

When not working Tricia enjoys spending time with her family and friends. She recently moved up to the lakes region in NH and loves going to concerts, enjoying her time boating and snowmobiling.

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Ed Jaworski
Professional Services Manager

With over 21 years of corporate experience at PeopleSoft Consulting, Sun Life Financial, and KPMG, Ed brings a big business approach to small business solutions. Prior to joining Siegel Solutions in 2022, Ed helped small businesses get the most out of QuickBooks for 21 years as a co-founder of SMB Partners and the founder of Solutions for Office Software.

Ed is an Advanced Certified QuickBooks® ProAdvisor, a Certified QuickBooks® Point of Sale ProAdvisor, a Certified QuickBooks Enterprise Solutions ProAdvisor, and a Certified SOS Inventory Consultant. Ed holds an MS in Computer Information Systems from Bentley University and a BS in Business Administration from Northeastern University.

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Debby Mono
Firm Administrator

Prior to joining Siegel Solutions in March 2023, Debby had been working in administrative and executive assistant roles for many years in various fields. Her extensive background in these positions has provided her with a range of skills and knowledge that are valuable in her new role as a Virtual Administrative Assistant. She graduated from Suffolk University with a Bachelor's Degree.

Outside of work, Debby can be found at football fields or dojos cheering for her sons. She also enjoys hikes with her dog, Sawyer, reading, sports, and live music. She and her husband also love to entertain family and friends.

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Letitia Cote
Senior Associate

Letitia has an accounting degree and has been working in the Accounting/Bookkeeping industry for over 25 years. Tish is also an Acumatica Business Consultant. Outside of work, Tish has 4 grown children and 5 grandchildren, she loves to ski, hike, bike, and be outdoors. Tish has worked with Jeff for over 10 years.

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Ashley Sumner
Senior Associate

Ashley joined Siegel Solutions in April of 2023 as a Senior Associate. She has worked in accounting for 10 years, working her way up from an associate to a Senior Accountant/Controller at her previous jobs. Ashley loves working with numbers, helping clients out specifically with budgets and financial forecasting. She has an extensive background in Construction Finances including AIA billings, WIP schedules, and financial forecasting public and private construction projections.

When Ashley is not working, she loves spending time with her husband and 2 kids, extended family, and friends and watching her Boston Sports Teams!

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Alison Pickwick
Associate

Alison joined Siegel in 2023 as an Associate. She enjoys producing a product that assists company owners in seeing the big picture of their company. Previously, she put this passion to use as an auditor and as a financial advisor traveling the country to various companies in many different industries. With her passion, she also brings years of experience and vast knowledge to Seigel. After hours Alison doesn't stop working. She gardens, has chickens, teaches her godkids carpentry and small engine mechanics, fishes, makes maple syrup, and even brews her own wines and beers. Whenever she can, she goes to her family camp in northern New Hampshire where you can find her working on a project from planting blueberries to building a shed.

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Andrea

Andrea Alencar
Associate

Andrea graduated from Bridgewater State with a Bachelor's degree in Accounting. Andrea joined Siegel Solutions in 2022. Andrea has gained accounting experience working in various industries including a CPA firm, legal, hospitality, and telecommunications. Before coming to Siegel Solutions Andrea previously worked as a bookkeeper and staff accountant.

Andrea has 4 kids which keep her busy. Outside of work, Andrea enjoys spending time with her kids, being outside, cooking, and going to softball/baseball games.

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Mike Derrico
IT

I started my career in 1983 when I designed and built a device to share a computer program, written by the president of a local bank and his son, running on an Apple Lisa computer. The device allowed the large and expensive Lisa's computer to be shared with bank employees. With this program, and with my device, we started a company to market this unique solution to banks. At this point, computer networks were just starting to be used in businesses. I transitioned my efforts to providing support for migrating banking terminal/mainframe functions to the emerging Personal Computer networking platform. For the next decade, I worked with, and beta tested, numerous technologies to integrate the banking functions from dumb terminals into the now smart desktop computers. After working with a few small consulting firms, I started my own company focusing on providing I.T. support to SMBs. More recently I am now doing the exact opposite by helping customers migrate their PC applications and data from their local computers to The Cloud. A few years ago, I joined Siegel Solutions to add my years of I.T. experience to their firm.

In my spare time, I like to travel, fly my drone and, most importantly, spend time with my family. I also still enjoy tinkering with technology.

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Pat Jaworski
Associate

After spending most of her corporate career in the insurance industry, Pat joined a QuickBooks consulting firm providing bookkeeping services to several small companies. Late in 2022, that firm merged with Siegel Solutions, Inc., bringing Pat and her clients to the group. She provides services to clients in a variety of industries: fitness, construction, beauty, equine care, and medical billing, to name a few. She enjoys supporting her clients by keeping their financial records in good shape and allowing them to focus on growing their respective businesses.

Pat resides in the 495/MetroWest area with her husband Ed, daughter Abby and Duffy, their lovable, energetic golden retriever.

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Noah Tan

Noah Tan

Associate

Noah has over 12 years of experience in accounting and graduated from the University of Bedfordshire in the UK. Prior to joining Siegel Solutions in August 2023, he has worked with clients in Asia and Europe across a variety of industries, including manufacturing, software, e-commerce, and education. Noah specializes in real estate, property management, and construction enterprises.

Noah is a passionate and results-oriented individual with a proven track record of success. He is skilled in financial planning and analysis, budgeting, forecasting, and reporting with expertise in business process improvement and risk management. Noah is committed to helping his clients achieve their financial goals.

Noah loves to travel and has been to over 50 countries and 4 continents with his wife. He is passionate about financial market analysis and enjoys using stock charts to identify trends and patterns.

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Tari Crowley

Administrative Assistant

Tari Crowley joined Siegel Solutions in September 2023 as a part-time Administrative Assistant. She actually wears many hats not just in her position, but in her every day life! She is also a real estate agent, softball coach, wife and full-time mother. When she isn’t busy with everyday life activities, she enjoys spending time with her chocolate lab, Bailey, as well as having fun and laughing with her family.

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DeeAnna Keyes

Sales and Marketing Associate

DeeAnna Keyes, has been our Sales and Marketing Associate since December 2023. She brings a wealth of experience, having worked at Intuit with a focus on Quickbooks Online and Quickbooks Desktop. With a robust sales history and a license as a real estate agent in Virginia, DeeAnna is a versatile professional. Outside of work, she cherishes family moments, indulges in camping with friends, and finds joy in entertaining at home with her husband and four children.

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Janice Kats

Associate

Janice Kats graduated from Carl Sandburg College with an Associate Degree in Accounting in 1992 and has been working in the accounting field ever since in various jobs doing AR, AP, payroll, office management, and bookkeeping before joining Siegel Solutions in late 2023.

In 2022, she made the decision to branch out on her own and started her own bookkeeping business, working from home.

She is a mom to 3 grown children and a grandmother to 5 grandchildren and enjoys spending time with her husband and two dogs and following her grandchildren in all of their sports.

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Roger Hand

Relationship Manager

Roger boasts over 15 years of experience at Intuit, during which he has aided clients and QuickBooks® Solution Providers in building and growing their businesses. He is well versed in the QuickBooks® products and, through the discovery process, knows how we can engage, migrate, and satisfy clients' current frustrations. Roger holds multiple credentials and licenses, including the QuickBooks® Pro Advisor certification. He enjoys working with clients and seeing the satisfaction on their faces when they're achieving their goals without all the confusion! Roger enjoys spending his free time with his wife and two amazing daughters

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Kristina Morin
Senior Associate

Kristina Morin is a Certified Public Accountant from Boston, Massachusetts. She holds an MBA in Management Information Systems from Bentley University and an MS in Accounting and Financial Management from DeVry University. She has been a bookkeeper for 20 years and has spent the last several years teaching QuickBooks and Bookkeeping.

At home, she celebrates her independence, living with her son, father, and two cats, Romeo and Rico. Kristina enjoys old-school hip hop, soaking up the sunshine, and spending quality time watching movies with her family.

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