Paul T O'Reilly And Associates
We don't vet or endorse listed businesses.
Tax Preparation ServicesWatertown, MA
At O’Reilly Strategic Group, Inc., we are proud to carry forward a legacy of excellence in accounting, tax, and advisory services that spans more than five decades. Our roots run deep in the Watertown community, where we have served generations of individuals, families, and businesses under the respected name Paul T. O’Reilly and Associates. In 2025, we embraced a new chapter by rebranding as O’Reilly Strategic Group, Inc., a name that reflects our dedication to innovation, growth, and an expanded range of services. While we look forward under this new identity, we continue to do business as Paul T. O’Reilly and Associates in recognition of the trusted reputation and client relationships that have defined our history since the beginning. Whether you are a long-time client or working with us for the first time, you can rely on the same hallmark qualities that have always set us apart: personalized attention, deep technical expertise, and strategic insight. Today, we combine our longstanding tradition of trust with forward-thinking solutions, helping our clients navigate the complexities of an ever-changing financial landscape with confidence.
Own this business? Claim it free to unlock:
- Manage your photos
- Update hours & business info
Optional
Confirm your Google profile
This step is optional. Find your Google Maps profile, then continue with the normal claim process.
Find on Google MapsOpen your profile, choose Share, and copy the Google Maps link back here.
Ready to manage this business?
Claim This ListingYou might also need:
Frequently Asked Questions
How much does a bookkeeper cost in Watertown?
Freelance bookkeepers: $25–$50/hour. Professional bookkeeping firms: $40–$80/hour. Monthly packages for small businesses: $300–$800/month depending on transaction volume. Payroll add-on: $50–$150/month. Year-end prep: $500–$1,500 one-time. Always ask what's included.
What's the difference between a bookkeeper and an accountant?
Bookkeepers handle daily financial records: data entry, reconciliation, invoicing, payroll. Accountants provide higher-level services: tax strategy, financial statements, CRA audits, business advice. Most small businesses need a bookkeeper year-round and an accountant for tax season.
When should I hire a bookkeeper?
Hire a bookkeeper when: you're spending 5+ hours/month on books, you've missed a tax deadline, your records are behind, you're hiring employees (payroll), or your business revenue exceeds $50K. The cost of a bookkeeper is almost always less than the cost of mistakes.
Do bookkeepers need certification?
No certification is legally required, but look for CPB (Certified Professional Bookkeeper) from the Canadian Institute of Bookkeeping, or QuickBooks ProAdvisor / Xero Certified. These demonstrate training and competency. Always ask about their experience with businesses like yours.
Can a bookkeeper do my taxes?
Bookkeepers can prepare and file simple tax returns (T1, T2, HST/GST). For complex tax situations — corporate restructuring, tax planning, CRA audits, international tax — you need a CPA. Many bookkeepers partner with accountants and can coordinate your year-end seamlessly.