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Small Business Specialist - Hybrid

Job in Milton, Ontario, K9T, Canada
Listing for: Small-Books
Full Time, Part Time position
Listed on 2026-10-07
Job specializations:
  • Accounting
    Bookkeeper/ Accounting Clerk
  • Finance & Banking
    Bookkeeper/ Accounting Clerk
Job Description & How to Apply Below

Hybrid (50% remote, 50% in office - Cornwall, ON)

Businesses need to understand their financial performance, but for many smaller ones, this means a trade-off between managing their books and running their businesses. Our mission is to help every business owner thrive, by providing financial insight and peace of mind in one seamless service. Because understanding your finances should be three things: effortless, convenient, and affordable.

We’re growing, and we’re looking for exceptional people to join us on this incredible journey.

What does a Small Business Specialist do?

We named the role a “Small Business Specialist”, because you will be doing more than just bookkeeping. You will be paired with a number of small businesses as their dedicated Small Business Expert (the number of businesses you will support is up to you, whether you would like part‑time or full‑time commitment). You will be tasked with learning their business and investing yourself in their success.

This includes providing ongoing support directly to your chosen number of clients, and performing your duties within the established scope of work to ensure that every client has what they need to effectively run their business. You will be supported by your own dedicated Account Manager, who will help ensure you have the training and tools necessary to confidently perform your best work.

Your Account Manager will also be tasked with maintaining the quality of our data environment, ensuring that the client has the most up to date information to make quality decisions, and when it comes to filing taxes; taking over the file in order to facilitate the year end process.

Over time, the Small Business Specialist will dive deeper into the delivery of the tax services by being responsible for monitoring and facilitating the delivery of our tax services to our clients and by coordinating directly with our Tax Team internally, or with external accountants as needed, in order to do so.

What you'll get up to:
Client Engagement – At the core of everything we do is our clients and their success.

In this role, you’ll be responsible for managing a client portfolio and doing the bookkeeping for these clients on a monthly basis. You’ll be invested in the lives of your clients from various industries — with consistent communication being key to a healthy relationship.

  • Connecting with our clients (via phone, email, and platform) to ensure a timely delivery of their bookkeeping and tax services
  • Helping clients to maintain an accurate tax filing through education and support
  • Use your knowledge of their business to respond to and action inquiries & requests from the business stakeholders, as well as the Tax Team at Small-Books
  • Maintaining accurate and complete bookkeeping records using Quick Books and other cloud accounting software, managing accounts payables and receivables, bank reconciliation, payroll
Take a Stand:

Small-Books is transforming the small business bookkeeping industry by creating a service that prioritizes the success of our clients over anything else. As a Small Business Specialist within the Small-Books team, you are fired up to fundamentally change the lives of our clients through the positive outcomes our team can create. We embrace every setback, conversation, experience, and success as a means of making change happen.

Be accountable to deliver on the Small-Books Team’s quarterly Objectives and Key Results (OKRs) or Key Performance Indicators (KPIs)

Participate in the ideation and systematic improvement process that contribute to us building better systems, tools and processes to deliver superior results for our clients and fellow team members

What you’ll need (soft skills)
  • You must enjoy driving business success through growth,…
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