Bookkeeper Training Specialist

Do you believe that people learn best when training feels practical, empowering, and rooted in real-world experience

At ClearDesk, we are passionate about helping our Remote Team Members succeed in meaningful careers that support their lives and families. We know that strong bookkeeping training does more than teach systems. It builds confidence, strengthens judgment, and prepares professionals to support real businesses with accuracy and integrity. If you thrive on helping others master technical skills and grow into capable, confident contributors, this role is for you.

Our Story Starts with People Like You

The two founders, best friends, were running businesses that needed great talent fast. So, they started building remote teams across countries like the Philippines, Colombia, and India. Not only did it work, it thrived. They realized that talent isn't limited by geography. With today's technology and high-speed internet, we're able to build high-performing global teams that support businesses across the U.S. So ClearDesk was born.

Today, ClearDesk helps U.S. businesses grow by building world-class remote teams. We don't just connect talent; we manage the entire experience, from recruiting to retention. And while we help clients thrive, we also stay deeply committed to helping our remote team members build real, lasting careers that support their lives and their families.

That's where you come in.

The Role: Bookkeeper Training Specialist

Imagine joining a team where your bookkeeping expertise becomes the bridge between theory and real-world performance.

As a Bookkeeper Training Specialist, you will shape the way our Remote Team Members understand and apply core accounting principles. Our trainees come from diverse professional backgrounds. What they need is structured, practical, and standards-driven training that prepares them to support U.S. clients with confidence.

You will not only teach systems like QuickBooks and Xero. You will guide learners through real bookkeeping scenarios, help them understand financial workflows, and develop the accuracy and attention to detail required in client-facing roles. Through your instruction, coaching, and evaluation, trainees will transition from learners to trusted bookkeeping professionals.

Your work will directly impact client satisfaction, data integrity, and the reputation of ClearDesk. Every session you facilitate and every assessment you conduct contributes to building stronger remote professionals and stronger businesses.

What Your Days Might Look Like:

• Facilitate engaging and comprehensive bookkeeping training sessions for new hires and existing team members
• Conduct live assessments to evaluate bookkeeping knowledge and practical application
• Evaluate and grade trainee performance, providing constructive and actionable feedback
• Develop and update training materials to reflect current bookkeeping standards and software updates
• Create real-world scenarios and exercises covering accounts payable, accounts receivable, reconciliations, and general ledger management
• Audit and review trainee bookkeeping outputs to ensure accuracy and best practice alignment
• Track attendance, progress, and performance while maintaining accurate records in the CRM system
• Generate and analyze trainee scorecards and training dashboards to identify development areas
• Provide one-on-one coaching and respond to trainee inquiries
• Collaborate with the curriculum development team to continuously improve program effectiveness
• Support trainees in transitioning smoothly from training into client-facing bookkeeping roles

Who We Think Will Thrive in This Role:

• You have at least 3 years of professional bookkeeping or accounting experience
• You are proficient in QuickBooks, either Desktop or Online, and ideally familiar with Xero
• You have strong knowledge of accounts payable, accounts receivable, reconciliations, and general ledger processes
• You are comfortable auditing and reviewing others bookkeeping work
• You have delivered training or instructional content to adults and understand how they learn best
• You can break down complex accounting concepts into clear and practical lessons
• You are confident facilitating live virtual sessions and using online collaboration tools
• You are patient, detail-oriented, and able to give constructive feedback
• You are comfortable using CRM systems and tracking performance data
• You are willing to work in a U.S. Eastern Standard Time schedule
• You can secure the required technical setup, including:
• At least a 720p HD webcam
• A noise-canceling headset
• A primary internet connection of at least 25 Mbps
• A backup laptop, backup internet device, and backup power source
• A main computer with at least Intel Core i5 (or equivalent) and 8 GB RAM
• A backup computer with at least Intel Core i3 and 4 GB RAM

Why ClearDesk

Because we believe work should be meaningful, even from home.

At ClearDesk, you'll work with clients who respect your time and value your skills. You'll join a remote-first team that genuinely supports you, and you'll see the impact of your work in real, tangible ways that matter to the people you work with.

We don't just want you to do your job. We want you to grow with us, stay with us, and feel proud of the difference you're making.

Here's what you can expect from us:

• We pay you fairly and on time
• We provide prepaid HMO coverage for your peace of mind
• We help you grow with tools, training, and honest feedback
• We celebrate your wins
• And above all, we actually care

Ready to be part of something that matters

Apply now and start your journey with ClearDesk.

Important Reminder: ClearDesk does not ask for any monetary payments or fees as part of our employment process. If you encounter any request for payment, please disregard it and report it to us immediately. For your security, please ensure that all communications are conducted through emails originating from (@cleardesk.com or @cleardeskteam.com).

Disclaimer: Candidates who apply for this position may be re-profiled to similar roles depending on their qualifications, experience, and current market demand.