Payroll Specialist

About HeyDrew

HeyDrew is a new, tech-enabled tax strategy and financial operations platform built for small business owners. We help entrepreneurs reduce their tax burden, build wealth, and run smarter businesses. We're a fast-moving early-stage company that's growing quickly, and we're building out our internal service capabilities to match.

Remote (US Eastern Time Zone is strongly preferred) | Full-time | W-2 | $45,000 - 50,000 base salary/year (DOE)

About the role

The Payroll Specialist will own the execution layer. This role will process payroll on behalf of HeyDrew's small business clients as part of our growing add-on services offering.  You'll work closely with our Tax Valet team and report to the Business Operations Manager.

This is a great role for someone who knows payroll well, works independently, and wants to be part of building something from the ground up rather than maintaining what already exists.

What you'll do

• Build out the SOPs, workflows, and documentation for our payroll service as we scale

• Process multi-entity client payroll regularly (weekly, bi-weekly, semi-monthly, and monthly schedules) 

• Manage onboarding of new clients into the payroll platform, including employee setup, pay schedules, and tax registrations 

• Ensure accurate payroll tax filings across multiple states, including the setup of new state tax accounts 

• Identify and resolve payroll discrepancies quickly and communicate clearly with clients through our Tax Valet team 

• Maintain accurate records, stay current on federal and state payroll compliance requirements, and flag changes proactively 

• Coordinate with bookkeeping, Tax Leads, and Tax Valets to ensure payroll data flows cleanly into each client's financial picture

What we're looking for

• 2 or more years of payroll processing experience managing a high-volume client portfolio; comfort handling 75-100+ client accounts

• 2 years of experience doing payroll for SMB clients

• 2 years of multi-state payroll experience (the more the better)

• 2 years of experience with QuickBooks Payroll required; familiarity with other platforms such as Rippling, Gusto, or Paylocity is a plus

• Working knowledge of federal and state payroll tax compliance, including quarterly and year-end filings

• A proven track record of working successfully in a fully remote environment, managing your own deadlines and workload without close oversight

• Comfortable being the first person in a new position at the company, building out processes and structure where very little currently exists

• Strong attention to detail is required

• Low-drama communication style

Preferred Skills

• Familiarity with platforms such as Rippling, Gusto, Paylocity, etc.

• Experience with multi-state payroll is a plus

• Certified Payroll Professional (CPP) or FPC designation

What we offer

• Up to $50,000 base salary - depending on experience

• 100% remote, full-time W-2 position 

• Medical, dental, and vision benefits (employee-elected) 

• Unlimited PTO 

• Employer-paid life insurance and long-term disability 

• The chance to help build something new, not just maintain the status qur( DOE)DO)(