Director, Payroll Regulatory Strategy & Tax Compliance

Who we are

Over 600 employees strong, Asure sees Human Capital Management (HCM) through the lens of entrepreneurs and executives with an owner’s mentality. We help businesses develop their “Human Capital” to get to the next level, stay compliant, and allocate their time, money and technology toward growth. Our HCM platform empowers more than 100,000 clients to build great teams and better manage their people while staying compliant in an ever-changing HR legislative landscape. Asure’s HCM offering includes Payroll & Tax, HR, and Time & Attendance software and HR Services ranging from online compliance tools to a fully outsourced HR department.  

About the Role

Asure Software is seeking a Director, Payroll Regulatory Strategy & Tax Compliance to serve as the connective tissue between our regulatory knowledge, product roadmap, and engineering execution. This is a high-impact individual who can own compliance strategy end-to-end — from monitoring federal, state, and local tax law changes to translating them into scalable product requirements that ship on time and reduce risk for thousands of clients. You'll work directly with Product, Engineering, and Operations leadership to ensure our payroll platform stays ahead of regulatory change — not just compliant, but a competitive differentiator.

What You'll Do

Own the end-to-end lifecycle of regulatory tax changes: intake, research, requirements definition, and production validation

Partner with Product Managers and Engineers to influence roadmap prioritization and define system-level compliance requirements

Lead automation and tooling initiatives that reduce manual compliance workflows and accelerate release timelines

Build and maintain legislative tracking, knowledge management, and compliance release management systems

Serve as the internal authority on U.S. federal, state, and local payroll tax regulations

Provide executive-level analysis and guidance on regulatory impacts to product, operations, and leadership teams

Drive audit readiness and risk mitigation strategies across the payroll platform

Mentor and lead compliance analysts; build team capacity and institutional knowledge

What You Bring

15+ years of payroll tax and compliance experience in an enterprise SaaS or multi-client payroll environment

Deep expertise in federal, state, and local tax regulations with hands-on experience in multi-jurisdiction compliance

Demonstrated ability to partner with Product and Engineering teams as a regulatory subject matter expert

Track record of building operational systems (tracking tools, intake workflows, knowledge repos) that improve team efficiency at scale

Experience with payroll platforms and tax tools such as MasterTax, PTM, Symmetry, BNA, or CCH

Strong analytical skills; able to turn complex legislation and data into clear, actionable requirements

Excellent cross-functional communication — equally effective with engineers, product managers, and executive stakeholders

Bachelor's degree in Accounting, Finance, or related field; PayrollOrg or CPP certification a plus

Why This Role Asure is in an active modernization phase — rebuilding core payroll infrastructure, launching AI-powered capabilities, and scaling our compliance operations to match. This role has direct influence over how our platform handles regulatory change for tens of thousands of employers. You won't be maintaining the status quo — you'll be shaping what comes next.

Compensation

The base salary range for this position is $120,000 - $125,000 based on relevant experience, skills, and industry knowledge.

Benefits

Medical, Dental, Vision, HSA, FSA- All effective on day 1!

Company paid Basic Life Insurance, A+D, Long-Term Disability, and Short-Term Disability

401K Program with 3% safe harbor contribution

Employee Stock Purchase Program

Fitness Reimbursement Program

Self-Managed PTO

Our Mission

To provide Human Capital Management (HCM) software and services that help companies grow, while nurturing a culture of growth around us.

Helping customers grow by getting the most from their human capital.

Helping our employees grow personally and professionally.

Growing relationships in our communities that inspire goodness.

Grow shareholder value

Our Vision

Be the most trusted Human Capital Management resource to entrepreneurs everywhere.

Our Values

Reflect who we are and what we stand for as a company.

Embrace Change

Lead with Integrity

Own the Outcome

Deliver Awesome

Be a Good Human

We are an equal opportunity employer. All candidates must be legally authorized to work in the US, as we are unable to sponsor or transfer Visas at this time. 

NO AGENCIES PLEASE

Any unsolicited resumes sent to Asure Software from a third party, such as an Agency, including unsolicited resumes sent to Asure’s mailing address, fax machine or email address, directly to employees or hiring managers will be considered Asure property. Asure will not pay a fee for any placement resulting from the receipt of an unsolicited resume.