About Howard Financial

Howard Financial is a full-service back-office solution for companies and entities with bookkeeping, payroll, and bespoke reporting needs that require accuracy, timeliness, and institutional-quality reporting without the burden of full-time staff.

We are an experienced team of bookkeepers and administrators with multiple decades of combined experience across industries allowing companies to focus on their core business while we handle the rest.

Founded in 2023, our team of 90 professionals supports ~40 clients across a diverse range of industries. We recently reached $5M of contracted ARR and are growing rapidly (over 150% MRR growth YTD).

We are hiring a highly detail-oriented Sales Tax Specialist to own sales tax compliance for Howard’s vacation rental clients. This role is responsible for managing sales tax, room tax, occupancy tax, and lodging tax filings across dozens of state and local jurisdictions, ensuring filings are accurate, timely, and fully supported by underlying reservation and trust accounting data.

The ideal candidate is methodical, skeptical of numbers until proven, and comfortable operating in a high-volume, multi-entity environment. You should enjoy reconciling messy data, navigating jurisdiction-level rules, and holding both internal teams and clients accountable for clean inputs.

This is an execution-heavy role with real ownership over outcomes—not a review-only position.

What You’ll Do:

 Prepare, review, and file sales tax, room tax, occupancy tax, and lodging tax returns across state, county, and

municipal jurisdictions for multiple vacation rental clients

 Reconcile tax filings to PMS data (e.g., reservations, fees, cleaning, channel commissions) and trust accounts

 Validate taxable vs. non-taxable revenue classifications by jurisdiction

 Track jurisdiction-specific filing frequencies, deadlines, and rule changes

 Maintain accurate tax calendars and filing schedules across all assigned clients

 Coordinate registrations, nexus analysis, and jurisdiction onboarding for new markets

 Identify discrepancies between PMS data, GLs, and tax reports—and chase resolution

 Work closely with accounting, trust accounting, and operations teams to ensure clean upstream data

 Respond to client questions regarding tax treatment, filings, and notices

 Assist with tax notices, inquiries, and audits when they arise

 Maintain clean documentation and audit trails supporting all filings

Ideal Candidate:

 2–5+ years of experience in sales tax / indirect tax, preferably in hospitality, vacation rentals, or lodging

 Strong understanding of room tax, occupancy tax, and short-term rental tax structures

 Comfortable working with high-volume transactional data

 Extremely detail-oriented; reconciliation issues bother you until resolved

 Strong organizational skills and comfort managing dozens of concurrent deadlines

 Confident chasing missing data and pushing back on incomplete or inaccurate inputs

 Able to work independently with minimal hand-holding

 Clear written and verbal communicator

 Comfortable operating in a fast-growing, imperfect environment

Nice to Have (Not Required):

 Experience working with PMS systems (e.g., Streamline, Guesty, Hostaway, Track, Escapia)

 Exposure to trust accounting or client funds segregation

 Experience with Avalara, Returns software, or jurisdiction portals

 Prior experience supporting institutional or PE-backed clients

Why Howard?

 Work on complex, real-world tax problems—not theoretical compliance

 Own outcomes end-to-end with real accountability

 Be part of a rapidly scaling platform serving sophisticated clients

 Clear expectations, clean scopes, and a culture of “done means done”

 Opportunity to grow into senior tax leadership as the tax function scales