Bookkeeping and Office Manager

Lifestyle Properties; McMinnville (OR); On-site; USD 45,000 - 62,000; Full time

Benefits offered by this job

401(k)

Company parties

Employee discounts

Paid time off

Training & development

Job summary

Destination Willamette Headquarters – McMinnville, Oregon, is seeking a diligent Bookkeeping & Office Manager to maintain accurate financial records across affiliated businesses and support day-to-day accounting, payroll, HR administration, and general office operations.

The role emphasizes detail-oriented financial work, ownership of tasks, and collaboration with leadership to ensure timely reporting and organized records in a growing hospitality and service organization.

Qualifications

• Minimum of 2 years of professional bookkeeping or accounting support experience.
• Experience maintaining accurate financial records and reconciling accounts.
• Strong understanding of accounts payable, expense categorization, reconciliations, and general bookkeeping practices.
• Strong attention to detail and a high degree of accuracy.
• Ability to manage recurring deadlines and multiple business priorities independently.
• Strong organizational and recordkeeping skills.
• High level of discretion with confidential financial and employee information.
• Strong written and verbal communication skills.
• Proficiency with Google Workspace and related tools.
• Valid driver’s license and ability to meet company driving requirements.

Responsibilities

• Maintain day-to-day bookkeeping records for multiple affiliated businesses.
• Enter, categorize, and reconcile purchases, expenses, accounts payable, and other financial transactions.
• Review invoices and prepare vendor payments in accordance with company procedures.
• Maintain organized supporting documentation for transactions, invoices, receipts, reimbursements, and payments.
• Reconcile bank accounts, credit cards, and other financial accounts.
• Review transactions for accuracy and investigate discrepancies.
• Record and maintain homeowner charges, reimbursements, and other property-related expenses within company systems.
• Assist with homeowner accounting and reporting, including reviewing charges before statements are finalized.
• Track and reconcile expenses and revenue between company entities where applicable.
• Review and process employee mileage, expense reimbursements, and miscellaneous reimbursements.
• Prepare, record, and submit lodging and other applicable taxes according to required schedules.
• Support Pinot Car Wine Tours accounting, including payment reconciliation, driver payouts, gratuities, and related records.
• Monitor outstanding receivables and assist with collection and documentation as needed.
• Assist with month-end and year-end accounting preparation.
• Maintain financial records for CPA, tax preparers, insurance providers, lenders, and partners.
• Assist leadership with financial reporting, research, reconciliations, and projects.
• Help maintain financial controls and identify inconsistencies or opportunities to improve accounting processes.
• Cross-department collaboration; provide administrative support as needed while primarily handling bookkeeping and financial administration.

Skills

Bookkeeping

Accounts payable

Payroll support

HR administration

Attention to detail

Organization

Communication

Google Workspace

Driving

Tools

Google Workspace

Job description

Benefits:

401(k)

Company parties

Employee discounts

Paid time off

Training & development

Bookkeeping and Office Manager

Position Summary

The Bookkeeping & Office Manager is a key member of the administrative team at Destination Willamette and its affiliated companies, including Lifestyle Properties and Pinot Car Wine Tours.

This position is primarily responsible for maintaining accurate, timely, and organized financial records across our businesses and supporting the day-to-day accounting functions that keep our operations running smoothly. The ideal candidate will also have experience supporting payroll, human resources administration, and general office operations.

This is a hands‑on position for someone who enjoys details, takes ownership of their work, and is comfortable working within a growing, fast‑moving hospitality and service organization. The Bookkeeping & Office Manager works closely with company leadership and department managers to ensure financial information is accurate, deadlines are met, records are well maintained, and administrative needs are handled proactively.

While bookkeeping experience is essential, experience with HR, payroll, benefits administration, or employee records is highly desirable.

Essential Responsibilities

Bookkeeping & Accounting

Maintain accurate day-to-day bookkeeping records for multiple affiliated businesses.

Enter, categorize, and reconcile purchases, expenses, accounts payable, and other financial transactions.

Review invoices and prepare vendor payments in accordance with company procedures.

Maintain organized supporting documentation for transactions, invoices, receipts, reimbursements, and payments.

Reconcile bank accounts, credit cards, and other financial accounts.

Review transactions for accuracy and investigate discrepancies.

Record and maintain homeowner charges, reimbursements, and other property‑related expenses within company accounting and property management systems.

Assist with homeowner accounting and reporting, including reviewing charges and supporting documentation before statements are finalized.

Track and reconcile expenses and revenue between company entities when applicable.

Review and process employee mileage, expense reimbursements, and miscellaneous reimbursements.

Prepare, record, and submit lodging and other applicable taxes according to required schedules.

Support Pinot Car Wine Tours accounting, including payment reconciliation, driver payouts, gratuities, and related records.

Monitor outstanding receivables and assist with collection and documentation as needed.

Assist with month‑end and year‑end accounting preparation.

Maintain financial records necessary for our CPA, tax preparers, insurance providers, lenders, and other professional partners.

Assist leadership with financial reporting, research, reconciliations, and other accounting projects as needed.

Help maintain appropriate financial controls and identify inconsistencies or opportunities to improve accounting processes.

Payroll & Human Resources Administration

The amount of responsibility within this area may vary based on the experience of the individual hired.

Maintain accurate employee records and personnel files.

Process and maintain new‑hire, change‑of‑status, and separation documentation.

Enter and maintain employee information within payroll and HR systems.

Review employee timesheets, identify discrepancies, and coordinate corrections with managers before payroll processing.

Support payroll processing and maintain payroll‑related documentation.

Maintain employee reimbursement and payroll deduction records.

Support benefits administration, enrollment documentation, and employee eligibility tracking.

Assist with administration and recordkeeping related to workers' compensation and unemployment claims.

Maintain required employment documentation, including tax forms and other employee records.

Assist with onboarding and offboarding administration.

Track employee milestones, required documentation, and other HR administrative deadlines.

Maintain confidentiality of employee, payroll, and financial information at all times.

Assist leadership with additional HR administration and employee‑related projects based on experience and company needs.

Office & Administrative Management

Help maintain an organized, professional, and efficient headquarters office.

Maintain administrative, vehicle, vendor, insurance, and company records.

Monitor office supplies and coordinate purchasing and replenishment as needed.

Maintain vendor and contractor files, insurance documentation, W‑9s, and other required records.

Assist with company vehicle documentation, registrations, insurance records, and administrative tracking.

Coordinate administrative documentation between departments when necessary.

Assist with employee events, recognition, meetings, and company gatherings.

Support leadership with administrative projects, document organization, reporting, and follow‑up.

Help identify and implement administrative processes that improve accuracy, organization, accountability, and efficiency throughout the company.

Cross‑Department Support

Destination Willamette is a growing hospitality organization, and collaboration between departments is an important part of our culture.

This position may occasionally assist other departments with administrative needs, special projects, guest or homeowner documentation, or operational support. However, the primary responsibility of this position remains bookkeeping, financial administration, and office support.

The Bookkeeping & Office Manager is expected to communicate professionally and collaboratively with leadership, employees, homeowners, vendors, contractors, and other business partners.

Qualifications

Required

Minimum of 2 years of professional bookkeeping or accounting support experience.

Demonstrated experience maintaining accurate financial records and reconciling accounts.

Strong understanding of accounts payable, expense categorization, reconciliations, and general bookkeeping practices.

Strong attention to detail and a high degree of accuracy.

Ability to manage recurring deadlines and multiple business priorities independently.

Strong organizational and recordkeeping skills.

High level of discretion when handling confidential financial and employee information.

Strong written and verbal communication skills.

Comfortable learning and working within multiple software platforms and database systems.

Proficiency with Google Workspace, including Google Drive, Docs, and Sheets.

Self‑motivated with the ability to identify what needs to be completed and follow tasks through to resolution.

Valid driver's license and ability to meet company driving requirements.

Preferred

3+ years of bookkeeping or accounting experience.

Experience supporting multiple companies, departments, or business entities.

Experience with payroll processing or payroll administration.

Experience with HR administration, employee files, onboarding, benefits, workers' compensation, or unemployment claims.

Experience within hospitality, property management, vacation rentals, tourism, or another service‑based business.

Experience working with property management systems or homeowner accounting.

Experience assisting with month‑end reporting or working directly with a CPA or external accountant.

Ideal Candidate

Our ideal candidate is someone who:

Enjoys bookkeeping and takes pride in producing accurate, organized work.

Naturally notices discrepancies and follows through until they understand and resolve them.

Can work independently without requiring continuous direction.

Is comfortable balancing routine accounting responsibilities with unexpected administrative needs.

Understands the importance of deadlines and does not allow important financial tasks to fall through the cracks.

Communicates clearly when information is missing or something does not appear correct.

Is trustworthy and exercises sound judgment with confidential information.

Enjoys creating systems, improving processes, and making an organization more efficient.

Works collaboratively and approaches coworkers with professionalism and positive intent.

Is comfortable working within a growing organization where systems and responsibilities continue to evolve.

Position Details

Position: Bookkeeping & Office Manager

Status: Full‑Time

Classification: To be determined based on position structure and applicable wage and hour requirements

Schedule: Primarily weekday business hours, with occasional flexibility required based on business needs

Location: Destination Willamette Headquarters – McMinnville, Oregon

Reports To: Company Leadership

Work Environment: Primarily office‑based with occasional errands, meetings, or work at other company locations

Success in This Position

Success in this position means that company financial records are current and accurate, accounting deadlines are consistently met, supporting documentation is easy to locate, discrepancies are proactively identified and resolved, payroll and employee records are dependable, and leadership can confidently rely on the information being maintained.

Most importantly, this person becomes a trusted administrative partner who helps bring organization, accuracy, and consistency to a growing company.