Full-Time

Bookkeeper

High Net Worth Accounting Associate

Posted on 8/18/2026

Breakwater Accounting + Advisory

Breakwater Accounting + Advisory

51-200 employees

Outsourced accounting and advisory for SMBs

Compensation Overview

$45k - $55k/yr

+ 401(k) match

Wilmington, DE, USA

Remote

Remote within the United States; ideal candidates are based in Eastern or Central time zones.

Category
Accounting (1)

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Requirements
  • At least one year of accounting and/or bookkeeping experience for high-net-worth families.
  • Familiarity with trusts, estates, and various types of entities.
  • Experience using QuickBooks Online within the last five years.
  • Experience working with multiple sets of books simultaneously, such as bookkeeping for clients with a certified public accounting firm.
  • Ability and willingness to learn new technology and develop resourceful solutions.
  • Organized and detail-oriented working style.
Responsibilities
  • Record and classify financial account activity.
  • Contribute to reconciliations, reporting, accounts payable, accounts receivable, and payroll processing.
  • Submit proper documentation and notes into accounting systems and client records.
  • Assist with onboarding new clients from other service providers and systems.
  • Communicate directly with clients’ family members, vendors, and advisors on a daily basis.
  • Develop expertise in new accounting platforms and software.
Desired Qualifications
  • Candidates are ideally based in the Eastern or Central time zone.
Breakwater Accounting + Advisory

Breakwater Accounting + Advisory

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Breakwater Accounting + Advisory provides outsourced financial services for small- and medium-sized businesses, nonprofits, and private clients. Its offering includes bookkeeping, payroll, and controller services, with a focus on back-office work like accounts payable/receivable, bank reconciliations, and financial reporting. The company uses a technology-forward approach, leveraging cloud accounting tools (notably QuickBooks Online) and a dedicated team of ProAdvisors to deliver customized services. Clients begin with a needs assessment and receive a tailored program, delivered at a flat monthly rate with a one-time setup fee. Breakwater serves multiple industries and also offers a family office service for high-net-worth individuals. In 2021 it was acquired by Cultivate Advisors. The goal is to streamline clients’ financial management and reporting through structured, scalable back-office solutions that support growth and financial clarity.

Company Size

51-200

Company Stage

N/A

Total Funding

N/A

Headquarters

Wilmington, Delaware

Founded

2014

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Simplify Jobs

Simplify's Take

What believers are saying

  • Breakwater still advertises fresh openings in 2026, including AP implementation and accounting roles.
  • Private-client services updated March 13, 2026, show product expansion beyond small-business bookkeeping.
  • Partnering with Cultivate Advisors broadens referral reach across owners, entrepreneurs, and nonprofits.

What critics are saying

  • Dependence on Cultivate Brands since 2021 reduces autonomy and pricing control.
  • Greenhouse showed only one open role in July 2026, signaling uneven hiring momentum.
  • Scale is fragile: one lost founder-client relationship can erode a specialized service firm.

What makes Breakwater Accounting + Advisory unique

  • Lee Podolsky built Breakwater from 2014 to 200-plus clients by 2021.
  • Breakwater’s 2026 private-client offering extends accounting into family office administration and household payroll.
  • Cultivate Brands folded Breakwater into a multi-brand advisory network after October 7, 2021.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

401(k) Company Match

Paid Vacation

Paid Holidays

Hybrid Work Options

Remote Work Options