Strategic Finance & Compliance Leader

Department: Strategic Finance & Compliance

Company: Breakthrough Strategies, Inc. | BREAKTHRU Multifamily Office

Location: Muskego, WI (Hybrid)

Reports To: Founder/Owner

Locations Supported: Muskego WI, Madison WI, Lexington KY

ABOUT US

Breakthrough Strategies, Inc. is part of the BREAKTHRU family of businesses and multifamily office, with more than 90 teammates across three locations. The organization supports diverse business interests, founding and advisory-client families, and operating companies through financial controls, oversight, and collaboration with entrepreneurial teams.

WHY WORK AT BREAKTHRU

Join a collaborative team where sound financial leadership helps both people and businesses grow. This hands-on position offers the opportunity to develop accounting teams, work directly with the Founder and families, and contribute across financial operations, compliance, investments, and long-term planning in a growing multifamily office.

POSITION SUMMARY

The Strategic Finance & Compliance Leader leads accounting and bookkeeping operations, financial controls, compliance coordination, and finance-related planning across the BREAKTHRU Multifamily Office and its business interests. Reporting directly to the Founder, this role develops people, strengthens standardized work, and maintains accountability for accurate, timely financial operations.

The position includes oversight of accounting for BMFO, Ardent, Xiogenix, and Vendura; month-end close and consolidation at Breakthrough Strategies, Inc.; and coordination of tax, transactional, family advisory, and estate-planning matters with internal teams and external specialists. The role calls for strong judgment, organization, and a willingness to learn across multiple disciplines.

KEY RESPONSIBILITIES

Team Leadership & Accountability

Lead and coach accounting and bookkeeping staff across locations; establish priorities, delegate responsibilities, and review work.

Maintain accountability for quality, deadlines, and the adoption of standardized processes and workflows.

Accounting & Financial Consolidation

Actively manage BMFO accounting through the team and oversee the accounting functions for Ardent, Xiogenix, and Vendura.

Lead month-end close and financial consolidation at Breakthrough Strategies, Inc.

Compliance & Cash Controls

Strengthen approval, verification, reconciliation, and recordkeeping controls over incoming and outgoing funds.

Coordinate Charles Schwab-related workflows with the registered investment adviser (RIA) compliance officer and team.

Tax, Financial Planning & Operations

Coordinate business and family tax planning and preparation with external accountants.

Manage budgets, cash forecasts, banking, lending, insurance, and key performance indicator accountability.

Investment Banking & Transactions

Support buy-side and sell-side mergers and acquisitions, recapitalizations, private investments, and partnerships.

Apply capitalization-table knowledge and coordinate contracts, asset pledges, real estate/1031 exchanges, and aircraft/depreciation matters with specialists.

Family Advisory & Estate Planning

Coordinate estate and gift tax planning support, documentation, and legal correspondence with families, attorneys, and accountants.

Track requests, follow-up items, and deadlines to support timely resolution.

Qualifications

Four-year degree required; ideally five to seven years of accounting experience with operational and tax-planning exposure.

Demonstrated team leadership, strong judgment, organizational skills, and a willingness to learn.

Familiarity with capitalization tables; legal, contract, and compliance exposure is helpful.

Proven organization-wide application of AI, machine learning, and automation to closing the books, reconciliations, and standardized work preferred.

Experience in entrepreneurial, small to mid-sized, or family businesses is valued.

CPA, CFA, Series 7, Series 65, other relevant qualifications, or a law degree are a plus, not required.

Expertise in every specialty is not expected since this role is multi-faceted.

WORK ARRANGEMENT

Muskego-based with hybrid flexibility, supporting the teams and business interests in Muskego and Madison, Wisconsin, and Lexington, Kentucky. This is a salaried position with bonus potential.