Director Of Insurance Operations Jobs in Milwaukee, WI

Heavy Civil Construction | Southeastern Wisconsin

A well-established Milwaukee based, family-owned Heavy Civil Contractor is seeking an experienced Director of Operations to join its executive leadership team. This is a confidential succession opportunity created by the planned retirement of a longtime operational leader.

The selected individual will serve as a trusted partner to the company president, provide leadership across multiple operating divisions, and help guide the organization through its next stage of growth. Depending on experience and organizational fit, the position may initially be structured as a General Manager or senior operations role before progressing into the Director of Operations title.

The company is a respected, multigenerational contractor with a long history of successfully completing complex public- and private-sector construction projects. Its capabilities include:

• Heavy civil construction

• Underground utilities

• Concrete construction

• Earthwork and grading

• Concrete crushing and material processing

• DOT and municipal infrastructure

• Data centers and power plants

• Airport construction

• Private-sector site development

Although the organization has grown substantially, it continues to operate with the accessibility, flexibility, and personal relationships of a family-owned business. Ownership is visible and engaged, senior leaders are trusted to make decisions, and unnecessary corporate bureaucracy is kept to a minimum.

The Director of Operations / General Manager will work closely with the president and senior project leadership to support company-wide operations, solve complex challenges, and strengthen the organization’s ability to grow.

This position is not designed to micromanage an experienced project management team. The successful candidate will build credibility, earn trust, and become a valued operational resource to ownership, project managers, field leaders, and employees.

The role requires a leader who can think strategically while remaining close to the work. The right individual will be equally comfortable discussing company growth with ownership, helping a project team resolve an operational challenge, evaluating equipment needs, addressing a safety concern, or strengthening an important customer relationship.

• Serve as a trusted operational partner and advisor to company ownership.

• Help develop and execute strategies supporting continued, sustainable growth.

• Provide leadership across concrete, underground utilities, earthwork, grading, crushing, and related operations.

• Support project managers and field leaders with complex project and operational challenges.

• Address company-wide matters involving safety, OSHA compliance, personnel, equipment, scheduling, and field operations.

• Assist with equipment purchasing, trade-ins, fleet utilization, and long-term capital planning.

• Monitor operational performance and identify opportunities to improve efficiency, profitability, and accountability.

• Support multiple affiliated business entities, facilities, and company-owned properties.

• Maintain strong relationships with customers, employees, subcontractors, vendors, industry partners, and community stakeholders.

• Take ownership of operational responsibilities that cannot sustainably remain with the president.

• Preserve the autonomy of experienced project leaders while providing guidance, resources, and accountability.

• Help strengthen the company’s systems and processes without compromising its entrepreneurial, relationship-driven culture.

• Senior operational or executive leadership experience within heavy civil construction.

• Demonstrated success growing a construction company, division, regional operation, or operating group.

• Strong technical and operational knowledge in at least one of the following areas:

  • Concrete construction

  • Underground utilities

  • Earthwork and grading

  • Crushing and material processing

  • DOT or municipal infrastructure

• Broad exposure across multiple heavy civil construction disciplines is strongly preferred.

• Working knowledge of construction equipment, fleet management, utilization, and capital purchasing.

• Experience managing safety, OSHA, personnel, and field-related challenges.

• Strong financial and operational judgment.

• Excellent communication, problem-solving, and relationship-building skills.

• Ability to earn the confidence of experienced, independent project managers and field leaders.

• Collaborative leadership style with a focus on trust, accountability, and shared success.

• Willingness to remain hands-on and become involved wherever leadership is needed.

• Ability to professionally represent the organization throughout the construction industry and local community.

The ideal candidate is a confident but approachable leader who understands that influence must be earned. This individual will enter the organization ready to listen, learn, build relationships, and understand the company’s existing strengths before making significant changes.

Candidates coming from large contractors are encouraged to apply but must be comfortable operating in a hands-on, family-owned environment. The successful leader will not rely on layers of corporate support and must be willing to roll up their sleeves, solve problems, and work directly with ownership, project teams, and field personnel.

This opportunity is best suited for someone who:

• Values autonomy but also understands accountability.

• Leads through credibility, communication, and collaboration.

• Can balance strategic planning with day-to-day operational involvement.

• Respects the knowledge of experienced project and field leaders.

• Wants to make a long-term impact within a stable, growing organization.

• Is interested in becoming a trusted member of an established leadership team.

• Starting base salary of approximately $200,000.

• Final compensation will be based on experience, qualifications, and the eventual scope of the position.

• Relocation assistance may be available for an exceptional candidate.

• Additional details regarding the overall compensation package will be discussed during the interview process.

This is a rare chance to join a stable, respected heavy civil contractor during an important leadership transition. The selected candidate will have direct access to ownership, meaningful authority, and the opportunity to influence the company’s long-term direction without navigating excessive corporate bureaucracy.

The organization offers a strong foundation, an experienced project management team, a diverse project portfolio, and a culture built around trust, independence, accountability, and long-term relationships.

Qualified candidates are encouraged to apply for a confidential conversation. All inquiries and applications will be handled with discretion.