Location: Chicago, Miami, Hybrid Office/Remote

The Director of Operations & Integration will be the force multiplier for our COO and Corporate Development team, owning the orchestration of operational integration, program management discipline, and technology-enabled business initiatives. This is a hands-on leadership role for someone who thrives in a fast paced environment, and is committed to operational excellence and aligning stakeholders to drive results.

We’re looking for a delivery assassin — someone who can cut through ambiguity, set a clear path, and bring cross-functional initiatives home on time and on budget.

 

This is a unique opportunity for a highly motivated, entrepreneurial-minded individual to play a pivotal role in a fast-growing, private equity-backed company. With several recent acquisitions, strong revenue and EBITDA growth, and new strategic initiatives on the horizon, the company is scaling rapidly. Backed by a top-tier PE firm, this role offers direct exposure to the C-suite and PE Sponsor, the chance to grow alongside a dynamic, collaborative, and high-performing team.

Key Responsibilities:

Integration & Onboarding

  • Lead integration planning and execution for acquired MGAs and de-novo launches, ensuring smooth onboarding to BSU’s operational, financial, and technology platforms.
  • Own the integration playbook, refining processes to accelerate time-to-synergy while mitigating operational risk.
  • Partner with COO and other executives to align priorities, resources, and timelines.

Program & Project Portfolio Management

  • Build and maintain a centralized program/project portfolio for corporate and cross-functional initiatives.
  • Drive PM discipline — clear charters, milestones, KPIs, and post-implementation reviews.
  • Monitor and manage interdependencies, risks, and resource allocation across initiatives.

 

 

Operational Leadership

  • Drive consensus on functional and technical decisions across major enterprise initiatives, including ERP (NetSuite), Policy Management Systems, and underwriting platforms such as Kalepa.
  • Identify and resolve operational bottlenecks, working with both corporate and OpCo teams to implement scalable, repeatable processes.
  • Serve as the COO’s right hand in operational decision-making and execution readiness.

Tech-Enabled Change (Non-Practitioner)

  • Act as the business-side owner for technology-enabled transformation — translating operational requirements into actionable plans for technical teams.
  • Ensure solution design and adoption align with business goals, operational needs, and ROI expectations.
  • Maintain a working knowledge of systems capabilities and limitations without needing to be a technical builder.

 

Qualifications:

The ideal candidate is high EQ and low ego with strong analytical and problem-solving capabilities.  We seek a candidate that has a relentless execution focus, can influence without direct authority, and uses excellent communication skills to bring clarity and alignment in complex, ambiguous environments.

  • 10+ years in operations, program/project management, or integration leadership, preferably in insurance, financial services, or private equity-backed environments.
  • Proven track record leading integration or large-scale change initiatives with measurable results.
  • Strong portfolio and program management skills, with a disciplined, structured approach to delivery.
  • Deep operational acumen with the ability to translate strategy into execution.
  • Adept at navigating cross-functional decision-making and driving alignment among diverse stakeholders.
  • Prior experience with MGAs, P&C carriers, or insurance adjacent businesses a plus.
  • Prior experience in PE backed, acquisitive business a plus.

 

What we offer:

  • Competitive salary and performance-based bonuses
  • Excellent benefits 
  • 401k program with company match
  • Flexible/Hybrid work environment
  • A collaborative and inclusive work environment 

 

About Bishop Street: Bishop Street Underwriters, a RedBird Capital portfolio company, partners with Managing General Agents (“MGAs”) as well as niche underwriting teams, driving rapid inorganic (acquisitions) and organic (de novo startups) growth across the platform. Bishop Street marries individual business unit’s brand equity with turnkey centralized infrastructure and best-in-class capabilities.