The Executive Operations Director is a high-trust, high-impact role designed to maximize the effectiveness of the CEO and Chief Growth Officer by enabling focus, speed, and disciplined execution. As a strategic extension of the CEO, this individual ensures that time, attention, and decision-making are consistently aligned to the company’s highest priorities. Through proactive planning, operational rigor, and strong communication instincts, the EOD creates the conditions for the CEO to lead at altitude — confident that critical workflows, stakeholder coordination, and follow-through are happening with clarity, context, and precision. This role is ideal for a systems-minded operator who thrives in fast-paced, high-growth environments and is energized by making others more effective at scale. Accountabilities: Maximize Executive Leverage + Design and defend executive calendars reflecting strategic priorities + Collaborate with the Executive Assistant team to appropriately manage CEO calendar (schedule meetings, watch for conflicts, prioritize strategic engagements and proactively anticipate needs). + Partner with the EA team to manage all aspects of CEO travel – including flight and hotel arrangements, ground transportation, detailed itineraries and aligned with executive priorities. + Proactively rework time allocation based on board cycles, investor asks, and deal flow + Integrate personal boundaries and recovery time to ensure long-term performance + Ensure executives are aware and prepared for upcoming meetings, etc. + May serve as filter and amplifier for the CEO – triaging communications, surfacing key signals, and ensuring alignment across cross-functional workstreams Business Development Enablement + Draft and manage high-leverage communications in the leader voice, tailored to audience and stage + Anticipate upcoming meetings, events, or outreach opportunities + Track deal-stage-specific needs for materials, prep cycles, or messaging shifts, keeping internal stakeholders aligned and informed + Organize CRM or other shared trackers and files to flag dormant projects, overdue next steps, or open asks from prospects Strategic Leverage & Execution Support + Enable clear and focused meetings by preparing agendas, pre-reads, etc. as appropriate + Ensure decisions and action items are documented, tracked, and followed through to resolution + Help the CEO and exec team stay focused on high leveraged conversations by flagging-low ROI meetings and suggesting streamlining opportunities + Anticipate and prep for high-stakes decisions by organizing inputs, risk, trade-offs, and stakeholder perspectives so the CEO can make decisions efficiently and confidently Board Coordination & Special Projects + Own end-to-end board communications and meeting cadence, including scheduling, material prep, pre-reads, and post-meeting follow-ups + Anticipate and coordinate internal stakeholder input and needs to ensure aligned, timely, and high-quality board communications + Ensure executives are prepped with briefing notes, talking points, etc. + Anticipate and coordinate needs/input/asks from other internal stakeholders + May lead and/or participate in projects to enhance business processes and overall effectiveness + Assist in coordination and tracking for special projects as needed Qualifications: + 10+ years of executive-level support or operations experience, ideally in fast-paced, PE-backed, or growth-stage environments + Experience in P&C insurance organization preferred + Exceptional written and verbal communication + Proven discretion and emotional intelligence + Demonstrated track record of handling confidential and sensitive information with discretion + Strong pattern recognition, critical thinking, and anticipation skills + Executive poise under pressure + Systems thinker who can automate and improve processes Compensation: + $150,000 - $170,000 commensurate with experience, plus bonus eligibility Benefits: We are proud to offer a robust benefits suite that includes: + Competitive base salary plus incentive plans for eligible team members + 401(K) retirement plan that includes a company match of up to 6% of your eligible salary + Free basic life and AD&D, long-term disability and short-term disability insurance + Medical, dental and vision plans to meet your unique healthcare needs + Wellness incentives + Generous time off program that includes personal, holiday and volunteer paid time off + Flexible work schedules and hybrid/remote options for eligible positions + Educational assistance #TMG