Chief of Staff, Adaptive

Montauk Capital • Austin, TX

28d • Onsite

About The Position

Adaptive is looking for a Chief of Staff who thrives at the intersection of strategy, operations, and execution. We are a scrappy start-up with everyone very hands-on - you will be too. This new role sits at the right hand of the CEO and touches every part of the company. As Chief of Staff, you will be a true Jack or Jill of all trades: one day preparing board materials and sitting in on strategic partnership conversations, the next diving into agent operations or helping unblock a product launch. You will serve as a force multiplier for the CEO and leadership team, ensuring that high-priority initiatives move forward and that nothing falls through the cracks. If you love solving a wide variety of challenges, operating with autonomy, and helping early-stage companies scale, this role is for you.

Requirements

• 5+ years of experience in strategy, operations, or similar roles (consulting, business operations, chief of staff, or high-growth startup experience strongly preferred)
• Leadership presence: Comfortable interacting with executives, investors, and external partners, and capable of representing the CEO with confidence
• Analytical mindset: Capable of digging into data, extracting insights, and translating those into clear, actionable recommendations
• Technical fluency: Can work effectively with engineering teams, understand technical constraints, and communicate product requirements clearly
• Operational excellence: Experience managing complex, multi-stakeholder processes with rigor and accountability
• Self-starter mentality: You don’t wait for direction; you identify problems and solve them
• Strong communication skills: Can explain complex topics clearly to both technical and non-technical audiences

Nice To Haves

• MBA or equivalent advanced degree
• Background with insurtech, fintech, or B2B SaaS
• SQL or basic data analysis skills
• Experience working with a small team in a high-growth environment

Responsibilities

• Act as an extension of the CEO: prepare materials for board meetings, investor updates, and key external conversations
• Represent and stand in for the CEO at internal and external meetings, with the credibility and presence to do so effectively
• Drive high-priority cross-functional initiatives from idea to execution, keeping the business moving and the team aligned
• Synthesize information from across the business to surface insights and support strategic decision-making
• Own key operational processes across functions including agency/MGA operations, financial reporting and analytics, and product - rolling up your sleeves wherever the business needs you most
• Build and maintain dashboards, processes, and documentation that create leverage and scale with the company
• Identify and eliminate operational friction points across the business, coordinating between engineering, distribution, marketing, and external partners
• Manage and resolve day-to-day operational issues with speed and good judgment
• Collaborate with engineering and distribution to identify opportunities to improve our quoting platform and customer experience
• Translate data and user behavior into clear, prioritized recommendations for the team
• Manage compliance submissions and SLA tracking for products sold

Benefits

• Competitive salary and equity: You’ll have a real stake in what we’re building
• Direct impact: Your work directly affects every facet of our company and our growth
• Learning and growth: Exposure to all aspects of building a business, from product to operations to strategy
• Autonomy and ownership: We hire smart people and trust them to do great work
• Additional benefits: 401(k), Company paid benefits, PTO, and so on

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed