Venture Leader (Otto)

About Otto

Otto is building the AI sales platform for commercial insurance producers.

Independent insurance agencies power a massive, underserved market, but organic growth is broken. Most agencies rely on rate increases, not new business, and new producers struggle to survive in a system that is complex, manual, and slow. It can take nearly three years for a producer to build a viable book of business, and many never get there.

Otto changes that. We turn prospect data, risk intelligence, and carrier appetite into a seamless, end-to-end sales experience so producers can move from prospect to premium faster, with better outcomes and higher close rates. Our platform helps agencies reduce producer failure, shorten learning curves, and unlock sustainable growth.

We launched our closed beta in December 2025 and are already seeing traction across agencies of different sizes. With strong early customer signals and strategic relationships in the insurance ecosystem, Otto is positioned to define the next generation of commercial insurance sales.

The Opportunity

This is a chance to lead and scale an AI-native SaaS business at the center of commercial insurance distribution.

As Venture Leader of Otto, you will own the business end-to-end. That includes go-to-market strategy, revenue growth, product direction, team leadership, and financial performance. You will take Otto from early traction to product-market fit and beyond, with a clear path to scale and profitability.

Otto launches with seed funding in place, giving you the runway to build, learn, and prove traction early. As the business scales, you will lead future capital raises and investor relationships, partnering closely with 1848 Ventures while maintaining full ownership of Otto’s day-to-day leadership and long-term success.

What You’ll Do

• Set the strategy and lead the business: Define Otto’s vision, strategy, and operating priorities. Translate that strategy into clear quarterly and annual OKRs. Own outcomes across growth, retention, customer satisfaction, and financial performance.
  
  
• Build and execute go-to-market: Design, test, and scale Otto’s GTM motion. This includes positioning, pricing, sales strategy, and channel experimentation. You will spend meaningful time in-market with producers and agency leaders, using customer insight and data to refine the value proposition and drive adoption.
  
  
• Demonstrate product-market fit: Lead the team through the iterative work of finding and proving product-market fit. Balance product vision with real-world insurance workflows, carrier dynamics, and producer behavior. Use data to guide decisions and know when to double down or pivot.
  
  
• Build and lead a high-performing team: Recruit, develop, and retain a lean, high-impact team. Set clear expectations, establish operating rhythms, and build a culture of accountability and momentum. You will roll up your sleeves alongside the team, especially in the early stages.
  
  
• Shape the product alongside technical leadership: Partner closely with product and engineering to prioritize features that unlock GTM success. Bring deep sales and market context into product decisions, ensuring Otto delivers real, differentiated value to producers.
  
  
• Align stakeholders and drive decisions: Serve as the connective tissue between Otto, 1848 Ventures, and key external partners. Communicate clearly, build trust, and move decisions forward in a complex ecosystem.

Who You Are

• You are a commercial operator who knows how to build and scale.
  
  
• You have led or played a senior role in an early-stage B2B SaaS business and have taken products from early traction to meaningful revenue. You have deep GTM experience and a strong point of view on how to build, test, and scale sales motions.
  
  
• You understand the insurance industry, ideally commercial insurance. You’ve sold into agencies, carriers, or adjacent services, and you respect the complexity of the space. You know how producers work, why adoption is hard, and what actually changes behavior.
  
  
• You are data-driven but comfortable making decisions with incomplete information. You use metrics to learn quickly, not to hide behind certainty.
  
  
• You are an owner by nature. You take accountability, manage resources carefully, and think long term while executing with urgency.
  
  
• You lead with clarity and empathy. You challenge directly, care personally, and create environments where high performers can do their best work.

Why Join Otto

You will lead a venture tackling one of the biggest unsolved problems in commercial insurance growth. You will have the backing and strategic support of 1848 Ventures, while maintaining real ownership over the business you are building.

This is a rare opportunity to pair deep industry impact with modern AI-driven product development, and to build something producers genuinely rely on to succeed.

Travel

This role is remote. Travel should be expected for customer discovery, relationship building, and team collaboration.

Compensation & Benefits

We offer a competitive salary, incentive program, and comprehensive benefits package, aligned to the scope and ownership of the role.