1848 Ventures
Remote Jobs
Big challenges. Passionate people. Smart solutions. This is what you’ll find at 1848 Ventures. We help business owners manage uncertainty and discover opportunity in risk. We’re not aiming for incremental improvement – we’re breaking new ground. And when we see opportunity for innovation, we have the freedom, resources, and culture to make it happen. We’re champions of business owners everywhere. After all, it’s this startup ethos and entrepreneurial spirit that 1848 Ventures – and our parent company, Westfield – was founded on. Westfield, a leading provider of commercial insurance, established 1848 Ventures in 2018 to expand beyond conventional property and casualty insurance products and address the broader risks small business owners face every day. We meet our customers where they are, partnering together to deliver digital solutions that improve their bottom line. We know that in order to succeed, we need the right people to make it happen. We start by building a team with a diverse set of voices, backgrounds, and experiences. We’re looking for the innovators. The pioneers. The change agents. The people who aren’t afraid to ask, “What if…?” and try it anyway. This is the place for self-starters, go-getters, and anyone who wants to see a good idea become a great reality. At 1848 Ventures, we help people build careers. Based in Northeast Ohio near Cleveland, our team members grow their creative and commercial skill sets, applying their talents to a wide range of portfolio concepts. And who we are drives what we do – our values empower a thriving culture that allows for true innovation, learning, and growth.
2 Jobs
Otto – Founding GTM Lead
1848 VenturesBig challenges. Passionate people. Smart solutions. This is what you’ll find at 1848 Ventures. We help business owners manage uncertainty and discover opportunity in risk. We’re not aiming for incremental improvement – we’re breaking new ground. And when we see opportunity for innovation, we have the freedom, resources, and culture to make it happen. We’re champions of business owners everywhere. After all, it’s this startup ethos and entrepreneurial spirit that 1848 Ventures – and our parent company, Westfield – was founded on. Westfield, a leading provider of commercial insurance, established 1848 Ventures in 2018 to expand beyond conventional property and casualty insurance products and address the broader risks small business owners face every day. We meet our customers where they are, partnering together to deliver digital solutions that improve their bottom line. We know that in order to succeed, we need the right people to make it happen. We start by building a team with a diverse set of voices, backgrounds, and experiences. We’re looking for the innovators. The pioneers. The change agents. The people who aren’t afraid to ask, “What if…?” and try it anyway. This is the place for self-starters, go-getters, and anyone who wants to see a good idea become a great reality. At 1848 Ventures, we help people build careers. Based in Northeast Ohio near Cleveland, our team members grow their creative and commercial skill sets, applying their talents to a wide range of portfolio concepts. And who we are drives what we do – our values empower a thriving culture that allows for true innovation, learning, and growth.
About Otto Otto is an AI-powered sales platform built for independent commercial insurance producers. We help agencies identify the right prospects, understand risk faster, and match business to the right carriers, all in one product. We're early-stage, growing fast, and looking for our first customer-facing hire to help us scale. The Opportunity Step into a foundational GTM role and own how Otto reaches, converts, and grows a market of thousands of independent commercial insurance agencies across the US. You will work alongside the founding team to drive acquisition, build the GTM playbook from scratch, and ensure the customers you bring in stay and expand. This is a hands-on execution-first role with ownership and direct impact on how Otto grows. What You Will Do Go-to-Market Execution: - Build and execute the Playbook: Own our outbound acquisition strategy; manage and monitor end-to-end campaigns, flag issues, respond to inbound interest, and keep the funnel moving toward revenue. - Drive Conversion: Take prospects from first touch through trial activation, using data and direct customer engagement to improve conversion at every stage. - Iterate Fast: Test and refine messaging, sequencing, and targeting as you learn what resonates with independent insurance agencies. Customer Success: - Own Retention: Guide customers through onboarding and ongoing engagement, keeping accounts healthy and identifying expansion opportunities. - Be the Voice of the Customer: Serve as the primary point of contact for questions, troubleshooting, and escalations, and feed insights back to the product team. Operational Excellence: - Keep the Engine Running: Own CRM in Attio: tracking trial starts, conversions, churn signals, and renewal status across the customer base. - Report with Clarity: Produce clean, actionable reporting on trial conversions, pipeline health, and customer status for biweekly team reviews. Who You Are - GTM Builder: You have 4-6 years of owning GTM execution at an early-stage B2B SaaS or insurtech company, ideally PLG. You've managed GTM elements before, including outbound campaigns, CRM and enrichment tools like Attio or Clay, and know how to move a funnel from zero. You don't wait for a playbook, you write it. - Customer-Obsessed Operator: You understand that GTM doesn't stop at the close. You know how to build trust with customers, turn early adopters into long-term advocates, and spot churn before it happens. - AI-Native: You use AI tools to build workflows around them. You are always looking for ways to do more with less and bring that mindset to everything you touch. - Self-Directed and Adaptable: You thrive in ambiguous, 0-to-1 environments. You will create repeatable playbooks. Familiarity with commercial insurance or fintech is a plus. Why Join Us At Otto, you will have a seat at the table from day one. You will shape how we build the customer function, influence the product, and help define what it means to serve independent insurance agencies in the AI era. This is your chance to co-found something that matters and is backed by a team that moves fast and a market that's ready. Compensation & Benefits - Competitive salary - Remote-first - Direct influence over a category-defining product - Travel up to 25% EQUAL OPPORTUNITY EMPLOYER 1848 Ventures celebrates diversity and is committed to inclusion. All qualified applicants receive consideration for employment without regard to race, color, sex, religion, national origin, age, sexual orientation, gender identity, disability, or status as a protected veteran.
Venture Leader (Otto)
1848 VenturesBig challenges. Passionate people. Smart solutions. This is what you’ll find at 1848 Ventures. We help business owners manage uncertainty and discover opportunity in risk. We’re not aiming for incremental improvement – we’re breaking new ground. And when we see opportunity for innovation, we have the freedom, resources, and culture to make it happen. We’re champions of business owners everywhere. After all, it’s this startup ethos and entrepreneurial spirit that 1848 Ventures – and our parent company, Westfield – was founded on. Westfield, a leading provider of commercial insurance, established 1848 Ventures in 2018 to expand beyond conventional property and casualty insurance products and address the broader risks small business owners face every day. We meet our customers where they are, partnering together to deliver digital solutions that improve their bottom line. We know that in order to succeed, we need the right people to make it happen. We start by building a team with a diverse set of voices, backgrounds, and experiences. We’re looking for the innovators. The pioneers. The change agents. The people who aren’t afraid to ask, “What if…?” and try it anyway. This is the place for self-starters, go-getters, and anyone who wants to see a good idea become a great reality. At 1848 Ventures, we help people build careers. Based in Northeast Ohio near Cleveland, our team members grow their creative and commercial skill sets, applying their talents to a wide range of portfolio concepts. And who we are drives what we do – our values empower a thriving culture that allows for true innovation, learning, and growth.
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 Compensation & Benefits We offer a competitive salary, incentive program, and comprehensive benefits package, aligned to the scope and ownership of the role. EQUAL OPPORTUNITY EMPLOYER 1848 Ventures celebrates diversity and is committed to inclusion. All qualified applicants receive consideration for employment without regard to race, color, sex, religion, national origin, age, sexual orientation, gender identity, disability, or status as a protected veteran.
