Otto – Founding GTM Lead

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%