Head of Business Services

Job Description

Counterpart is an insurtech platform reimagining management and professional liability for the modern workplace. We believe that when businesses lead with clarity and confidence, they become more resilient, more innovative, and better prepared for what’s ahead. That’s why we built the first Agentic Insurance™ system — where advanced AI and deep insurance expertise come together to proactively assess, mitigate, and manage risk. Backed by A rated carriers and trusted by brokers nationwide, our platform helps small businesses grow with confidence. Join us in shaping a smarter future, helping businesses Do More With Less Risk®.

This is a foundational role that requires strong go-to-market instincts, customer-first thinking, and a hands-on approach to building scalable programs. As Head of Business Services, you will own how we acquire, activate, and retain small business customers—from outbound sales and lifecycle marketing to onboarding, support, and partner enablement. You’ll craft and evolve our value proposition, launch multi-channel campaigns, and engage directly with customers and distribution partners to inform strategy and execution. Your work will directly impact how small businesses discover, experience, and stay with Counterpart.

YOU WILL:

• Design & execute a full-funnel acquisition strategy with a strong emphasis on outbound sales & marketing (email, content, product).  
• Craft & evolve clear, compelling value propositions tailored to different small business segments.
• Develop & optimize the customer engagement lifecycle, including onboarding, renewal, & post-claim experiences.
• Leverage direct customer conversations, usage data, & industry insights to shape product strategy, enhance user experience, and refine go-to-market efforts.
• Enable distribution partners to drive growth, through co-marketing initiatives, sales collateral, performance insights, and ongoing training.
• Oversee the customer support experience, with a focus on scaling through partnerships, self-serve automation, and AI.

WE LOOK FOR TEAMMATES WHO ARE:

• Customer-Obsessed – Actively seeks to directly engage and understand small business customers to guide strategy and execution.
• Builders – Thrives in ambiguity, enjoys creating from scratch, and iterates quickly without needing fully defined systems or handoffs.
• Full-Funnel Thinkers – Connects the dots between acquisition, activation, retention, and advocacy — always thinking about the end-to-end customer journey.
• Scrappy – Finds creative ways to make things happen with limited resources, whether that’s bootstrapping a campaign or testing messaging live.
• Experimenters – Uses data to inform decisions, but doesn’t get stuck in analysis; has a strong bias toward launching and learning.
• Collaborative – Comfortable working across Product, Sales, Marketing, and Support to get the full picture and drive aligned execution.

WHO YOU WILL WORK WITH:

• Tanner Hackett, CEO & Founder: Having founded two other major startups, including Button and Lazada, Tanner now spends his time focused on mental health through his philanthropy, Openminded.org, in addition to reading, surfing, yoga, and enjoying the outdoors. 
• Chris Shafer, Chief of Staff: Chris is a published scientific author, having studied the neural correlates of gratitude at the lauded Brain and Creativity Institute. He has since helped to launch numerous businesses in which he held a variety of critical roles from product management to business operations to strategic partnerships. Chris received his bachelor’s degree in Biological Sciences from the University of Southern California.
• Dave Lin, Product Lead: Prior to joining Counterpart, Dave spent the last decade building and scaling products at Yext, Apple, Amazon, and Hookit (a San Diego-based sport sponsorship data analytics startup that was ultimately acquired). He has a MS and a BS in Electrical Engineering from University of California, San Diego. 

We are committed to being a welcoming and inclusive workplace for everyone, and we are intentional about making sure people feel respected, supported and connected at work—regardless of who you are or where you come from. We value and celebrate our differences and we believe being open about who we are allows us to do the best work of our lives.

We are an Equal Opportunity Employer. We do not discriminate against qualified applicants or employees on the basis of race, color, religion, gender identity, sex, sexual preference, sexual identity, pregnancy, national origin, ancestry, citizenship, age, marital status, physical disability, mental disability, medical condition, military status, or any other characteristic protected by federal, state, or local law, rule, or regulation.