About Feathery

Feathery automates data intake workflows for insurance and wealth management companies. Our customers—including industry leaders like Zurich and Sequoia Financial—use Feathery to power mission-critical workflows such as insurance underwriting, client onboarding, and automated account openings.

Having grown revenue 6x YoY for the past two years, Feathery is rapidly expanding across financial services—and beyond.

Why We’re Looking for You

As demand for Feathery accelerates across financial services and other regulated industries, we’re building out a world-class go-to-market team. We’ve seen exceptional traction with enterprise accounts and are ready to scale up repeatable motion, drive strategic deals, and shape a high-performing sales org.

We’re looking for a Head of Sales to lead this next phase of growth. You’ll own our revenue strategy, grow and lead the sales team, and build the processes that turn product-market fit into scalable, efficient revenue. If you’re an entrepreneurial sales leader who loves building from the ground up, this role is for you.

About the Role

As Head of Sales, you’ll lead Feathery’s go-to-market execution. You’ll define our sales org structure, optimize our motion across inbound and outbound channels, and personally close strategic deals with Fortune 1000 prospects.

You’ll partner closely with the founders and cross-functional teams—product, marketing, customer success—to align on ideal customer profiles, refine messaging, and identify new vertical expansion opportunities.

This is a hands-on leadership role for someone who thrives in startup environments, scales what works, and isn’t afraid to dig into the details while keeping an eye on the big picture.

What You’ll Do

• Own and scale Feathery’s enterprise sales function end-to-end—from pipeline generation to closing and post-sale expansion
• Hire, manage, and coach a growing team of AEs and SDRs
• Create and continuously refine sales playbooks, processes, and forecasting models
• Serve as a strategic partner to the founders and GTM leadership on pricing, packaging, and growth planning
• Identify and lead Feathery’s presence at high-impact in-person events and conferences—both as an attendee and sponsor
• Develop and execute outbound campaigns and field marketing strategies tied to key industry gatherings
• Manage relationships with top-tier prospects and customers, personally leading and closing strategic enterprise deals
• Partner with Product and Marketing to develop ideal customer profiles, messaging, and competitive positioning
• Track and optimize KPIs across the sales funnel—revenue, win rates, cycle time, ACV, etc.
• Build a high-performance, feedback-driven sales culture grounded in integrity, ownership, and results

About You

• 7+ years of B2B SaaS sales experience, including 2+ years managing and scaling enterprise sales teams
• Proven track record of closing complex, multi-stakeholder enterprise deals in the $100k–$1M+ ARR range
• Deep familiarity with field sales strategy—confident leading event-driven sales initiatives and networking in-person
• Willingness to deeply understand the technical details of Feathery's product.
• Strong understanding of the financial services landscape; existing network in insurance, wealth, or banking is a plus
• You combine big-picture GTM strategy with a willingness to roll up your sleeves and execute
• A passion for building—teams, processes, relationships, and a category-defining company