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Director of Sales

Remote

Trellis is a profitable, fast-growing Series A startup backed by top investors like General Catalyst, QED, NYCA, and Amex Ventures.

Our mission: make shopping for home and auto insurance faster, smarter, and easier for everyday Americans. Powered by ML and GenAI, we help people find better insurance — saving them time, money, and stress.

We’re fully remote, built for speed, and led by a third-time fintech founder with a track record of building public companies.

If you move fast, take ownership, and care about your craft, you’ll thrive here.

About the Role

We’re looking for a Director of Sales who is both a strong operator and a strategic leader—someone who can turn vision into action while ensuring execution is structured, disciplined, and scalable.

You won’t be doing this alone; you’ll join our existing Sales Directors and management team to lead a growing remote sales organization composed of 4–6 Sales Managers and a team of 50–100 licensed agents focused exclusively on inbound, warm leads. Your mission: scale our revenue engine with precision, build durable systems that keep performance high at scale, and ensure our managers are not just overseeing teams—but actively driving results.

This is a critical leadership role. You’ll be trusted to architect the systems, processes, and team culture that will power our next phase of growth. You’ll be a partner to Recruiting, Training, QA, and Product, and a key driver of Trellis’ consumer business strategy.

What You’ll Own

  • Scale Performance: Drive conversion, productivity, and engagement across a fully remote, high-volume sales org.
  • Lead Leaders: Coach 4–6 Sales Managers to be exceptional at people leadership, performance management, and execution discipline.
  • Build Process: Own the design and improvement of onboarding, coaching, nesting, QA, and intraday management systems.
  • Diagnose and Improve: Identify performance levers using Looker, CRM data, QA insights, and model-driven predictions—then act on them.
  • Drive Execution: Ensure consistent sales operations and tight adherence to processes across teams and managers.
  • Partner Cross-Functionally: Collaborate with Training, QA, Recruiting, and Engineering to launch new initiatives and scale headcount efficiently.
  • Shape Culture: Set the tone for a high-performing, feedback-driven culture built on consistency, clarity, and execution.

What You Bring to the Table

  • 5+ years driving high-performance sales teams, including frontline managers in a high-growth, remote environment, with at least three years of Personal Lines or P&C insurance leadership
  • Strong understanding of insurance carrier dynamics, compliance, agent workflows and best practices
  • Proven success building or scaling distributed teams in a voice driven call center or inside sales tech-enabled environment
  • A strong operator and systems thinker who drives accountability through frameworks and metrics
  • Skilled in sales tooling and analytics platforms (such as Looker, Tableau, ZenDesk, Kustomer, Aircall, TalkDesk, etc.)
  • Comfortable operating in ambiguity—able to define the path while building it
  • Clear, direct communicator who builds alignment across functions and layers

We’re reimagining how insurance is sold—faster, smarter, and built for scale. If you can lead with structure, deliver operational excellence, and build teams that perform consistently, we want to hear from you.

Trellis is a fantastic place to work

Join a talented, passionate team:

  • Flat, collaborative, transparent culture; get in at the ground floor and be a true business partner
  • Opportunities for growth and development within your role and all areas of the organization
  • 75th-percentile (competitive!) compensation
  • 100% remote work environment
  • Quarterly, fun team bonding events

 

Trellis additionally offers competitive benefits:

  • Unlimited vacation time
  • 100% employer-paid Platinum-tier health insurance for employee, 65% for dependents
  • Flexible Spending Accounts (FSAs)
  • 401(k) retirement savings plan
  • Bonuses and equity opportunities
  • Budget for home office equipment

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