Head of Sales – 1099 Agent Network
📍 Remote | Full-Time | U.S.-Based
💼 Leadership | Commission-Based Sales Management | Field & Channel Strategy
💰 $250,000 base salary + uncapped commission based on team performance + benefits

About the Role
We are seeking a strategic and results-oriented Head of Sales to lead and scale a national network of over 1,000 independent (1099) sales agents. This senior leadership role is responsible for driving revenue growth through the development and optimization of a high-performing, distributed sales force. You’ll set the strategy, lead field operations, and be accountable for agent recruitment, enablement, and performance across the country.

This is an ideal opportunity for someone who thrives in high-volume sales environments and knows how to drive results through independent contractor networks. The role offers high visibility, executive leadership collaboration, and significant earnings potential through performance-based incentives.

Key Responsibilities

• Lead and Scale: Oversee and grow a large, distributed network of 1099 sales agents across multiple markets

• Recruiting & Retention: Build scalable systems to source, onboard, and retain top-producing agents

• Performance Management: Implement KPIs, dashboards, and incentive programs to maximize agent productivity

• Sales Enablement: Develop training, playbooks, and tools to drive agent success and maintain brand consistency

• Agent Engagement: Foster a high-energy, mission-driven culture that supports agent accountability, communication, and community

• Compliance & Risk: Ensure agent activity meets regulatory and contractual standards for 1099 workforce

• Forecasting & Reporting: Own sales reporting, forecasting, and team performance analytics; provide executive-level insight and strategy

• Cross-Functional Collaboration: Partner with marketing, legal, finance, and product to support sales performance and innovation

What You Bring

• 7+ years of sales leadership experience, with proven success managing 500+ 1099 agents or a large-scale contractor sales force

• Experience in industries such as healthcare, insurance, direct sales, home services, telecom, or gig economy platforms

• A track record of meeting and exceeding revenue targets through channel sales

• Expertise in field enablement, CRM and performance tracking systems

• Strong operational mindset, able to balance people, process, and performance

• Inspirational leadership with a roll-up-your-sleeves approach

• In-depth understanding of 1099 management, compliance, and incentive structures

• Excellent communication, training, and motivation skills for dispersed teams

Preferred Experience

• Experience launching and scaling multi-state or national agent networks

• Familiarity with tools such as Salesforce, HubSpot, or field sales engagement platforms

• Experience in fast-paced startup or hyper-growth environments

Why Join Us?

• Lead and scale one of the largest independent sales networks in the country

• Drive strategy and results in a high-autonomy, high-impact executive role

• Be rewarded with $250,000 base salary + uncapped commission based on team performance

• Strong equity and executive-level benefits package

• Work remotely with national influence and support

Are you ready to take command of a powerhouse 1099 sales team and drive exponential growth? Let’s talk.