Marketplace Growth & Sales Operations

Location: Remote (USA, Canada, or LATAM) + International Travel

About the Role

WinIt is at a pivotal inflection point. We are a high-growth, mission-driven platform looking for a seasoned leader to own the engine that powers our expansion. You will be responsible for two critical levers: building and training a high-velocity outbound B2C telemarketing team and managing the "supply side" of our marketplace (our network of legal professionals).

This is a role for a Master Trainer and Builder-Operator. You must be as comfortable designing a sales script and coaching a remote agent as you are diving into the data at 9:00 AM to optimize a conversion funnel.

What You’ll Do

• Build & Train the Team: You won't just "manage" a team; you will build the training curriculum. You will be responsible for the continuous coaching, development, and performance of a remote B2C telemarketing team.


• Scale Remote Operations: Manage and scale high-performing remote teams across multiple time zones, ensuring culture and performance stay consistent.


• Manage Marketplace Supply: Oversee the recruitment, onboarding, and performance of our professional network. You’ll ensure we have the right supply-to-demand ratio to maintain liquidity as we scale.


• Data-Driven Growth: Use your analytical background to build dashboards, track sales funnel conversion, and predict supply needs.


• Global Presence: Occasionally travel to visit our international teams to ensure operational alignment, culture-building, and hands-on training.

Who You Are (Requirements)

• Telemarketing Expert: You have deep experience in the trenches of B2C telemarketing. You know how to handle high-volume dialing environments and script optimization.


• The Coach: You have a proven track record of managing and training B2C sales teams. You know how to take raw talent and turn them into elite agents using structured playbooks.


• The Experience: You have 7–12 years of experience in high-growth B2C environments. You’ve "been there, done that" with scaling a marketplace, but you’re still hungry to be hands-on.


• Remote Management Pro: You are an expert at managing remote teams and understand how to keep people engaged, accountable, and productive without being in the same room.


• Analytical Powerhouse: You are "data-obsessed." You use analytics to find the "why" and can translate data insights into actionable training for your team.


• LegalTech or Marketplace Native: You understand the nuances of a supply-demand business model. Experience in LegalTech, Fintech, or the Gig Economy is a significant advantage.

The "Plus" Factors

• Global Mindset: You are open to international travel. You enjoy visiting teams in different parts of the world to build rapport and drive local performance.