Sales Team Leader

HelpGrid is a performance-driven growth partner for eCommerce brands in the health and wellness space. We specialize in abandoned cart recovery, post-sale engagement, and customer support. Helping our clients recover 10–15% more revenue from existing traffic. In fact, our work drove over $35 million in additional revenue for our clients last year alone. We’re selective about who we work with, and we only get paid when we deliver results.

What started as a small but mighty support team has grown into a full-scale revenue engine, and now, a tech company. We've built custom internal tools to optimize conversations, scale faster, and deepen customer connection, and we're now turning those tools into software products powered by AI and automation.

Whether you're a closer, a creative, a builder, or a systems thinker, there's room to grow with us. We care about performance, but we care just as much about people, and we’re building a place where both can thrive.

We’re growing fast, and we’re looking for people who want to grow with us.

Main Responsibilities

The Outbound Sales Team Leader & Sales Performance Coach is responsible for leading, motivating, and developing the Outbound Sales Team to exceed sales targets while providing targeted coaching, training, and strategic support. This role blends leadership with hands-on performance coaching to enhance agents’ ability to overcome objections, upsell, upgrade, and cross-sell—ultimately increasing revenue, AOV, and customer satisfaction.

Key Responsibilities

Sales Leadership & Team Management

• Lead and inspire a team of outbound sales representatives to deliver excellent performance and meet/exceed KPIs.
• Create and maintain a motivating, collaborative, and fun team environment.
• Manage day-to-day operations, prioritizing tasks, and making impact/risk assessments to achieve SLAs.
• Oversee attendance, retention, and adherence to company policies, applying performance management consistently when necessary.
• Support the team by taking live calls when required, especially for new offers.
• Ensure up-to-date knowledge of products, promotions, and processes, and cascade this to the team effectively.

Sales Performance Coaching & Training

• Conduct regular one-on-one and group coaching sessions to improve sales skills.
• Develop and deliver training materials on overcoming objections, upselling, cross-selling, and handling challenging customer interactions.
• Provide real-time feedback during calls, leveraging role-play and mock calls to reinforce best practices.
• Monitor call quality, listen to recordings, and provide actionable performance feedback.
• Identify trends in objections and develop effective counter-strategies.
• Performance Analysis & Strategy Development
• Track and analyze key sales metrics to identify performance gaps and training needs.
• Collaborate with management to create personalized coaching and development plans.
• Suggest and implement process improvements to enhance sales efficiency and conversion rates.

Collaboration & Reporting

• Partner with Operations and other Team Leaders to share best practices and ensure alignment with company goals.
• Escalate operational risks and improvement opportunities to senior management.
• Maintain detailed weekly reports via Monday.com and ensure transparent communication with stakeholders.

Qualifications & Requirements

• Experience: At least 2–3 years in a similar role, with 1–2 years in outbound sales.
• Proven track record in sales coaching and/or sales training.
• Strong leadership, communication, and motivational skills.
• Excellent phone etiquette and interpersonal skills.
• Ability to analyze data and translate insights into action plans.
• Creative thinker with the ability to adapt quickly to change.
• Proficient in Microsoft Office; experience with CRM systems, sales tracking tools, and platforms like Monday.com or Zingtree is a plus.
• Experience working with American culture/demographics is preferred