Director, Inside Sales

Summary

Join Human Interest as the Director of Inside Sales Representatives and lead a high-performing team of sales professionals across three distinct functions: Inside Sales Representatives (ISR), Small Market AEs, and Sales Development Representatives (SDR). You will coach, mentor, and develop sales leaders, ensuring best practices and driving continuous improvement. This role requires strong leadership, data analysis, and communication skills to manage team performance, provide strategic guidance, and achieve sales targets. Human Interest offers a competitive salary and benefits package, including a robust 401(k) plan, comprehensive health insurance, generous PTO, and various wellness programs. The company fosters a collaborative and supportive culture focused on employee growth and achieving its mission of expanding access to retirement benefits.

Requirements

• Proven experience in a Sales Development Leader role or a similar Leader position
• Minimum of 8+ years of Sales team management experience
• Strong understanding of sales processes, lead generation, sales engagement tools (Outreach and Gong) and CRM tools (Salesforce)
• Technologically savvy; able to pick up new systems and technologies quickly
• Excellent communication, coaching, and interpersonal skills
• A curious mindset and ability to dig into data and understand the reasons behind performance changes
• Ability to analyze data, draw insights, and make strategic data-driven decisions
• Self-motivated and able to work in a fast-paced, dynamic environment
• Proven expertise in coaching and developing team members, providing constructive and actionable feedback to drive consistent performance and growth; and fostering a culture of continuous improvement and development across the team
• Exceptional record of leading high-performing managers who consistently drive month-over-month success, achieving and exceeding sales quotas and targets at scale
• Demonstrated ability to strategically guide and support leaders through shifting priorities, adapting to new strategies as needed to outpace organizational goals and enhance team-wide transparency and performance
• Strong interpersonal, organizational, and stakeholder management skills able to present to leadership on results of sales performance; translating team performance into easy-to-understand goals, metrics, and benchmarks, aligning on overall sales leadership vision
• Proven experience in presenting performance insights and aligning team goals with overarching sales leadership objectives

Responsibilities

• Manage our ISR, SDR, and Small Market team Leaders to establish and meet or exceed key performance metrics and conversion benchmarks
• Maintain a comprehensive view of the team’s performance, identifying trends, and taking strategic actions to drive continuous improvement
• Coach, mentor, and develop sales Leaders in areas of process improvement, productivity, and inside sales best practices
• Facilitate Leader training on employee development, guiding career growth, onboarding, and performance feedback
• Align with Partnerships and Business Leads to ensure optimal lead flow and quality, setting targeted outreach strategies with Team Leaders
• Maintain open communication with the VP of Sales, regularly sharing team updates, performance insights, and areas for process improvement
• Conduct weekly 1:1s with Leaders, focusing on personal coaching, quota achievement, and strategic improvement areas
• Proactively identify and address missed opportunities, ensuring lead quality, follow-up, and customer engagement
• Provide accurate weekly forecasts to the VP of Sales and monitor team performance against goals
• Share actionable weekly insights with the VP of Sales on performance concerns, successes, and strategic process improvements
• Oversee and refine performance metrics, ensuring alignment with organizational goals and sales benchmarks

Preferred Qualifications

Bachelor's degree in Business, Marketing, or a related field

Benefits

• A great 401(k) plan: Our own! Our 401(k) includes a dollar-for-dollar employer match up to 4% of compensation (immediately vested) and $0 plan fees
• Top-of-the-line health plans, as well as dental and vision insurance
• Generous PTO and parental leave policies
• Addition Wealth - Unlimited access to digital tools, financial professionals, and a knowledge center to help you understand your equity and support your financial wellness
• Lyra - Enhanced Mental Health Support for Employees and dependents
• Carrot - Fertility healthcare and family forming benefits
• Candidly - Student loan resource to help you and your family plan, borrow, and repay student debt
• Monthly work-from-home stipend; quarterly lifestyle stipend
• Employee Resource Groups including Veterans, Lift Ev’ry Voice, Pride, LatinX, Families, and Women in Tech
• Fun online and regional events and celebrations and department and company offsites
• The vast majority of our positions can be 100% remote
• Base salary for this position spans $105,000 - $110,000
• Variable target of $110,000