Sales Development Representative
Fully Remote Remote Worker - N/A
Description

Your Strengths

  • You are energized by connecting with people and starting conversations. You enjoy uncovering challenges, building relationships, and helping others discover solutions that genuinely make their work easier.
  • You are proactive and resilient. You’re comfortable reaching out, hearing “not right now,” and continuing forward with positivity and persistence.
  • You communicate clearly and confidently. Whether through email, phone, or LinkedIn, you know how to engage people in a professional and authentic way.
  • You are naturally curious. You ask thoughtful questions to understand a prospect’s goals, challenges, and operational realities.
  • You are goal-oriented and self-driven. You enjoy working toward measurable targets and continuously improving your approach.
  • You thrive in collaboration. You work closely with Account Executives and the broader Sales team because you understand that strong pipeline generation is a team effort.

What You’ll Do

Prospecting & Lead Generation

  • Identify and engage prospective school district leaders through outbound calls, emails, social outreach, and other strategic prospecting efforts.
  • Build pipeline by generating new opportunities for the sales team across assigned territories and campaigns.
  • Research school districts, staffing trends, and organizational needs to personalize outreach and improve engagement.
  • Maintain a consistent cadence of outreach activities while balancing quality and efficiency.

Lead Qualification & Discovery

  • Conduct discovery conversations to understand prospect needs, challenges, and fit for Red Rover’s solutions.
  • Ask thoughtful questions that uncover operational pain points and opportunities for improvement.
  • Qualify inbound and outbound leads based on established criteria and sales priorities.
  • Effectively communicate Red Rover’s value proposition in a way that resonates with K–12 education professionals.

Sales Team Collaboration

  • Partner closely with Account Executives and sales leadership to align prospecting efforts with territory goals and pipeline strategy.
  • Coordinate smooth handoffs of qualified opportunities to the sales team.
  • Share prospect insights, market feedback, and common objections to help improve messaging and outreach strategies.
  • Participate in team meetings, coaching sessions, and collaborative sales initiatives.

CRM & Pipeline Management

  • Maintain accurate and organized records of prospect activity, conversations, and follow-up tasks within HubSpot.
  • Track outreach effectiveness and contribute to improving prospecting workflows and processes. 
  • Help ensure pipeline visibility and forecasting accuracy through disciplined CRM management.

Continuous Learning & Market Awareness

  • Stay informed on K–12 education trends, staffing challenges, and the competitive landscape.
  • Continuously develop product knowledge and understanding of school district operational needs.
  • Refine outreach messaging and communication approaches through coaching, feedback, and ongoing learning
Requirements
  • Strong communication and interpersonal skills with the ability to build rapport quickly.
  • A proactive, goal-oriented mindset with strong follow-through and persistence.
  • Strong problem-solving and critical-thinking abilities.
  • Comfort initiating conversations and engaging prospective customers.
  • Ability to work independently in a remote environment while collaborating effectively with a team.
  • Highly organized with strong attention to detail.
  • Experience with CRM systems such as HubSpot is a plus.
  • Experience in sales, customer service, recruiting, or other relationship-focused roles is helpful but not required
  • Interest in education, technology, or helping education solve operational challenges is a plus