Strategic EdTech Account Executive: Complex Sales & Growth

Red Rover; United States; On-site; USD 120,000 - 180,000; Full time

Job summary

Red Rover is seeking a results-driven senior sales professional in the United States to own complex, multi-stakeholder deals within K-12 districts. You will lead discovery, develop account strategies, and guide opportunities from initial contact to closing.

This role emphasizes consultative selling, cross-functional collaboration, accurate forecasting, and CRM discipline, with travel for strategic meetings.

Qualifications

• 4–7+ years of successful B2B sales experience, ideally within SaaS, enterprise technology, EdTech, HCM, ERP, or another complex solution environment.
• Demonstrated success owning and closing complex, multi-stakeholder sales opportunities.
• Proven track record of meeting or exceeding revenue targets.
• Strong consultative discovery, presentation, negotiation, and closing skills.
• Experience navigating longer sales cycles, formal procurement processes, and sophisticated buying committees.
• Strong business judgment and ability to develop strategic approaches to accounts and opportunities.
• Excellent written and verbal communication skills with executive-level presence.
• Strong forecasting, pipeline management, and CRM discipline.
• Ability to operate independently while collaborating effectively with regional leadership and cross-functional partners.

Responsibilities

• Own the sales cycle for new business opportunities within an assigned region, with responsibility for larger, more strategic, or complex opportunities.
• Lead consultative discovery with district stakeholders to understand business challenges, operational workflows, strategic priorities, decision criteria, and desired outcomes.
• Develop account and deal strategies that account for multiple stakeholders, competitive dynamics, procurement requirements, budgets, and complex buying processes.
• Guide opportunities from initial discovery through evaluation, proposal, negotiation, contracting, and close.
• Develop relationships with key decision-makers and influencers across school districts, including HR, Finance, Payroll, Technology, and executive leadership.
• Serve as a trusted advisor who can connect district challenges with Red Rover's growing portfolio of solutions.
• Navigate complex buying committees and build consensus among stakeholders with different priorities.
• Maintain credibility throughout the sales process by setting thoughtful, realistic expectations about Red Rover's capabilities and customer experience.
• Own individual revenue targets and consistently work toward meeting or exceeding established goals.
• Build and maintain sufficient pipeline through a combination of self-generated opportunities and partnership with SDRs, Marketing, and regional sales leadership.
• Develop strategic approaches to priority accounts and high-value opportunities within the region.
• Partner with the Regional Sales Manager to identify market opportunities, regional trends, and accounts requiring coordinated sales strategies.
• Develop and execute thoughtful strategies for complex and competitive opportunities.
• Coordinate Solutions Consultants, Product experts, Integrations, Finance, Leadership, and other internal partners when their expertise is needed during the sales process.
• Partner with Marketing and Product Marketing to leverage relevant messaging, competitive intelligence, customer stories, and market insights.
• Navigate pricing, proposals, procurement, and contract negotiations while balancing customer needs with Red Rover's business objectives.
• Maintain a highly accurate and current pipeline within HubSpot.
• Provide thoughtful forecasts based on customer behavior, deal progression, and clearly defined next steps—not optimism alone.
• Identify deal risks early and proactively develop strategies to address them.
• Use sales performance data, win/loss insights, and coaching to continually improve effectiveness.
• Bring insights from customers and the market back to Sales leadership, Product, Marketing, and other teams.
• Share best practices and lessons learned with other members of the Sales organization.
• Serve as a resource and informal mentor to developing sellers when appropriate.
• Stay deeply informed about Red Rover's products, competitive landscape, K–12 market, and evolving district needs.
• Represent Red Rover at conferences, customer meetings, presentations, and industry events as needed

Skills

Consultative selling

Stakeholder management

Forecasting

CRM discipline

Cross-functional selling

Negotiation

Strategic account management

Tools

HubSpot

Salesforce

Job description

Red Rover is seeking a results-driven senior sales professional in the United States to own complex, multi-stakeholder deals within K-12 districts. You will lead discovery, develop account strategies, and guide opportunities from initial contact to closing.

This role emphasizes consultative selling, cross-functional collaboration, accurate forecasting, and CRM discipline, with travel for strategic meetings.