Note: The job is a remote job and is open to candidates in USA. Red Rover is seeking an Account Executive to drive complex B2B sales opportunities within an assigned region. The role focuses on consultative selling to school districts, strategic account development, revenue and pipeline ownership, cross-functional deal execution, forecasting, and building trusted customer relationships.
Responsibilities
- Own the sales cycle for new business opportunities within an assigned region, with particular 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
- 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
- Willingness to travel for strategic customer meetings, conferences, regional events, and company gatherings
- Experience selling to K–12 school districts or other public-sector/institutional organizations is strongly preferred
- Experience selling HCM, HR, payroll, ERP, or workforce technology is a plus
Company Overview