[Remote] Director of Sales And Business Development

Note: The job is a remote job and is open to candidates in USA. Buckled In is hiring a Director of Sales and Business Development to grow revenue in alternative student transportation. The role focuses on acquiring school district and agency customers, expanding existing partnerships, and managing territory strategy.

Responsibilities

• Identify and penetrate new accounts and markets: School districts, charter networks, social services agencies, and education providers across your territory
• Navigate complex procurement: Master the RFP process, build consensus among multiple stakeholders (transportation directors, special ed coordinators, social services personnel, finance, operation, superintendents)
• Build pipeline: You'll own everything from prospecting to close. We are looking for people have pipeline development experience, including lead generation, working existing leads and moving customers through the sales funnel. We provide marketing support, but this is a true hunter role
• Close meaningful deals: Average contract value $250K-$1M+ annually with multi-year terms
• Become the trusted advisor: Your existing customers will look to you to solve new challenges and expand service offerings
• Identify growth opportunities: Analyze route data, service metrics, and customer feedback to uncover expansion potential
• Drive retention and upsell: Protect your book of business while systematically growing revenue per customer by 15-30% annually
• Leverage cross-functional teams: Partner with operations to ensure flawless service delivery that creates expansion opportunities
• Own your numbers: Develop and execute quarterly territory plans with clear revenue targets and monthly activity metrics
• Be data-driven: Use CRM analytics to prioritize accounts, forecast accurately, and optimize your time
• Represent the brand: Attend industry conferences, speak on panels, and position Buckled In as the thought leader in alternative student transportation

Skills

• Industry Experience: Education and Student Transportation Required
• 5-10+ years in B2B sales with proven new business development and account growth success
• 5-10 + years of B2B sales success  with documented evidence of exceeding quota in both new business development and account management
• Complex sale expertise:  You've navigated long sales cycles (3-9 months), multiple stakeholders, procurement processes, and contract negotiations
• Proven prospecting ability:  Track record of self-generating pipeline through cold outreach, networking, and creative business development
• Account growth DNA:  You don't just maintain relationships—you systematically expand them through consultative selling and value creation
• Presentation excellence:  You can command a room or a Zoom, tell compelling stories, and articulate complex value propositions simply
• Data-driven approach:  Comfortable with CRM systems (HubSpot preferred), Excel-based analysis, and using metrics to drive your process
• Education sector experience:  Previous sales into school districts, education agencies, or government entities
• Transportation or logistics background:  Understanding of fleet operations, routing, compliance, or related industries
• Hunter mentality with farmer patience:  Aggressive prospecting balanced with relationship nurturing
• Mission alignment:  Genuinely motivated by making a difference for vulnerable student populations
• Entrepreneurial mindset:  You think like a business owner, not just a salesperson
• Resilient and resourceful:  Government sales cycles can be long and unpredictable—you stay focused and creative
• Self-directed:  Thrives working remotely with minimal supervision; takes initiative without direction
• Must be based in US
• Bachelor's degree in business, sales, or related field (or equivalent experience)
• Proficient in MS Office (Excel, PowerPoint, Word), Google Suite, AI platforms and CRM systems
• Valid driver's license  and proof of auto insurance required
• Public sector procurement:  Experience navigating RFPs, government contracts, and public bidding processes
• Social impact sales:  Track record selling mission-driven services where relationship and trust matter as much as price

Benefits

• Uncapped, accelerating commission on all new and expansion revenue above quota
• Medical and vision insurance
• Minimum 120 hours PTO + 13 paid holidays
• 401(k) plan
• $250 annual home office stipend
• All territory travel expenses covered
• Flexibility: Structure your day around customer needs
• Remote work with frequent territory travel, up to 40% during key sales windows (overnight travel)
• Marketing materials, case studies, RFP response templates, and demo access
• Highly engaged service delivery team
• Access to route performance, customer satisfaction scores, and financial metrics
• Weekly 1:1s with sales leadership
• Industry conference attendance, sales training, and skill development budget
• Leadership opportunities: Grow into Senior Sales roles and build teams to support growth
• Strategic influence: Help shape our market expansion and service offerings
• Inclusive culture: Values-driven, caring environment where you're respected

Company Overview