Director of Sales And Business Development

Location: Remote -must be based in US – Opportunities open across the US

Industry Experience:Education and StudentTransportation Required

Experience Level: 5-10+ years in B2B sales with proven new business development and account growth success

Compensation: Commensurate with experience (base + uncapped commissions)

WHY THIS ROLE MATTERS
Every day, you'll help ensure that vulnerable students—those experiencing homelessness, in foster care, or with special needs—get to school safely and consistently. Your sales success directly translates to more children accessing the education they deserve.

This ismorethan mission-driven work—it’shigh-growth B2B sales in an underserved marketworth over $30 billion,withsubstantial room to expand.

THE OPPORTUNITY
We're looking for a hunter: someone who gets energized by opening doors with new school districts while simultaneously growing revenue from existing partnerships. You'll own your territory like an entrepreneur, with the backing of 29+ years of operational excellence and best-in-class technology.

This role is perfect for you if:

You've proven you can prospect, close complex deals, and expand existing accounts

You're tired of selling commoditized products and want to represent something that truly matters

You want senior-level ownership of your territory without the startup risk

You thrive with autonomy and are comfortable managing remote sales activity

WHAT YOU'LL DO
Drive New Revenue (70% of your time)

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

Expand Existing Partnerships (20% of your time)

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

Strategic Territory Management (10% of your time)

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

SUCCESS METRICS (First 12 Months)

Quota attainment: 100%+ of annual revenue target ($2M-$3M in new + expansion revenue)

Pipeline development: 3-4x pipeline coverage consistently maintained

Account penetration: Expand revenue by 20 to 30%+ across existing customer base

Customer retention: Maintain 95%+ renewal rate in your territory

WHAT MAKES YOU THE IDEAL CANDIDATE
Required Experience & Skills

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

Additional Preferred Experience

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

Personal Attributes

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

WHY BUCKLED IN?
The Market Opportunity

Underserved and growing: Alternative student transportation represents billions in addressable market with limited specialized competition

Legislative tailwinds: McKinney-Vento Act and foster care education requirements create consistent, federally mandated demand

Sticky revenue: Multi-year contracts with high retention rates and strong expansion potential

Our Competitive Advantages

Technology leadership: Proprietary routing and family communication platforms

29 years of operational excellence: We deliver on our promises, which makes your sales job easier

People-first culture: Unlike typical fleet operators, we prioritize driver consistency and family relationships

Mission-driven organization: Privately held and focused on impact, not quarterly earnings

This isn't a dead-end sales job. High performers can expect:

Leadership opportunities: Grow into Senior Sales roles and build teams to support growth

Strategic influence: Help shape our market expansion and service offerings

What We Provide

Operations partnership: Highly engaged service delivery team that makes renewals and expansion easier

Real-time data: Access to route performance, customer satisfaction scores, and financial metrics

Autonomy with support: Weekly 1:1s with sales leadership, but you control your day-to-day

Professional development: Industry conference attendance, sales training, and skill development budget

COMPENSATION & BENEFITS

Earnings Potential

Base Salary: Commensurate with experience

Commission Structure: Uncapped, accelerating commission on all new and expansion revenue above quota

Health Insurance: Medical, vision

Generous Time Off: Minimum 120 hours PTO + 13 paid holidays

Retirement: 401(k) plan

Home Office Support: $250 annual stipend

Travel Reimbursement: All territory travel expenses covered

Intangibles

Flexibility: Structure your day around customer needs

Mission impact: Go to bed knowing you helped kids get to school

Inclusive culture: Values-driven, caring environment where you're respected

Stability: Established company with 29-year track record, not a startup gamble

LOGISTICS & REQUIREMENTS

Location: Must be based in US (specific territory to be finalized based on candidate location)

Work Model: Remote with frequent territory travel, up to 40% during key sales windows (overnight travel)

Education: Bachelor's degree in business, sales, or related field (or equivalent experience)

Technology: Proficient in MS Office (Excel, PowerPoint, Word), Google Suite, AI platforms and CRM systems

Valid driver's license and proof of auto insurance required

ABOUT BUCKLED IN
For over 29 years, Buckled In has been ensuring that life's challenges don't prevent students from accessing quality education. We specialize in transportation for students experiencing homelessness (McKinney‑Vento Act), those in foster care, and children with special needs and IEPs.

Consistency: Same driver, same experience, every day

Reliability: Industry‑leading on‑time performance and service quality

Transparency: Real‑time tracking and communication for families and schools

Compliance and Safety: Deep expertise in federal, state, and local transportation regulations

We're a privately‑held company, which means we make decisions based on impact to students and families—not shareholder pressure. We move fast, innovate constantly, and truly live our values.

Buckled In is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

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