Enterprise Business Development Representative (US Remote)

Welcome to Jackrabbit Technologies.

Jackrabbit Technologies is the leading provider of software and services that help youth activity centers -- gymnastics, dance, cheer, swim, music, childcare, and others -- grow and operate efficiently. We are an entrepreneurial-minded, rapidly growing SaaS company that has been recognized as one of the Best Places to Work in North Carolina and one of North Carolina’s Top Industry-Driven Technology Companies. Jackrabbit Technologies’ SaaS solution powers over 7000 clients in 35 countries around the world.

Our culture empowers YOU.

We hire people passionate about what they do, provide them with the tools to succeed, and then get out of their way! Living our vision, mission, and values, our people are what make Jackrabbit Technologies an awesome place to work. And that “awesome place” is virtual--all of our employees enjoy the privilege of working remotely. We always have and always will. We are interested in speaking to qualified candidates who are US Citizens or Green Card holders with no special circumstances living in the US. We are not able to sponsor visas.

What you'll do.

As an Enterprise Business Development Representative, you will serve as a flexible sales resource responsible for driving new customer acquisition across both Enterprise and SMB segments based on business priorities. You will manage the complete sales cycle from initial prospect engagement through contract closure, with a primary focus on complex Enterprise opportunities while also supporting high-velocity SMB sales when needed. This role requires the versatility to navigate consultative, multi-stakeholder Enterprise sales processes as well as efficient SMB conversion strategies.

Enterprise Lead Generation & Prospecting

• Conduct strategic outbound prospecting for Enterprise accounts through targeted calls, emails, LinkedIn, and other professional channels
• Research and identify high-value Enterprise prospects including multi-location operations, regional chains, and large independent facilities
• Develop account-based prospecting strategies for target Enterprise organizations
• Build relationships with decision-makers at the C-suite and senior leadership levels
• Execute sophisticated prospecting campaigns designed to engage complex buying committees
• Manage inbound Enterprise leads with timely, professional follow-up that reflects the consultative nature of Enterprise sales
• Track all Enterprise prospecting activities in HubSpot with detailed notes on stakeholder mapping and organizational dynamics
  
  

SMB Lead Generation & Prospecting

• Support SMB pipeline development during high-volume periods or as business needs dictate
• Manage inbound SMB leads with rapid response and efficient qualification
• Conduct high-velocity outbound prospecting for SMB accounts when assigned
• Execute on established SMB prospecting cadences and playbooks
• Adapt communication style for SMB decision-makers who often require faster, more transactional sales approaches
• Maintain SMB pipeline in HubSpot with accurate tracking and forecasting
  
  

Qualification & Discovery

• Conduct comprehensive discovery calls to understand prospect needs across both Enterprise and SMB segments
• Qualify prospects based on segment-specific criteria including organizational complexity, budget authority, implementation readiness, and decision-making processes
• Identify and map key stakeholders in Enterprise accounts, understanding roles, influences, and buying dynamics
• Uncover pain points, business requirements, and strategic objectives that Jackrabbit's solution addresses
• Assess prospect fit and readiness to prioritize opportunities effectively
• Document detailed qualification information in HubSpot to support sales forecasting and pipeline management
  
  

Product Demonstration & Presentation

• Deliver tailored Enterprise demonstrations that address complex, multi-stakeholder needs and organizational requirements
• Conduct efficient SMB demonstrations that focus on key value drivers and rapid decision-making
• Customize presentations to highlight features, integrations, and capabilities most relevant to each prospect's segment and use case
• Handle sophisticated objections in Enterprise deals involving procurement, IT security, data privacy, and implementation complexity
• Articulate ROI and business value in terms that resonate with different organizational levels and business segments
• Coordinate demonstration support from technical resources or management when needed for complex Enterprise opportunities
  
  

Sales Process & Deal Management

• Manage full sales cycles for both Enterprise and SMB opportunities from initial contact through contract closure
• Navigate complex Enterprise buying processes with multiple stakeholders, longer timelines, and formal procurement requirements
• Execute efficient SMB sales cycles focused on speed-to-close and streamlined decision-making
• Maintain accurate pipeline forecasting across both segments in HubSpot
• Meet or exceed sales quotas with appropriate mix of Enterprise and SMB revenue
• Coordinate smooth handoffs to Client Success teams for implementation and onboarding
  
  

Adaptability & Market Intelligence

• Drives Results - Consistently achieving sales results, even under tough circumstances
• Customer Focus - Building strong customer relationships and delivering customer-centric solutions
• Communicates Effectively - Developing and delivering multi-mode communications that convey clear understanding of the unique needs of different audiences
• Persuades - Using compelling arguments to gain the support and commitment of others
• Action Oriented - Taking on new opportunities and tough challenges with a sense of urgency, high energy and enthusiasm
• Builds Networks - Effectively building formal and informal relationship networks inside and outside the organization
• Nimble Learning - Actively learning through experimentation when tackling new problems, using both successes and failures as learning fodder
• Demonstrates Self-Awareness - Using a combination of feedback and reflection to gain productive insight into personal strengths and weaknesses.
  
  

What You're About.

You are a versatile, ambitious sales professional who thrives in dynamic environments and enjoys the challenge of working across different sales motions. You're equally comfortable building complex, consultative relationships with Enterprise executives and executing efficient, high-velocity sales with SMB decision-makers. You're organized, resilient, and motivated by achieving results in diverse selling scenarios. You have strong communication skills, business acumen, and the adaptability to shift gears based on organizational priorities. You're eager to learn, coachable, and excited about developing expertise across the full spectrum of B2B SaaS sales.

Experience And Qualifications

Required Experience

• 2-4 years of B2B sales experience, preferably in SaaS or technology with exposure to different market segments
• Demonstrated success in meeting or exceeding sales quotas across diverse opportunity types
• Experience with consultative, multi-stakeholder sales processes or strong desire to develop Enterprise sales skills
• Proven ability to conduct professional product demonstrations and presentations
• Strong communication skills across phone, email, video, and social channels
• CRM experience (HubSpot preferred) with disciplined pipeline management and forecasting
• Adaptability and flexibility to shift focus between different sales motions and priorities
• Self-motivated and goal-oriented with ability to work independently in a remote environment
  
  

Preferred Qualifications

• Bachelor's degree in Business, Marketing, Communications, or related field
• Experience selling to both Enterprise and SMB segments in previous roles
• Familiarity with account-based selling strategies for Enterprise opportunities
• Experience in the youth activity/education industry (gymnastics, dance, swim, childcare)
• Knowledge of SaaS sales methodologies (MEDDIC, Challenger, Sandler, etc.)
• Experience with sales engagement platforms (Outreach, SalesLoft, LinkedIn Sales Navigator)
• Understanding of complex B2B buying processes including procurement and vendor evaluation
  
  

Skills & Abilities

• Excellent verbal and written communication with ability to adjust tone and style for different audiences
• Strong presentation skills for both intimate SMB demos and formal Enterprise presentations
• Active listening and discovery capabilities to uncover needs across organizational types
• Time management and organizational skills to balance competing priorities and pipeline segments
• Objection handling and negotiation abilities for both simple and complex sales scenarios
• Business acumen to understand different operational models and decision-making processes
• Coachability and growth mindset with desire to develop Enterprise sales expertise
• Comfort with technology and ability to quickly learn new tools and platforms
• Positive attitude and competitive drive with resilience through diverse sales challenges
  
  

Core Competencies

• Drives Results - Consistently achieving sales targets across both Enterprise and SMB segments through focused effort and adaptability
• Customer Focus - Understanding diverse customer needs and positioning solutions that deliver value regardless of organization size
• Communicates Effectively - Tailoring communication style and content for C-suite executives, operations managers, and small business owners
• Persuades - Using appropriate influence techniques for consultative Enterprise deals and efficient SMB conversions
• Action Oriented - Taking initiative to generate opportunities and move deals forward with appropriate urgency for each segment
• Resilience - Persisting through rejection, long Enterprise sales cycles, and high-volume SMB prospecting while maintaining energy
• Nimble Learning - Quickly absorbing different sales methodologies, product positioning, and buyer dynamics across segments
• Business Insight - Understanding diverse business models from small independents to multi-location enterprises
• Manages Ambiguity - Thriving in a flexible role that requires shifting priorities and approaches based on business needs
  
  

What You Will Love About Us.

• Our Culture!
• We work remotely. We always have - we always will!
• Our Health and Wellness Benefits. Medical, Dental, Vision, Flexible Spending, HSA and Dependent Care Accounts.
• We help you with the unexpected. Company-Paid Disability and Life Insurance. Opportunity to elect Critical Illness and Accident Insurance. Plus confidential access to legal and life counseling and mental health support available 24/7.
• Your future looks bright at Jackrabbit. 401(k) with a generous company match, access to financial planning.
• We pay you to play, rest, recharge and balance your life. Paid Time Off, Paid Parental, Paid Caregiver and Sabbatical leaves.
• You will grow your skills with us. Annual allowance for professional development.
• We give back. Paid Time to volunteer in your community.
  
  

Jackrabbit is committed to providing a workplace free from discrimination or harassment. We expect every member of the Jackrabbit team to do their part to cultivate and maintain an environment where everyone has the opportunity to feel included and is afforded the respect and dignity they deserve.

Decisions related to hiring, compensating, training, evaluating performance, or terminating are made fairly, and we provide equal employment opportunities to all qualified candidates and employees. We examine our unconscious biases and take responsibility for always striving to create an inclusive environment that makes every employee and candidate feel welcome.