Enterprise Business Development Representative (US Remote)

Jackrabbit Technologies • Huntersville, NC

3d • Remote

About The Position

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.

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.

Requirements

• 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

Nice To Haves

• 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
• 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

Responsibilities

• 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
• 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
• 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
• 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
• 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
• 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.

Benefits

• We work remotely. We always have - we always will!
• Medical, Dental, Vision, Flexible Spending, HSA and Dependent Care Accounts.
• 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.
• 401(k) with a generous company match, access to financial planning.
• Paid Time Off, Paid Parental, Paid Caregiver and Sabbatical leaves.
• Annual allowance for professional development.
• Paid Time to volunteer in your community.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 101-250 employees