Sales Development Representative - 1099

Gilder Search Group; Northern (KY); Hybrid; USD 23,000 - 32,000; Full time

Job summary

Gilder Search Group is seeking a self-driven 1099 IT Sales Representative to prospect and close consultative technology solutions for SMBs. This outside sales role emphasizes commission and independence, requiring you to manage your own schedule and pipeline.

You will sell services like managed IT, cybersecurity, cloud, and telecom, build relationships, and drive revenue through new business and upsell opportunities. Remote position with flexible hours and potential for growth.

Qualifications

• 2+ years of B2B sales experience in IT services, MSPs, or tech solutions.
• Proven ability to prospect and close new business.
• Experience selling to small and midsize businesses.
• Familiarity with CRM systems and sales pipeline management.
• Strong communication, presentation, and relationship-building skills.
• Self-motivated, organized, and goal-oriented.

Responsibilities

• Prospect and develop new business via cold calls, networking, referrals, email outreach, and local activity.
• Sell IT services (MSP, cybersecurity, cloud, backup) to SMBs.
• Conduct discovery calls to identify needs and propose solutions.
• Assist with technical demos and tailor IT solutions.
• Maintain client relationships with regular communication and account management.
• Identify upsell opportunities and expand service portfolio.
• Build and maintain a sales pipeline using CRM with consistent follow-up.
• Prepare proposals, quotes, and presentations with internal staff.
• Meet or exceed monthly and quarterly sales goals.
• Represent the company professionally in client interactions.
• Maintain records of prospecting activities and closed business.

Skills

Prospecting

Closing

CRM proficiency

Communication

Relationship-building

Self-motivation

Organization

Tools

CRM systems

Job description

We are seeking a self-driven 1099 IT Sales Representative to prospect and close consultative tech solutions (Managed Services, Cybersecurity, Telecom) for SMBs. This commission-focused role offers high earning potential, flexibility, and growth for a proven hunter with a track record in B2B technology sales. We are looking for a candidate who is an experienced outside sales professional, thriving on prospecting, relationship building, and closing consultative technology solutions for small and midsize businesses.

This is an independent contractor role, so the person must be comfortable managing their own schedule, pipeline, and sales activity.

• Location: Remote
• Compensation: $20 per hour
• Commission Structure: Commission paid on new business closed and/or collected revenue
• Contractor responsible for their own taxes, insurance, and business expenses unless otherwise agreed in writing.

Key Responsibilities

• Prospect and develop new business opportunities through cold calling, networking, referrals, email outreach, and local market activity.
• Sell IT services such as managed IT, help desk support, cybersecurity, cloud solutions, backup and disaster recovery, and related offerings.
• Conduct discovery calls to identify client needs and recommend appropriate solutions.
• Assisting with technical demos and designing tailored IT solutions.
• Maintaining ongoing relationships with clients, including regular communication, account management, and identification of additional business opportunities to ensure client retention and satisfaction.
• Identifying upsell opportunities and expanding the service portfolio.
• Build and maintain a sales pipeline using CRM tools and consistent follow-up.
• Prepare proposals, quotes, and presentations in coordination with internal technical staff as needed.
• Meet or exceed monthly and quarterly sales goals.
• Represent the company professionally in all client interactions.
• Maintain accurate records of prospecting activity, sales opportunities, and closed business.

Requirements

• 2+ years of B2B sales experience in IT services, managed services, telecom, software, or technology solutions.
• Proven ability to prospect and close new business.
• Experience selling to small and midsize businesses.
• Familiarity with CRM systems and sales pipeline management.
• Strong communication, presentation, and relationship-building skills.
• Self-motivated, organized, and goal-oriented.

Preferred Attributes

• Background selling managed service provider (MSP) solutions.
• Experience with cybersecurity, cloud, VOIP, copier/office technology, or adjacent business technology markets.
• Existing local business network in the target markets.
• Ability to sell consultatively rather than transactionally.

Performance Expectations

• Weekly prospecting activity targets.
• Monthly appointments set and sales closed.
• Consistent follow-up and client relationship management.