IT Sales Careers in Naples & Southwest Florida

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Sales Development Representative / Business Development Representative

NerdSquad | South Florida | Work From Home / Local

NerdSquad is looking for an ambitious, entrepreneurial sales professional who wants more than just another SDR or BDR job. This is an opportunity for someone who wants to get in early, make an impact, help shape how we sell, and grow along with the company.

The Opportunity

Initially, your job will be simple: create conversations with businesses that could benefit from NerdSquad. You'll prospect, identify opportunities, build relationships, qualify potential customers, and work directly with company leadership to turn those opportunities into new business. But we're not looking for someone who wants to remain an SDR forever — as NerdSquad grows, we want this person to take increasing ownership of the sales process, help refine our sales playbook, participate in hiring future salespeople, and ultimately move into a Sales Manager / sales leadership role. For the right person, there's also an equity opportunity as the company continues to grow.

What You'll Do

• Prospect and develop new B2B opportunities throughout South Florida
• Identify and reach decision makers through phone, email, LinkedIn, networking, referrals, and creative outbound strategies
• Qualify prospective customers and schedule meaningful sales meetings
• Build and maintain a healthy sales pipeline
• Follow up consistently with prospects and nurture longer-term opportunities
• Learn NerdSquad's managed IT, cybersecurity, cloud, communications, and AI offerings
• Work directly with leadership on messaging, targeting, campaigns, and sales strategy
• Assist in creating relevant content for our website and socials
• Maintain accurate activity, pipeline, and opportunity information in our CRM
• Attend local networking, business, and community events when appropriate
• Help improve our sales processes as we learn what works
• Over time, take increasing ownership of sales strategy, process, hiring, coaching, and team performance

Who We're Looking For

We care more about ability, drive, judgment, and personality than checking every box on a résumé. You may be a great fit if you:

• Have experience in SDR, BDR, business development, account management, or B2B sales
• Are comfortable picking up the phone and starting conversations
• Can communicate naturally with business owners and executives
• Are persistent without being annoying
• Are organized and disciplined enough to work independently
• Understand that good sales is about discovering problems and creating value, not reading a script
• Are comfortable learning technology and explaining it in plain English
• Want responsibility and career growth rather than simply hitting an activity quota
• Enjoy working in a smaller entrepreneurial company where your ideas can actually change how things are done
• Would eventually like to build and lead a sales team

Experience selling managed IT services, cybersecurity, SaaS, telecommunications, professional services, or other B2B technology solutions is a plus, but it is not required.

Location & Work Environment

NerdSquad currently operates with a distributed workforce, so this position can primarily be performed from home. However, this is not a location-independent remote position — we want this person located in South Florida, with opportunities to meet prospects and customers in person, attend networking events, collaborate with leadership, and become part of the local business community. We believe the combination of work-from-home flexibility and a strong local presence gives us the best of both worlds.