B2B Lead Generation Specialist | LinkedIn & Upwork | Remote

Location: Remote, Eastern Europe

Compensation: Hourly pay + bonus per qualified call

About Us

Out of the Box Systems is a technology company providing custom software development and engineering services to international clients.

Our Lead Generation Strategist is developing the outreach strategy and playbook. We are looking for a proactive, organized Lead Generation Specialist to put this strategy into practice through prospect research, personalized outreach, and consistent follow-up.

The Role

We provide the target audience, messaging frameworks, and guidance. You research relevant prospects, adapt messages to their needs, manage outreach on LinkedIn and Upwork, and turn interested replies into qualified meetings.

This role requires independent judgment, clear written communication, and attention to detail.

Your Responsibilities

• Prospect research: Identify decision-makers, including CEOs, CTOs, and founders, whose companies match our Ideal Customer Profile.
• Personalized outreach: Write relevant opening messages based on a prospect’s role, company, projects, or business needs.
• LinkedIn outreach: Initiate conversations, follow up consistently, and manage ongoing communication.
• Upwork proposals: Identify suitable opportunities and prepare tailored proposals that address the client’s specific requirements.
• Inbox management: Respond promptly, clarify potential needs, and coordinate discovery calls with our team.
• Tracking: Maintain accurate records of outreach activity, replies, follow-ups, and booked meetings.
• Feedback: Share recurring objections and useful insights with the strategist to help improve the playbook.

What We Are Looking For

• Strong written English, approximately B2+/C1, with the ability to write clear, natural, professional messages.
• Practical experience with LinkedIn outreach and Upwork proposals.
• Familiarity with LinkedIn Sales Navigator.
• The ability to research companies and distinguish relevant opportunities from poor matches.
• Consistent follow-through, accurate recordkeeping, and the ability to work independently.
• Willingness to follow an established process, accept feedback, and suggest improvements.

Experience generating leads for software development, IT outsourcing, or engineering services is an advantage.

What We Offer

• Remote collaboration.
• An outreach strategy, defined target audience, and messaging frameworks.
• Support from our strategist and technical team.
• Reliable hourly pay plus a performance bonus for each qualified call you book.
• An opportunity to develop your skills in international B2B sales and technology services.

The hourly rate, bonus amount, and qualification criteria will be discussed during the hiring process. We will agree in advance on what counts as a qualified call and when the bonus is payable.

How to Apply

Send your CV or LinkedIn profile with a short description of your relevant experience. Please mention which channels you have used and what results you personally achieved.

Include your answer to this short task:

You are contacting the CTO of a software company. What specific information would you look for on their LinkedIn profile or company page to personalize your opening message? Write one example opening sentence in English based on a hypothetical finding.

Shortlisted candidates will be asked to provide a brief, approximately one-minute video or audio introduction in English. No special equipment or professional editing is required.