Outbound SDR (Freelance)

PolandRemotemid

SalesSales Development Rep

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Quick Summary

Key Responsibilities

Run high-volume cold calls into assigned target lists. Open conversations, handle gatekeepers, and identify key decision-makers.

Requirements Summary

Apply qualification criteria defined per project, hand off qualified meetings to the relevant founder or sales lead, and disqualify cleanly when there's no fit.

Technical Tools

SalesSales Development Rep

Red Sky is a Polish venture studio. We build startups from scratch with our partner fund Tar Heel Capital Pathfinder, take them from idea to first revenue to exit - most recently PlumResearch. To accelerate outbound across selected portfolio projects, we're hiring a freelance Outbound SDR with a strong cold-calling instinct.

You'll work alongside our GTM team on 1-2 specific portfolio projects at any given time - startups and services operating in B2B SaaS, recruitment, fintech, maritime tech, and adjacent spaces.

Responsibilities

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Working business English (deal-breaker): You can run a sales call with an English-speaking founder or executive without slowing down or hiding behind a script. Native Polish, English that holds up under live pressure. No need for BBC accent, though.

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B2B-curious mindset: You don't need a B2B sales background - but you should be ready to drop the high-pressure scripted close and learn a more consultative approach. B2B founders don't respond to the same playbook as travel customers.

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Genuine interest in startups: You find new companies, technology, and venture-building interesting and pick things up fast. Prior exposure to startups, tech, or B2B SaaS is a plus, not a requirement.

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Self-starter: Most call-center work is heavily managed. This is the opposite. You'll plan your own day, hit your weekly numbers, and flag blockers without being asked. If that sounds like freedom rather than chaos - good.

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Tech-comfortable: Fast on a CRM, LinkedIn (Sales Navigator a plus), and outreach tools. New tool drops, you figure it out.

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Availability: 15–20 hours per week, with most calling during core business hours (10:00–15:00 CET) - that's when targets actually pick up.

What We Offer

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✓Real career upgrade: You'll be calling founders and B2B operators about meaningful business problems, with the time and judgment to actually have a conversation - not rush through a script.

✓Skill set that travels: You'll leave with B2B SDR experience, consultative sales chops, and startup-world fluency - three of the most transferable skills in tech sales. Whatever you do next, this CV bullet sells itself.

✓Path to core team: If this works out, the door is open to full-time as our portfolio scales. This is a freelance gig with a runway - not a one-off task.

✓Real autonomy: No one listening in on your calls, no daily script-quota theater. We set the target and the brief; how you hit it is your call.

✓Direct work with the people doing the work: Founders, GTM, sales leads - not layered through middle management. You'll see how serious startups actually run.

✓Useful network as a byproduct: You'll meet a lot of founders, operators, and investors as part of the role. Whatever comes next for you, that's a network worth having.

✓Flexibility: 100% remote, freelance, plan your own hours within the core calling window (10:00–15:00 CET).