Outbound SDR (Freelance)

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. We supply the strategy, ICP, messaging, and infrastructure; you bring the dial tone and the judgment to know when a conversation is going somewhere - and when to move on. A heads-up before you scroll further: this is a calling-first role. Email and LinkedIn are part of the mix, but the phone is your primary lever. If you enjoy real conversations with strangers and don't flinch at gatekeepers, you'll be in your element. If you'd rather lean on automated sequences and hope someone clicks, this isn't for you.

Key Responsibilities

Outbound calling (your primary lever): Run high-volume cold calls into assigned target lists. Open conversations, handle gatekeepers, and identify key decision-makers. You will focus on building diverse relationships: from booking qualified sales meetings to securing strategic business partners and sourcing interviewees/guests for project-related content. Multi-channel outreach: Complement calls with personalized email and LinkedIn outreach to the same accounts, using sequences and messaging frames provided by the GTM team. Account research & enrichment: Take the target lists we provide and enrich them - verify decision-makers, dig up triggers (funding rounds, hiring signals, press mentions), and prepare context that makes each call count. Lead qualification & handoff: 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. Market signal feedback: Bring back what you hear - objections, repeating questions, where messaging lands and where it dies. Weekly sync with team GTM/PO; this is how we iterate fast on offer and approach. CRM hygiene: Detailed, timely records of every interaction in our system. No call without a note. What We're Looking For: Phone resilience and outbound chops: You've done real volume on the phone - B2B or B2C, doesn't matter. What matters is that you know how to open a call, work past gatekeepers, and stay sharp on call 101 when calls 1-100 went badly. 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. 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. 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. 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. Tech-comfortable: Fast on a CRM, LinkedIn (Sales Navigator a plus), and outreach tools. New tool drops, you figure it out. 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: 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. Compensation: Base retainer + performance bonus tied to qualified meetings booked. Flexibility: 100% remote, freelance, plan your own hours within the core calling window (10:00–15:00 CET). Recruitment Process: Fill the application Meet with People & Talent Business Partner & GTM (45min) Meet with Management Board (30min) Start cooperation