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Job Overview
Location
Remote
Job Type
Full-time
Category
Sales
Date Posted
January 17, 2026
Full Job Description
đź“‹ Description
- • Own the full LinkedIn outbound funnel—from deep-dive research to booked sales demos—at an award-winning digital agency that has powered 300+ startups and Fortune 500 brands since 2006.
- • Build laser-focused prospect lists using Boolean search, Reddit threads, Quora answers, Discord communities, and Sales Navigator to surface decision-makers who are actively wrestling with the exact problems Plum Tree Group solves.
- • Craft 5-step message sequences that read like one-to-one notes, not blasts: short, value-packed, pain-point-driven copy that earns replies and starts genuine conversations; leverage ChatGPT for speed, then layer on human nuance and industry insight.
- • Deploy and monitor LinkedIn automation tools (Lemlist, Expandi, or similar) safely and compliantly, ensuring daily send limits, warm-up protocols, and A/B tests keep deliverability—and your demo calendar—sky-high.
- • Run inbox triage like a pro: respond to objections within minutes, nurture lukewarm leads, disqualify poor fits fast, and shepherd qualified prospects to a locked-in calendar slot with our sales team.
- • Continuously optimize: track open, reply, and booking rates; iterate copy, audience segments, and campaign cadence weekly; share learnings in a living playbook that the entire revenue team can reuse.
- • Collaborate closely with sales, marketing, and RevOps to align messaging with live case studies, new product releases, and ABM plays for named Fortune 500 accounts.
- • Maintain a polished, authoritative LinkedIn profile that showcases thought leadership and attracts inbound inquiries from US-based C-suite executives in IT, e-commerce, and digital transformation.
- • Document every experiment inside GoHighLevel or the CRM du jour, ensuring clean data hand-offs and transparent reporting on pipeline influence and revenue attribution.
- • Bring a founder’s mindset: spot opportunities to test new channels (Slack communities, Twitter DMs, niche forums) and pitch mini-campaigns that could unlock the next $1M in ARR.
🎯 Requirements
- • 2+ years of hands-on LinkedIn outreach, outbound SDR, or lead-gen experience in a B2B tech, SaaS, or digital-agency environment
- • Proven ability to book 15–25 qualified demos per month via cold LinkedIn sequences; metrics and referenceable results required
- • Expert-level command of LinkedIn Sales Navigator plus at least one automation platform (Lemlist, Expandi, Zopto, etc.)
- • CRM fluency: day-to-day experience with Salesforce, HubSpot, Zoho, or GoHighLevel (GHL strongly preferred)
- • Exceptional short-form copywriting skills—your messages get >40% open and >15% positive reply rates
- • Nice-to-have: Account-Based Marketing (ABM) campaign design for enterprise logos and/or familiarity with AI prompt engineering for rapid message variant generation
🏖️ Benefits
- • 100 % remote-first culture—work from anywhere with a stable internet connection and flexible hours that fit your life
- • Competitive base salary plus uncapped performance bonuses tied to every demo that converts to closed-won revenue
- • Annual learning stipend for courses, conferences, or certifications in sales tech, copywriting, or AI tools
- • Home-office setup allowance: latest MacBook or PC, second monitor, noise-canceling headset, and standing desk on us
- • Opportunity to shape the outbound playbook of a 17-year-old agency that already counts Google, Salesforce, and AWS as partners
Skills & Technologies
About The Plum Tree Group, Inc.
Chicago-based digital commerce and technology consultancy founded in 2004. The firm builds, integrates, and optimizes Magento e-commerce sites, ERP systems, and custom web applications for mid-market brands and manufacturers. Services span strategy, UX design, implementation, hosting, and ongoing support across B2C and B2B channels.
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