Generate enterprise B2B sales for custom software development and IT services across North America and LATAM. Responsibilities include outbound prospecting, executive discovery sessions in English and Spanish, value proposition development, proposal negotiation, pipeline management through contract signature, and account expansion. The role is fully remote, freelance, autonomous, and commission-only, with technical support from solution architects and engineering leaders.
Executive Summary
At Appspring, we engineer high-performance custom software solutions and build specialized engineering teams for scaling enterprises. To accelerate our commercial expansion across North America (USA & Canada) and LATAM, we are partnering with a Senior Freelance B2B Sales Executive with a proven, elite track record in the IT and Custom Software Development sectors.
This strategic opportunity is tailored for established, high-performing commercial professionals looking to capitalize on their industry experience and executive networks to generate significant additional revenue through an aggressive, uncapped commission structure.
Core Commercial Responsibilities:
- Targeted Outbound Prospecting: Strategically identify, engage, and qualify enterprise decision-makers (CTOs, VPs of Engineering, Chief Product Officers, and C-Suite Executives) utilizing multi-channel outreach strategies.
- Discovery & Value Proposition: Conduct high-level discovery sessions in English and Spanish, articulately positioning Appspring’s custom engineering capabilities and value proposition.
- Deal Structuring & Negotiations: Partner directly with our technical leadership to formulate, present, and negotiate high-ticket commercial proposals and service agreements.
- Pipeline Management: Drive complex sales cycles from initial outreach through contract signature with high conversion velocity.
- Strategic Account Expansion: Maintain relationship oversight on closed accounts to identify long-term upselling and cross-selling opportunities.
Senior Candidate Requirements:
- Professional Engagement: Strictly independent Senior Freelancers looking to integrate a high-yield, premium project alongside their existing professional activities. (Agencies or third-party representatives will not be considered).
- Industry Track Record: Minimum 5+ years of verified executive-level B2B sales success exclusively within Custom Software Development, Staff Augmentation, IT Consulting, or Enterprise Tech Solutions.
- Technical & Commercial Acumen: In-depth understanding of modern tech stacks, software development lifecycles (SDLC), and IT service models to conduct authoritative technical conversations with technical leadership.
- Bilingual Executive Fluency: Native/Bilingual proficiency in both English (C1/C2) and Spanish, required to lead C-level negotiations in both regions effortlessly.
- Sales Technology Proficiency: Advanced operational mastery of LinkedIn Sales Navigator, enterprise CRMs (HubSpot/Salesforce), and cold outreach infrastructure.
Commercial Framework & Support:
- Complete Operational Autonomy: 100% remote performance with total schedule flexibility, aligned with a senior independent consulting model.
- 100% Performance-Based Revenue (High-Yield Commission): An uncapped, highly lucrative commission percentage paid directly on every closed project/contract value, offering maximum earning potential with no income ceilings.
- Dedicated Engineering Pre-Sales Support: Our solution architects and technical directors participate directly in deep-dive technical meetings alongside you to ensure high deal-closing rates.
Similar Jobs
37 Minutes Ago
Artificial Intelligence • Fintech • Insurance • Marketing Tech • Software • Analytics
Investigates and processes commercial auto physical damage claims, determines coverage, assesses damage, establishes reserves, negotiates settlements, and maintains accurate claim documentation. The role communicates with insureds, claimants, agents, and internal teams; prepares or reviews damage estimates; identifies fraud and subrogation opportunities; and coordinates with appraisal and investigative units. A high school diploma and 1–2 years of experience are required, with claims experience preferred.
Marketing Tech • Mobile • Software
Own the full enterprise sales cycle for Vibes Connect and RCS Studio, from prospecting and discovery through closing six-figure deals. Generate outbound pipeline, manage forecasts, conduct solution demonstrations, translate technical API and messaging capabilities into business value, and build relationships with enterprise brands. Track performance in HubSpot, collaborate with stakeholders, and consistently exceed sales targets in a remote, fast-paced environment.
Top Skills:
APIsHubspotMmsRcsSms
Artificial Intelligence • Fintech • Insurance • Marketing Tech • Software • Analytics
Handles inbound calls and warm leads, consults customers on insurance needs, recommends appropriate property and casualty coverage, and converts prospects into policyholders. The role includes paid licensing and training, customer relationship management, sales closing, and compliance with state licensing requirements. Employees work remotely on assigned weekday and weekend schedules, using company-provided equipment and a dedicated wired internet connection.
Top Skills:
PcWired High-Speed Internet
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
