Senior Upwork Sales Specialist & Bidder

About the role

We are looking for a Senior Upwork Sales Specialist & Bidder to lead client acquisition on Upwork and similar freelance marketplaces. You will secure mid‑to‑large digital projects and long‑term retainer contracts by crafting high‑converting proposals and coordinating with internal technical teams.

Key responsibilities

• Identify and pursue opportunities on Upwork and other freelance platforms, from discovery to negotiation.
• Write tailored, high‑impact proposals and cover letters that showcase technical capabilities and commercial value.
• Conduct client discovery, consultative selling, and negotiate long‑term engagements.
• Collaborate with technical teams to translate requirements into deliverables, estimates, and realistic timelines.
• Manage CRM/pipeline, track win rates and revenue metrics, and produce basic reports/analytics.
• Represent the company with a premium brand voice when communicating with senior stakeholders in USA/UK markets.
• Optimize bidding strategies to improve win rate, average contract value, and client retention.

Required profile

• Proven track record of winning high‑value projects on Upwork or comparable freelance marketplaces, with strong client feedback.
• Exceptional proposal‑writing skills, persuasive copy, clear scope definition, and commercial acumen.
• Strong understanding of software development lifecycles, web and mobile technologies, and digital advertising campaign structures.
• Experience in client discovery, consultative selling, and negotiation for long‑term contracts.
• Proficiency in CRM and pipeline management, Upwork workflow, spreadsheets, and basic reporting/analytics.
• Excellent written and spoken English, able to engage senior stakeholders in USA/UK.
• Ability to collaborate across time zones and work remotely.

Required skills

• Upwork platform
• CRM systems
• Spreadsheets
• Software development lifecycle
• Web technologies
• Mobile technologies
• Digital advertising campaign structure
• Basic reporting and analytics