Senior Upwork Sales Specialist & Bidder

Description:

Lead client acquisition on Upwork and similar freelance marketplaces to secure mid-to-large digital projects and long-term/retainer contracts. Craft strategic, high-converting proposals, manage bidding and pricing strategy, and coordinate with internal technical teams to deliver compelling, accurate scopes and timelines.

Key responsibilities:

• Lead end-to-end Upwork/freelance marketplace sales: opportunity discovery, proposal writing, pricing strategy, and negotiation for mid-to-large projects.
• Create tailored, high-converting proposals and cover letters that highlight technical capabilities and commercial value.
• Perform client discovery and consultative selling; manage negotiations to secure long-term engagements.
• Collaborate with technical teams to convert requirements into deliverables, estimates, and realistic timelines.
• Manage CRM/pipeline, track win rates, revenue metrics, and prepare basic reports/analytics.
• Represent the company with a polished, premium brand voice when communicating with senior stakeholders in USA/UK markets.
• Optimize bids to improve win rate, average contract value, and client retention.

What we’re looking for

• Must-have: Proven experience winning high-value projects on Upwork or comparable freelance marketplaces with documented success and strong client feedback.
• Exceptional proposal-writing skills: persuasive copy, clear scope definition, and commercial acumen to price premium services.
• Strong understanding of software development lifecycles, web and mobile technologies, and digital advertising campaign structure.
• Expertise in client discovery, consultative selling, and negotiation for long-term/retainer contracts.
• CRM and pipeline management skills; experience with Upwork flow, spreadsheets, and basic reporting/analytics.
• Excellent written and spoken English; polished communication for senior stakeholders in USA/UK.
• Ability to collaborate with technical teams and manage multiple time zones.


• Preferred: Professional portfolio of successful proposals and client references; 4+ years marketplace bidding/sales experience with at least 2 years securing mid-to-large digital projects.