AI-Driven Outsourcing Sales Executive

Jobtailor; Boston (MA); On-site; USD 150,000 - 230,000; Full time

Job summary

Ampliwork is seeking an experienced enterprise sales leader to own full sales cycles for outsourcing and AI-driven automation solutions. You will co-sell with global consulting partners, build executive relationships, and translate ROI models into credible business cases for finance.

You will collaborate with Pre-Sales and Product to scope deployments, engage VMO and procurement leaders, and shape commercial terms with senior executives.

Qualifications

• 5–10 years selling outsourcing or managed-services contracts at a tier-one services firm.
• Proven track record closing multi-year outsourcing deals worth millions.
• Strong grasp of evaluating outsourcing vs internal or tech-driven options.
• Comfort navigating procurement, MSAs, SOWs, and vendor compliance.
• Technical curiosity to position AI agents against labor-arbitrage models.
• Sales discipline for complex, multi-stakeholder deals with C‑level buyers.
• Energetic, curious, and excited by how AI agents will reshape services.

Responsibilities

• Own enterprise sales cycles where buyers compare outsourcing to AI-driven automation.
• Co-sell with global consulting partners on combined advisory, implementation, and platform.
• Translate ROI models into AI agent business cases for finance defense.
• Partner with Pre-Sales and Product to scope agent deployments.
• Build relationships with VMO, procurement, and shared-services leaders.
• Shape commercial constructs alongside CEO and Operations.
• Represent Ampliwork at industry forums.

Skills

Outsourcing sales

Multi-year deals

C-suite selling

Procurement navigation

Vendor relations

AI/automation positioning

Curiosity & energy

Job description

Ampliwork is seeking an experienced enterprise sales leader to own full sales cycles for outsourcing and AI-driven automation solutions. You will co-sell with global consulting partners, build executive relationships, and translate ROI models into credible business cases for finance.

You will collaborate with Pre-Sales and Product to scope deployments, engage VMO and procurement leaders, and shape commercial terms with senior executives.