Head of Sales

Acclaim•Pittsburgh, PA

10h•Remote

About The Position

The Head of Sales is responsible for building pipeline through partnerships, market engagement, and early customer programs for the Overtime.ai platform. All qualified opportunities and revenue generated through this role are credited to the Sales organization and count toward the Head of Sales’ pipeline and quota. The role reports to the CEO and is tightly aligned with Sales on priorities, pipeline development, and field execution.

Requirements

10+ years in enterprise software, fintech, or receivables management
Experience building partnerships or new revenue channels
Experience in healthcare partnerships or go-to-market strategy
Strong communication and industry presence
Comfortable working across teams without direct authority

Responsibilities

Build pipeline through partnerships, industry relationships, and targeted outreach
Develop early-stage opportunities and transition them into the sales pipeline
Support new channels that strengthen overall sales performance
Develop and manage strategic partners (platforms, integrations, industry relationships)
Create opportunities that drive distribution and embedded adoption
Act as a senior point of contact for key partners
Work closely with the Head of Sales on key opportunities
Support early deal shaping, use cases, and positioning
Participate in select sales cycles as needed
Ensure smooth handoff of opportunities to Sales for execution and close
Build and manage beta and pilot programs
Identify the right early customers and use cases
Drive conversion from pilot to paying customer in coordination with Sales
Build relationships across agencies, healthcare, and financial services
Represent Overtime.ai in the market and at industry events
Identify new use cases and opportunities
Partner with Sales on target markets and priorities
Align with Marketing, Product, and Operations
Provide market feedback to improve positioning and execution