Head of Sales

Why Join Us

Receivables management is a $20B+ market at an inflection point. Increasing regulatory complexity, rising operating costs, and declining effectiveness of legacy outbound models are driving demand for a modern, AI-first approach. Overtime.ai is the platform to define this next generation—combining voice AI, automation, and compliance-by-design to transform how the industry recovers debt while improving the consumer experience. This is a start-up leadership opportunity to shape go-to-market strategy, build a category-defining sales motion, and drive revenue in a market ready for disruption.

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.

• 10+ years in in enterprise sales, revenue development, or growth, with meaningful experience in healthcare markets
• 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

Revenue Development

• 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

Partnerships

• 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

Sales Collaboration

• 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

Beta and Early Customers

• 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

Market Engagement

• Build relationships across agencies, healthcare, and financial services
• Represent Overtime.ai in the market and at industry events
• Identify new use cases and opportunities

Alignment

• Partner with Sales on target markets and priorities
• Align with Marketing, Product, and Operations
• Provide market feedback to improve positioning and execution

• A team built from the collections industry — work alongside leaders with experience across third party collections, healthcare revenue cycle, and first party servicing.
• Opportunity to grow with the company — take on meaningful responsibility as the business expands.
• Fast moving environment with direct access to leadership — decisions get made quickly and ideas can move into execution without unnecessary layers.
• Build technology tied to real operational outcomes — focused on improving recovery performance, lowering operating costs, and creating a better consumer experience in regulated environments.
• Fully remote within the US
• 15 days PTO + all federal holidays + 3 sick days 
• Health insurance reimbursement (ICHRA)
• 401(k)
• Laptop provided by the company
• Participation in Employee Stock Ownership Plan (ESOP)