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.
Requirements- 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)
Skills Required
- 10+ years 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 skills and industry presence
- Comfortable working across teams without direct authority
Acclaim AI Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Acclaim AI and has not been reviewed or approved by Acclaim AI.
-
Parental & Family Support — Parental leave is explicitly listed on the company’s Wellfound profile. Feedback suggests family support is part of the baseline perks communicated publicly.
-
Leave & Time Off Breadth — Generous vacation is highlighted on Wellfound. This points to broader time-off flexibility typical of startup-style packages.
-
Wellbeing & Lifestyle Benefits — Professional development and company events are called out on Wellfound. These signals indicate investment in growth and team connection beyond core benefits.
Acclaim AI Insights
What We Do
Acclaim is a voice-first AI customer experience (CX) platform purpose-built for regulated industries including banking, fintech, healthcare, and insurance. It provides enterprises with goal-oriented AI agents that go beyond conversation to deliver agentic solutions that solve end-to-end business problems—orchestrating and executing complete customer workflows from outreach through resolution. Acclaim's solutions transform human-driven CX processes into AI-powered ones that are continuously learning and improving. Our platform helps organizations delight with human-quality conversations, accelerate revenue-driving interactions, and safeguard their data by maintaining strict compliance across every customer channel—creating more seamless customer experiences while improving the productivity and satisfaction of human agents. Built on a privacy-first architecture with on-premises or private cloud deployment, Acclaim ensures every interaction is secure, compliant, and delivers results that speak for themselves.
