Role Description The Head of Revenue Development & Strategic Growth is responsible for building pipeline through partnerships, market engagement, and early customer programs for the Overtime.ai platform. This role works in close partnership with the Head of Sales to support deal development and accelerate revenue. 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. Qualifications - 10+ years in enterprise software, fintech, or receivables management - Experience building partnerships or new revenue channels - Strong communication and industry presence - Comfortable working across teams without direct authority Requirements - 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 Benefits - 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)

• Accounting & Controls: Own the monthly, quarterly, and annual close process for our brokerage operations within our CRM and subledgers • Operational Data & Reporting: Own the process of extracting, validating, and reconciling operational data from our CRM and other source systems into reliable financial outputs; Identify and resolve data discrepancies between operational systems and financial records; work cross-functionally with sales and operations teams to address root causes; Build and maintain management reporting that connects operational metrics to financial performance — revenue by carrier, by product, by channel; Track KPIs that give business unit leads visibility into the drivers of their financial results • Process Transformation & Automation: Identify and implement tools and workflows that drive efficiency in revenue recognition, month-end close, and KPI reporting. Leverage automations to ensure accurate and timely reporting; Build systems and processes that reduce manual effort and increase accuracy and speed across the finance function; Leverage Salesforce and other platforms to connect operational and financial data for more effective reporting and analysis • Financial Planning & Analysis: Assist with the annual budget and quarterly forecast processes for the Mortgage and Insurance BUs; Assist with the pricing analysis and modeling for the brokerages, including rate competitiveness, margin optimization, and industry specific economics • Team Leadership: Lead, mentor, and develop a team of financial analysts; Model the right culture — hands-on when needed, strategic when it counts

• Identify and maximize potential revenue opportunities for a portfolio of hotels • Gather data and conduct analysis of revenue potential generated by both transient and group travel • Make strategic decisions, communicate effectively with the on-property hotel team, and implement the revenue strategy • Daily review and management of Revenue Management System recommendations for room accommodation and rate inventory controls • Ensure group inventory is managed • Implement strategies on 3rd party internet channels ensuring parity in all distribution’s channels • Conduct group evaluation/displacement analysis as needed by hotel sales to determine impact on hotel RevPAR and overall spend in the hotel • Prepare weekly strategy reports for numerous hotels used during their strategy meetings • Prepare monthly sell strategy for 12-month booking window.

• Accountable for leading, guiding, & directing revenue cycle standard work. • Provides effective use of system resources to drive optimal revenue cycle outcomes and performance measures. • Enables regional level strategy to address internal or external business & regulatory issues; provides functional expertise & ensures fulfillment of performance & service standards. • Responsible for consistent operating performance & achieving financial goals. • Identifies, defines & solves complex problems that impact the management & direction of the business; Collaborates with Service Area, Regions & Health Ministries to ensure consistency & integration of strategy & operations. • Maintains awareness of new industry developments & standards. • Provides decision support, operations & / or optimization leadership focus.