Director of Revenue Optimization - SoftWritersThe OpportunityWe're seeking a
Director of Revenue Optimization to join our growing team and help shape the future of healthcare technology. In this role, you will architect and operationalize an AI-native commercial operating model that drives predictable revenue growth, enhances forecast confidence, strengthens pipeline visibility, and delivers measurable customer value across the organization.
Location: Hybrid - Pittsburgh, PA (Core office days: Tuesday, Wednesday, Thursday)
Reports to: Chief Revenue Officer
What You'll DoRevenue Operations Leadership- Build scalable commercial processes across the full customer lifecycle
- Establish operational rigor across pipeline management and forecasting
- Create unified KPI definitions and reporting standards
- Develop operating cadences (weekly forecasts, pipeline reviews, QBRs, exec reviews)
- Drive cross-functional alignment across Sales, Marketing, Customer Success, and Finance
- Build AI-native revenue workflows and automation strategies
- Continuously optimize sales processes
Forecasting & Pipeline Governance- Implement structured forecasting methodologies
- Standardize opportunity stage exit criteria
- Improve commit accuracy and deal inspection rigor
- Develop pipeline health scoring frameworks
- Monitor pipeline velocity, conversion rates, and slippage
- Deliver executive and board-level reporting
HubSpot CRM Governance & Data Quality- Define and enforce CRM governance standards
- Build data quality controls and required field frameworks
- Improve pipeline hygiene and reporting consistency
- Drive adoption across GTM teams
- Create automated alerts for data issues
- Develop dashboards and reporting environments
Value Engineering & Business Cases- Build ROI, TCO, and transformation models
- Standardize executive business case frameworks
- Quantify AI-driven productivity gains
- Support strategic deals with financial analysis
- Partner with Product Marketing on value metrics
- Develop executive-ready narratives (CFO, COO, CIO level)
Commercial Analytics & Revenue Intelligence- Develop dashboards and KPI scorecards
- Build pipeline health and forecast models
- Analyze funnel conversion and revenue drivers
- Create predictive insights (churn, expansion, deal risk)
- Scale analytics with Commercial Data Analyst
- Introduce AI-assisted forecasting and scoring
AI-Native Commercial Transformation- Identify AI automation opportunities
- Improve seller productivity with AI workflows
- Standardize commercial intelligence processes
- Develop AI-enabled sales playbooks
- Support modern GTM tech adoption
- Align processes with transformation positioning
Cross-Functional Alignment- Align Product Marketing with value engineering
- Support Marketing with attribution and insights
- Partner with Finance on planning and forecasting
- Enable Sales & Account Management with data insights
- Deliver executive and board-ready reporting
What We're Looking ForRequired:- 8-12+ years in Revenue Operations, Sales Ops, Commercial Strategy, or similar leadership roles
- Experience in SaaS or enterprise software environments
- Proven success scaling operations in high-growth companies
- Expertise in forecasting, pipeline governance, and revenue analytics
- Strong CRM and dashboard/reporting experience
- Experience with data governance frameworks
- Experience supporting enterprise sales and executive stakeholders
- Financial modeling expertise
- Ability to travel as needed to support business and client requirements
- Executive-level presentation development
Preferred:- Experience in AI, automation, or operational transformation
- Value engineering or consulting background
- ROI/TCO modeling experience
- HubSpot administration/architecture experience
- Board-level forecasting and reporting exposure
- Experience partnering directly with CROs and exec teams
Why You'll Love Working HereMeaningful Work: Direct impact on patient safety and pharmacy operations
Modern Work Environment: New, high-tech office on the North Shore waterfront
Recognized Top Workplace: Consistently voted one of Pittsburgh's best
Work-Life Balance:- Hybrid flexibility
- Remote-Work Bank
- Paid parking
- Birthday PTO + floating holidays
Comprehensive Benefits:- Competitive salary
- 100% paid parental leave
- 401(k) with match
Growth-Focused Culture:- Learning & development
- Cross-functional exposure
- Clear advancement paths
