Director of Revenue Optimization

Sales

Director of Revenue Optimization

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Job Category: Sales
Requisition Number: DIREC018761

Director of Revenue Optimization - SoftWriters

More than a technology company.

Empower LTC Pharmacies. Save Lives. Build the Future of Healthcare Technology.

About SoftWriters

SoftWriters develops innovative IT solutions that empower long-term care (LTC) pharmacies to deliver life-saving medications more efficiently and accurately. As a voted top workplace in Pittsburgh, we combine meaningful work with a collaborative culture where your contributions directly impact patient care.

The Opportunity

We'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 Do

Revenue 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 For

Required:

• 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 Here

Meaningful 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

Our Values in Action

• Innovators, Thought Leaders, Teachers
• Accountability and Ownership
• Customer-Centric
• Unyielding Integrity
• One Team, Family Spirit

Ready to Apply?

Join a team where your leadership drives meaningful impact in healthcare technology. We’re looking for someone excited to transform revenue organizations through data, AI, and operational excellence.

Note: No visa sponsorship. Hybrid Pittsburgh required.

SoftWriters, Inc. is an equal opportunity employer. All qualified candidates will receive consideration for employment without regard for race, color, religion, gender, sexual orientation, national origin or citizenship status, age, disability, genetic information or veteran status.

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