The Senior Vice President, Commercial Operations leads the enablement engine behind RedSail Technologies’ growth. Reporting to the Chief Growth Officer, this leader unites Sales Operations, Sales Support, Sales Enablement & Training, Program Commercialization, the RedSail Advantage Solutions Project Management Office (PMO), and Clinical Services into one function that equips both Pharma Sales and Pharmacy Sales to win, launch, and grow. RedSail serves approximately 16,000 pharmacies, and its growth increasingly depends on pharma solutions powered by an engaged pharmacy network, a steady cadence of new product launches, and new-logo onboarding. This role builds the operating infrastructure, talent, and AI-enabled ways of working that make that growth repeatable and scalable, and leads with deep cross-functional partnership across Pharma Sales, Pharmacy Sales, Product, Marketing, Finance, Legal, and IT.
Key Duties
Commercial Operations Leadership
- Leads Commercial Operations as a single enablement function serving Pharma Sales and Pharmacy Sales; sets its vision, structure, and operating cadence, and establishes an integrated commercial operating model connecting sales planning, seller readiness, launch execution, onboarding, and ongoing program delivery.
- Serves as a strategic partner to the Chief Growth Officer and sales leaders across pharma and pharmacy sales, Connected Solutions, health systems, and expansion sales.
- Builds, leads, and develops a high-performing leadership team across Sales Operations, Enablement & Training, Program Commercialization, PMO, and Clinical Services; establishes shared priorities, clear responsibilities, and cross-functional handoffs, while strengthening leadership bench depth and succession.
- Builds a culture of collaboration within Commercial Operations and across the Growth organization; establishes shared planning and decision-making practices, promotes proactive information sharing and early partner involvement, and holds leaders accountable for cross-functional commitments and collective outcomes. Addresses siloed ways of working and resolves competing priorities constructively to advance shared Growth objectives.
- Contributes to Growth organization forecasting and annual planning with Finance.
AI Adoption & Commercial Productivity
- Leads adoption of AI tools across the commercial organization (i.e. Gong, Supademo), including prospecting, account planning, forecasting, call preparation, training, and program reporting.
- Sets adoption goals, measures productivity and revenue impact, and builds AI fluency across the team and the sales organization.
Sales Operations & Sales Support
- Governs CRM and sales systems (e.g., Dynamics, Salesforce, Monday.com) for data integrity, adoption, and usability; streamlines pre-sale to post-sale workflows.
- Directs forecasting methodology, pipeline management, and insights on bookings, win/loss, and rep performance for executive stakeholders.
- Partners with sales leadership on the annual quota and territory planning
- Collaborates with sales leadership, finance and HR on incentive compensation design and administration.
- Oversight of the activation process for connected solutions and pms ancillary solutions.
- Oversight of Hardware Sales and broader sales support, Account Processing and Customer Data Governance
Sales Enablement & Training
- Evolves a scalable training curriculum for pharma and pharmacy sellers, from onboarding and ramp through ongoing skills development.
- Ensures launch readiness for every new product and program, including positioning, quoting, enablement content, tools, and pre- and post-launch reinforcement.
- Partners with Sales Operations to identify performance gaps and ties enablement investments to productivity and revenue outcomes.
Program Commercialization
- Oversees commercialization, go-live execution, and post go-live operations for programs and services launched into RedSail’s pharmacy network and health systems.
- Directs program penetration goals, forecasting, and ROI tracking against program targets.
- Ensures compliance monitoring controls and success valuation protocols are in place, in partnership with Program Effectiveness and Legal.
RedSail Advantage Solutions Project Management Office (PMO)
- Scales the RedSail Advantage Solutions PMO to support a growing portfolio of product launches and new-logo onboarding; establishes standard intake, prioritization, governance, and status reporting.
- Drives cross-functional execution with Sales, Product, Development, Marketing, Finance, and Legal to deliver launch and onboarding milestones on time.
Clinical, Technical Services & Pharmacy Engagement
- Leads the clinical pharmacists, technical sales engineers and advisor teams that engage pharmacists and pharmacy staff pre and post sale to assist sales, activate, adopt, and deliver pharma and clinical programs and RedSail pharmacy solutions
- Builds and measures pharmacy engagement strategies that drive participation, utilization, and outcomes that power RedSail’s pharma and pharmacy solutions.
- Translates pharmacy-level performance into insights for pharma partners, pharmacy stakeholders and internal leadership.
Stakeholder Engagement & Reporting
- Leads external discussions with pharmacy owners and decision makers, i.e. Customer Advisory Board.
- Reports to senior leadership on key commercial metrics, including pipeline, bookings, program penetration, locations, patients, and transactions.
- Performs other duties as assigned by RedSail Technologies Growth management.
Education/Training
- Bachelor’s degree in Business, Healthcare, Life Sciences, or a related field OR the equivalent combination of education and relevant work experience. MBA or other advanced degree preferred.
- At least ten (10) years of professional experience in commercial operations, sales or revenue operations, sales enablement, or program commercialization, including senior leadership roles.
Required Work Experience/Skills
- Expert knowledge of commercial operations disciplines: CRM strategy, forecasting, pipeline management, territory and quota design, incentive compensation, and sales enablement.
- 8+ years leading multi-functional teams, including leaders of leaders, with a record of building and scaling teams in high-growth environments.
- 5+ years in healthcare, pharmacy, pharmaceutical, or health technology/SaaS commercial organizations.
- Demonstrated leadership of AI and sales technology adoption, with measurable gains in productivity and performance.
- Proven success designing onboarding and ongoing training programs for complex, multi-segment sales teams.
- Track record leading product and program launches, PMO functions, and cross-functional execution against P&L and ROI goals.
- Executive presence, strong analytical skills, and the ability to influence and align stakeholders at all levels, internally and externally.
Preferred Work Experience/Skills
- Expert understanding of the pharmacy ecosystem, including independent, chain, and health-system pharmacy, and pharmacy workflow.
- Advanced knowledge of pharma manufacturer commercial models, including patient support, adherence, pharmacy-based programs, and pharmacy or patient engagement channels.
- Experience leading or partnering closely with clinical teams.
- Advanced proficiency with Dynamics, Salesforce, Monday.com, Power BI or Tableau, and AI productivity tools.
- Experience in private equity-backed or acquisition-driven companies, including integrating teams and processes.
- Familiarity with Six Sigma or Lean methodology.
Compensation & Total Rewards
- The anticipated base salary range for this position is $225,000 - $240,000 annually. This position is also eligible for an Annual target bonus of 30%. Actual compensation will be determined based on factors including relevant experience, skills, qualifications, and geographic location. Target incentive earnings are based on individual, team, and/or company performance, subject to plan terms, eligibility requirements, and company policies. Incentive plan details will be provided upon hire. Actual compensation will be determined based on factors including relevant experience, skills, qualifications, internal equity, and geographic location.
- Benefits include paid time off, medical, dental, and vision insurance, a 401(k) with a 5% company match, a fitness bonus, professional development opportunities, and programs that support overall well-being
Work Location
- Remote or Hybrid at a RedSail Office o Spartanburg, SC o Irving, TX o Shreveport, LA o Oak Brook, IL o Cranberry Township, PA o Long Island, NY