Dropbox Director leading global sales enablement programs. Improving seller performance through analytics, training, playbooks, process design, and cross - functional revenue alignment.
About the role
- Sales operations leader scaling Phreesia’s healthcare SaaS revenue engine with Salesforce, forecasting, and AI. Leading planning, analytics, commercial systems, and team development across Phreesia’s growing solution portfolio.
Responsibilities
- Lead annual and quarterly sales planning across territory, capacity, quota, and compensation planning
- Design balanced territories and account segmentation, model headcount needs, and set quotas tied to forecast targets
- Partner with Finance and People teams on compensation plans
- Support go-to-market planning for new offerings
- Own the forecasting process and cadence for new business, renewals, and expansion
- Establish pipeline hygiene standards, stage definitions, and inspection rhythms
- Run weekly pipeline and forecast reviews with Sales leadership
- Partner with Finance on bookings-to-revenue reconciliation, campaign delivery pacing, and quarterly business reviews
- Build and maintain reporting for pipeline, win/loss, retention and renewal rates, upsell, rep productivity, and brand- and agency-level performance
- Present commercial insights to senior leadership and govern a single source of truth for commercial data
- Own the sales technology stack, including Salesforce, forecasting, enablement, data enrichment, and workflow tools
- Define and execute an AI roadmap using AI agents, predictive analytics, and intelligent automation
- Drive CRM adoption and data quality and design workflows that reduce manual seller effort
- Evaluate, pilot, measure, and scale emerging AI tools
- Run deal desk functions including pricing governance, approval workflows, proposal support, and order processing
- Improve quote-to-cash processes and own rules of engagement across Sales, Client Experience, and Market Development
- Scale sales best practices across outreach cadences, deal motions, and renewal plays
- Partner with Sales Enablement and Training to embed process changes and best practices
- Lead, develop, and mentor the Sales Operations team
- Serve as a trusted operating partner to senior Finance, Client Experience, and Sales leaders
Requirements
- Bachelor's degree required
- 10+ years of experience in sales operations, revenue operations, or commercial strategy
- 3+ years leading the function or a significant portion of it
- Prior people management experience
- Deep, hands-on expertise with Salesforce, including administration, reporting, and process design
- Experience owning forecasting, territory and quota planning, and sales compensation design within a quota-carrying sales organization
- Experience in media, advertising, point-of-care marketing, life sciences, or healthcare technology
- Familiarity with annually renewing or re-sold revenue models is a plus
- Strong analytical toolkit, including hands-on use of AI tools for analysis, forecasting, and workflow automation
- Experience with Salesforce Einstein/Agentforce, generative AI assistants, or similar tools
- High proficiency with Excel or Google Sheets
- Experience with SQL and Power BI or similar BI tools is preferred
- Ability to turn complex data into a clear, compelling narrative for executives
- Track record of scaling a commercial function with AI and automation
- Excellent cross-functional collaboration and communication skills
- Comfortable operating at strategic and hands-on levels
- Based in EST or CST in Canada or the U.S.
- Occasional travel required for client meetings, industry events, conferences, and team collaboration
Benefits
- Base salary and variable incentive
- Comprehensive Total Rewards package
- 100% remote work
- Home office expense reimbursements
- Monthly reimbursement for cell phone, internet and wellness
- Competitive compensation
- Flexible PTO and company holidays
- Variety of healthcare benefits for employees, families, and pets starting day one
- Generous top-up for parental leave benefits
- Continuing education and professional certification reimbursement
- Various offsite events and activities for team connection and team building
- Local in-person volunteer events and give-back programs
- Company-wide recognition tool with redeemable points and a catalogue of items
- Employee Resource Groups (ERGs)
- Accommodations available on request for candidates participating in the selection process
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