Director, Head of Sales Operations

Job Description: Shape the Future of Sales Operations at Phreesia Title: Director, Head of Sales Operations Team: Phreesia Network Solutions Location: Remote EST or CST in Canada or the U.S., with occasional travel required for client meetings, industry events, conferences, and team collaboration. Why This Role Exists Phreesia Network Solutions partners with pharmaceutical manufacturers, biotech companies, media agencies, and other life sciences organizations to activate patients and engage providers with personalized, privacy-safe communications at the moments that matter most in care. Our media programs are sold — and re-sold — every year, which means our commercial engine has to run with precision: accurate forecasts, clean pipeline data, well-designed territories and quotas, and sellers who spend their time selling. As Director, Head of Sales Operations, you will own that engine — and modernize it. You will be the connective tissue between Sales leadership, Finance, Marketing, Client Experience, and Client Solutions — turning strategy into operating cadence, data into decisions, and friction into process. You will scale the commercial operation with AI at its backbone, embedding AI-driven forecasting, insights, and automation across the sales workflow so the team can grow revenue faster than headcount. Reporting to the SVP, Finance & Commercial Operations, you will lead an established Sales Operations team and own the systems, analytics, and planning disciplines that allow the PNS sales organization to scale efficiently as we grow across PatientConnect, ProviderConnect, MediFind, and our expanding solution portfolio. What You’ll Spend Your Time Doing Lead sales planning and go-to-market design. You’ll lead annual and quarterly sales planning across territory, capacity, quota, and compensation planning — designing balanced territories and account segmentation, modeling headcount needs, setting quotas tied to forecast targets, and partnering with Finance and People teams on compensation plans that incentivize the right behaviors across new business, renewals, and upsell. You’ll also support go-to-market planning for new offerings, ensuring rules of engagement, coverage, and targets are in place at launch. Own forecasting and pipeline management. You’ll own the forecasting process and cadence, delivering accurate, defensible revenue forecasts across new business, renewals, and expansion for a business built on annually re-sold media programs. You’ll establish pipeline hygiene standards, stage definitions, and inspection rhythms; run weekly pipeline and forecast reviews with Sales leadership; and partner with Finance on bookings-to-revenue reconciliation, campaign delivery pacing, and quarterly business reviews. Turn commercial data into actionable insights. You’ll build and maintain the reporting suite for the business, including pipeline, win/loss, retention and renewal rates, upsell, rep productivity, and brand- and agency-level performance. You’ll deliver insights that shape strategy — identifying where we’re winning, where deals stall, and which therapeutic areas and agency relationships are growing — and present those insights to senior leadership. You’ll also define and govern a single source of truth for commercial data across systems. Scale systems, tools, and AI capabilities. You’ll own the sales technology stack — with Salesforce as the backbone, alongside forecasting, enablement, data enrichment, and workflow tools — including administration, roadmap, integrations, and vendor management. You’ll define and execute an AI roadmap for the commercial organization, deploying AI agents, predictive analytics, and intelligent automation to improve forecast accuracy, surface deal risk and next-best actions, automate non-selling work, and increase seller productivity. You’ll drive CRM adoption and data quality, design workflows that reduce manual effort for sellers and account teams, and ensure the clean, governed data foundation that AI-driven insights depend on. You’ll also evaluate emerging AI tooling with a practical eye — piloting quickly, measuring impact, and scaling what works. Improve deal support and commercial processes. You’ll run deal desk functions, including pricing governance, approval workflows, proposal support, and order processing in partnership with Legal, Finance, and Client Experience. You’ll continuously identify and remove friction across the quote-to-cash process and own rules of engagement across Sales, Client Experience, and Market Development. Scale sales best practices. You’ll identify what’s working across outreach cadences, deal motions, and renewal plays and scale those practices across the team to shorten sales cycles and maximize selling time. You’ll partner closely with Sales Enablement and Training, which is owned separately, to ensure process changes, tooling, and best practices are embedded in onboarding and ongoing coaching. Lead and develop the Sales Operations team. You’ll lead, develop, and mentor an established Sales Operations team spanning analytics, systems administration, and deal support, shaping the function’s structure as the business grows. You’ll serve as a trusted operating partner to the SVP, Finance & Commercial Operations, Client Experience, and Sales leadership, taking meaningful non-selling work off the plates of the sales team so they can focus on clients and revenue. What Makes You a Great Fit You will be a great fit if you are: Bring deep, hands-on expertise with Salesforce, including administration, reporting, and process design, and ideally have experience owning a broader revenue technology stack Have demonstrated ownership of forecasting, territory and quota planning, and sales compensation design within a quota-carrying sales organization Bring 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 Have a strong analytical toolkit, including hands-on use of AI tools for analysis, forecasting, and workflow automation, such as Salesforce Einstein/Agentforce, generative AI assistants, or similar Are highly proficient with Excel or Google Sheets; experience with SQL and Power BI or similar BI tools is preferred Know how to turn complex data into a clear, compelling narrative for executives Have a demonstrated track record of scaling a commercial function with AI and automation — identifying use cases, driving adoption, and measuring productivity impact Bring excellent cross-functional collaboration and communication skills and are comfortable operating at both strategic and hands-on levels in a fast-growing business We Do Have A Few Requirements To Check Bachelor’s degree required 10+ years of experience in sales operations, revenue operations, or commercial strategy, including 3+ years leading the function or a significant portion of it Prior people management experience Where You’ll Work This is a remote role, with the expectation that you’re based in EST or CST in Canada or the U.S. Occasional travel is required for client meetings, industry events, conferences, and team collaboration. Compensation & Rewards Base Salary: $240,000-260,000 USD or $200,000-230,000 CAD (depending on experience) inclusive of base salary and variable incentive. A comprehensive Total Rewards package designed to support your whole life — not just your work Who We Are: At Phreesia, we’re looking for smart and passionate people to help drive our mission of creating a better, more engaging healthcare experience. We’re committed to helping healthcare organizations succeed in an ever-evolving landscape by transforming the way healthcare is delivered. Our SaaS platform digitizes appointment check-in and offers tools to engage patients, improve efficiency, optimize staffing, and enhance clinical care. Phreesia cares about our employees by providing a diverse and dynamic work environment. We’re a five-time winner of Modern Healthcare Magazine’s Best Places to Work in Healthcare award and we’ve been recognized on the Bloomberg Gender Equality Index. We are dedicated to continuously improving our employee experience by launching new programs and initiatives. If you thrive in a culture of recognition, value inclusivity, professional development, and growth opportunities, Phreesia could be a great fit! Top-rated Employee Benefits: 100% Remote work + home office expense reimbursements Competitive compensation Flexible PTO + 8 company holidays Monthly reimbursement for cell phone + internet + wellness 100% Paid 12-week parental leave to our U.S. employees, as well as a generous parental benefit to our employees in Canada Variety of insurance coverage for people (and pets!) Continuing education and professional certification reimbursement Opportunity to join an Employee Resource Group. At Phreesia, we’re transforming the patient experience and giving healthcare organizations the capacity to do more—and we need smart, innovative problem-solvers to help us get there. Phreesians have a wide range of backgrounds—you don’t need to be a healthcare expert or a technology geek to succeed on our team. We’re looking for talented, diverse individuals who want to make a difference in healthcare.