Head of Sales Strategy and Operations

Courier Health • New York, NY

8d • $245,000 - $275,000 • Onsite

About The Position

Courier Health is hiring a Head of Sales Strategy and Operations to build and run the commercial infrastructure supporting its growing sales organization. Reporting to the Chief Commercial Officer, this leader will own pricing and packaging, deal desk, territory and coverage, commercial analytics, planning cadence, enablement, and the systems behind those functions. The role connects Sales with Product, Product Marketing, and Finance, and will establish frameworks and operating practices that shape how Courier Health goes to market.

Requirements

• 10+ years of experience in sales strategy, revenue operations, commercial strategy, or management consulting.
• At least 3 years leading the function at a high-growth B2B software company.
• Hands-on experience building pricing and packaging, deal structuring, territory design, and commercial analytics.
• Exceptional analytical ability, including the ability to derive insights and communicate them clearly to executive audiences.
• Demonstrated ability to build processes that teams adopt and sustain without slowing sales.
• Strong understanding of enterprise sales dynamics, including long sales cycles, multiple stakeholders, and procurement.
• Credibility with executives and willingness to challenge them when the data supports doing so.
• Comfort working independently across strategic frameworks and detailed analysis, including building models.
• Excellent written and verbal communication, particularly translating commercial data into actionable recommendations.
• Comfort with autonomy and ambiguity in an early-stage company.

Nice To Haves

• Experience in life sciences, healthcare, or health tech.
• Experience building a deal desk from scratch.
• Experience partnering closely with Product and Product Marketing on positioning, launches, and competitive intelligence.
• Deep knowledge of Salesforce and the modern commercial stack, including CPQ, forecasting, and enablement tools.

Responsibilities

• Own and evolve pricing and packaging as the product develops, including determining the value of new capabilities.
• Build and operate the deal desk, including deal structure, terms, approval processes, and partnership with sellers on key opportunities.
• Develop segmentation, territory design, account prioritization, and capacity planning to guide hiring and sales coverage.
• Partner with the Chief Commercial Officer and executive team on target markets, use cases, and commercial models, and translate decisions into actionable sales plans.
• Establish the sales operating rhythm, including pipeline reviews, forecasting, target setting, and business reviews.
• Define and consistently measure commercial metrics, including pipeline health, conversion, sales cycle length, win/loss, segment performance, and productivity.
• Own commercial systems and data, including CRM strategy, sales workflows, data standards, and seller-enabling tools.
• Partner with Finance on forecasting and provide analysis of the drivers behind commercial results.
• Build sales onboarding, playbooks, methodology, and competitive resources to improve seller effectiveness.
• Create a regular feedback channel from Sales to Product and Product Marketing, sharing deal patterns, loss reasons, unmet needs, and market intelligence.
• Ensure ICPs, positioning, and launch readiness reflect activity and feedback from live deals.

Benefits

• 100% paid employee health benefit options, including medical, dental, and vision.
• 401(k) with employer-funded match.
• Unlimited vacation.
• Commuter benefits.
• Paid parental leave.
• Catered lunch on Fridays.
• Wellness stipend.
• Equity.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed