Head of Sales Strategy and Operations

Come Build with Us

We’re a NYC-based team that believes culture, craft, and customer obsession go hand in hand. We show up for each other the same way we show up for the people we serve. We’re an office-first company that values in-person collaboration 4 days per week because we believe the best work happens when you can collaborate and brainstorm together in the same room. If that sounds like your kind of place, we think you’ll love it here.

The Opportunity

Courier Health is signing faster than the function around our sales team can currently support. We exist to get patients faster, better access to life-saving therapies, and every program we win is another population we reach. What determines how fast that happens is no longer just how well we sell. I’s how we price, where we point the team, how the hard deals get structured, and whether leadership can see what’s actually working. This role owns that.

As Head of Sales Strategy & Operations, you’ll report to the Chief Commercial Officer and own everything that sits around the sales organization: pricing and packaging, deal desk, territory and coverage, commercial analytics, planning cadence, enablement, and the systems underneath all of it. You’ll also be the connection point between Sales and Product, Product Marketing, and Finance.

Most of this is still being written. The pricing frameworks, the approval model, the metrics leadership runs the business on, you’ll build them and then run them. If you’ve spent your career tuning someone else’s commercial engine, this is the seat where you design it. The calls you make in your first year become how Courier Health goes to market for the next five.

What You’ll Build

Pricing, packaging, and how deals get done. You’ll own what we charge, what’s bundled, and what a new capability is worth to a customer and keep evolving it as the product moves. Underneath that, you’ll build the deal desk: structure, terms, approvals, and real partnership with sellers on the opportunities that matter most. Done right, the framework makes deals move faster, not slower.

A coverage model that scales ahead of the pipeline. Segmentation, territory design, account prioritization, and the capacity math that tells us when to hire and where to aim. You’ll work with the CCO and executive team on where we play (which segments, which use cases, which commercial models) and turn those calls into plans the sales team can actually run. Then you’ll set the operating rhythm that keeps it honest: pipeline reviews, forecasting, target setting, business reviews.

A commercial picture leadership can act on. Pipeline health, conversion, cycle length, win/loss, segment performance, productivity - defined once, measured consistently, and reported in a form that changes decisions instead of describing them. You’ll own the systems and data underneath it too: CRM strategy, sales workflows, data standards, and the tooling that gives sellers their time back. You’ll partner with Finance on the forecast and own the read on why the numbers look the way they do.

A sales team that gets better every quarter. Onboarding, playbooks, methodology, and competitive resources built so sellers understand the customer’s problem, not just our product. You’ll also be the channel back: deal patterns, loss reasons, unmet needs, and market intelligence reaching Product and Product Marketing on a schedule rather than by accident. ICPs, positioning, and launch readiness should reflect what’s actually happening in live deals.

What Makes You Successful

• 10+ years in sales strategy, revenue operations, commercial strategy, or management consulting, including 3+ years leading the function at a high-growth B2B software company.
• Hands-on depth in pricing and packaging, deal structuring, territory design, and commercial analytics. You’ve built these, not inherited them.
• Exceptional analytical ability. You can get to the insight yourself and make it legible to an executive audience in one page.
• A track record of building process a team actually adopted and kept without adding drag to the sale.
• Strong command of enterprise sales dynamics: long cycles, multiple stakeholders, real procurement.
• Credibility with executives, including the willingness to disagree with one when the data says to.
• Comfortable moving between the framework and the spreadsheet. You’d rather build the model than wait for one.
• Excellent written and verbal communication, especially turning commercial data into a recommendation someone can act on.
• Comfortable with autonomy and ambiguity at an early-stage company.

Bonus points if you have:

• Experience in life sciences, healthcare, or health tech.
• Built a deal desk from scratch.
• Worked closely with Product and Product Marketing on positioning, launches, and competitive intelligence.
• Depth in Salesforce and the modern commercial stack - CPQ, forecasting, and enablement tooling.

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

Compensation

The annual salary range for the target level for this role is $245,000-$275,000 + equity + benefits, including medical, dental, and vision. Final compensation will be determined based on a variety of factors including relevant experience, interview performance, and internal equity.