Senior Lead of Commercial Strategy & Operations

Commercial Strategy & Operations ("CSO") supports the President and his broader go-to-market function, including Employer Sales, Employer Client Success, Marketing, Clinical and Partnerships. CSO is responsible for:

• Commercial strategy (how we grow)
• Planning (resourcing, goals, compensation)
• Insights (how we’re doing and what we need to do differently next week/month/quarter)
• Process (like how we prepare for client meetings)
• Tools (like SFDC and AI tools for Commercial)
• Data (activities, contract details, customer health signals, and more)

This role sits within CSO and serves the Commercial organization, partnering closely with each member of the Commercial Leadership Team (head of Sales, head of Client Success, etc). Reporting to the VP of Commercial Strategy & Operations, the Senior Lead of Commercial Planning & Compensation exists to translate Lantern’s growth ambitions into the operating plan that the entire Commercial organization runs on.

You own the full planning and compensation cycle: OKRs, coverage and capacity models, compensation plans, quotas, and functional plans in support of those metrics. You ensure every Commercial team member understands what they are being asked to achieve, why the number is right, and exactly how they get paid for hitting it.

You will work closely with the Commercial Leadership Team and Finance, building and defending the analytical models that underpin Lantern’s growth strategy. You will also develop Board materials, maintain and improve long-term planning models, and be the person who catches the error before it surfaces.

You are both the strategic thinker who stress-tests the plan and the operator who makes sure commissions run accurately every quarter. Ultimately, your work directly shapes how a fast-growing company allocates its energy, how it reports progress to its board, and how effectively it delivers care to millions of members.

Own the annual Commercial planning cycle end to end: long-term growth ambitions, OKRs, Commercial design, and compensation planning process across all Commercial roles, in close partnership with Field Operations and Finance. Design and administer incentive compensation plans for Sales, Client Success, and Partnerships, and ensure commission policies and procedures are documented and maintained in real time.

Manage one direct report, a Commissions Analyst, and own the accuracy and timeliness of all commission payouts. Build, maintain, and improve long-term planning models from scratch, with clean logic, accurate numbers, and clear documentation. Develop Board and executive materials on Commercial strategy and performance vs. plan, including quarterly reporting and ad hoc deep-dive analysis.

Benefits:

• Paid Vacation
• Health Insurance
• Health Savings Account
• Dental Insurance
• Vision Insurance
• Paid Parental Leave
• Short & Long Term Disability
• Life and AD&D Insurance
• Commuter Spending
• Retirement Savings Plan

Qualifications:

• Gritty and hard-working, with the ability to operate in a dynamic, high-growth environment
• Deep analytical skills in Microsoft Excel with strong attention to detail
• Excellent problem-solving skills, even when the problem at hand is ambiguous
• Background in investment banking or management consulting
• 8+ years of relevant professional experience
• Highly organized, with the persistence to follow up until things are done and proactively communicate progress
• Strategic thinker who can articulate long-term value creation, not just operational discipline — able to unpack business drivers at the second, third, and fourth order
• Demonstrated experience running multiple Commercial annual planning and compensation planning cycles
• Prior experience working within healthcare or employer benefits
• Experience in business operations or sales operations
• Familiarity with a wide variety of sales compensation structures, particularly usage-based revenue models
• Strong PowerPoint skills, with the ability to build polished, high-quality slides quickly