Strategy Jobs in Boston, MA

About Connie Health

Connie Health is the next-generation Medicare platform using AI plus local expertise to help seniors save money and get better care. Fresh off a Series B from top-tier investors, we are scaling fast and building the operational backbone that lets our advisors and growth teams move quickly and confidently.

The Role

This is a ground-floor opportunity for a recent graduate who loves working with data and bringing order to fast-moving operations. Reporting to the Director of Sales Operations, you will be the analytical and operational engine behind our sales team. You will turn raw data into clear reporting, help plan and manage advisor staffing and schedules, and tighten the systems and workflows that keep the team running. You will learn how a high-growth revenue organization actually works, with direct exposure to sales leadership and a clear path to grow into a senior analyst or operations role. As a company built on AI plus local expertise, we expect you to lean on AI tools to work faster and bring ideas for where automation can take manual work off the team's plate.

What You’ll Do

• Build and maintain reporting. Own recurring dashboards and reports across the sales funnel, including pipeline, conversion, productivity, and retention, so leaders always know how the business is performing.
• Turn data into insight. Pull, clean, and analyze data to answer questions from sales leadership; surface trends and flag what is working and what needs attention.
• Support workforce management. Help plan and maintain agent schedules, track staffing levels against plan, and monitor shift coverage so the team is properly staffed day to day and ready for seasonal surges like the Annual Enrollment Period (AEP).
• Track capacity and utilization. Monitor call volume, agent utilization, and productivity against capacity, helping leaders spot coverage gaps early and plan hiring and scheduling ahead of demand.
• Put AI to work. Use AI tools to speed up your analysis, reporting, and process work, from drafting and cleaning data to summarizing trends and prototyping automations, and help the team find smarter, faster ways to operate.
• Keep the CRM honest. Maintain data hygiene in the CRM, audit for gaps and errors, and make sure the numbers everyone relies on are accurate.
• Improve the systems and workflows. Document and refine how the sales team operates, including lead routing, handoffs, and approval steps, and help identify where tools and automation can remove manual work.
• Support day-to-day operations. Help administer sales tools, troubleshoot process hiccups, and keep playbooks and trackers up to date.
• Prep for key meetings. Assemble the numbers and slides behind weekly performance reviews, staffing reviews, and forecasting discussions.
• Take on projects. Jump into ad hoc analyses and process improvements that help the team scale, because there is always something to build.

What You Bring

• Education and Experience. Bachelor’s degree, with 1-3 years of experience. Any major is welcome; we care more about how you think than what you studied.
• Comfort with data. Strong analytical skills, comfortable manipulating data and identifying actionable takeaways from data.
• Attention to detail. You catch the inconsistency in a spreadsheet that others miss and you care about getting the numbers right.
• Process and planning mindset. You naturally look for a cleaner, more repeatable way to do a recurring task, and you enjoy bringing structure to schedules and moving parts.
• AI-curious. You experiment with AI tools (ChatGPT, Claude, and similar) to work faster and smarter, and you are eager to learn how AI can streamline reporting, analysis, and operations.
• Clear communication. You can explain a finding simply, in writing and out loud, to people who are not analysts.
• Ownership and hustle. You take initiative, manage your time well, and thrive in an environment that moves fast and changes often.
• Bonus. Internship experience in operations, analytics, workforce management, consulting, or finance, or any interest in healthcare or insurance.

Why You’ll Want This Job

• Direct mentorship from the Director of Sales Operations and visibility with senior revenue leaders.
• A real seat in a high-growth, mission-driven startup helping seniors navigate Medicare.
• A clear runway to grow into senior analyst, sales operations, or strategy roles as the company scales.
• The chance to learn the full toolkit across analytics, workforce management, systems, and operations, not just one narrow slice.