Operations Specialist

Ascertain is building AI agents to automate the administrative work that burdens care teams. We are in major health systems and large specialty groups, saving hundreds of staff hours every week.

Our backers include Northwell Health, New York’s largest health system, and Deerfield Management, a leading healthcare investment firm.

Together, we’re on a mission to restore time, trust, and focus to the people who keep healthcare running. Our work is urgent — not because of startup timelines, but because our customers rely on us to drive financial resilience and operational clarity in a system under strain.

How we hire, onboard, and support our people has become one of the most important things we do. As the People & Operations Specialist at Ascertain, you'll own that work, starting with recruiting and onboarding, and you'll help run the company alongside our Operations leadership. Expect roughly two-thirds of your time on People Operations and the rest on broader company operations: culture and events, contracts and vendors, finance operations support, and the projects that come up as we scale.

This is a hands-on, cross-functional role that requires strong organizational skills, sound judgment, and the ability to manage competing priorities independently. You'll work closely with Operations leadership, hiring managers, and employees across the company to keep processes moving, solve problems, and ensure nothing falls through the cracks.

We're looking for someone who thrives in a fast-paced environment, takes ownership from start to finish, and enjoys improving how things work. You might be a People Operations or recruiting coordinator ready for broader scope, an executive assistant who has kept a senior leader's world running, or an operations generalist who has handled HR alongside events, vendors, and budgets. What matters most is that you are organized, ambitious, and want to learn how a company runs end to end.

People Operations

• Own day-to-day recruiting operations
  , including candidate pipeline management, resume review, recruiter screens and behavioral interviews with clear, structured feedback to hiring managers, interview scheduling, assessments, background checks, employment verification, and offer logistics.

• Drive proactive candidate sourcing
  , building targeted candidate lists, conducting cold outreach, engaging prospective candidates, and maintaining a strong pipeline of qualified talent.

• Conduct candidate interviews, including initial recruiter screens and behavioral interviews, evaluating qualifications, experience, communication skills, and alignment with role requirements, and providing clear, structured feedback to hiring managers.

• Own onboarding and the employee lifecycle
  , from offer acceptance through new hire orientation, including documentation, equipment, system access, onboarding schedules, and follow-up. After onboarding, you manage employee changes, PTO and leave, performance review cycles, and offboarding.

Company Operations (shaped around your strengths)

• Shape company culture and events
  , planning team gatherings, offsites, and retreats, and building the rituals that make new and existing employees feel part of the company.

• Manage contracts and vendors
  : keep agreements, renewals, and vendor documentation organized, prepare contracts for review, and flag key terms and deadlines before they become problems.

• Support our Finance team on vendor invoices, bill approvals, expense follow-up, and audit-ready records.

• Improve operational processes and systems
  , maintaining accurate records and reporting, analyzing data, and using spreadsheets, AI tools, and automation to increase efficiency and support decision-making.

• In…