Meet Ascertain

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.

About the Role

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.

What You'll Do

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.

What Success Looks Like

In your first 90 days, you run recruiting logistics for our open roles without hand-holding, every new hire gets a complete, on-time onboarding, and nothing in the people queue goes stale.
By six months, you own at least one area beyond People Operations end to end, such as the company retreat, the contract and renewal tracker, or vendor bill follow-up.
By one year, the people processes you built run reliably without you in every step, and you are the person leadership turns to when something operational has to be done right.

What We're Looking For

2–5 years of experience in People Operations, recruiting, executive support, business operations, or another role where you owned a broad range of operational work. Experience at a fast-growing company or another demanding, high-standards environment is a plus.
Strong organizational, planning, and prioritization skills, with demonstrated ability to manage complex logistics, multiple stakeholders, competing deadlines, and high volumes of time-sensitive work with exceptional attention to detail.
Demonstrated ownership, judgment, and communication skills, with the ability to independently manage projects from start to finish, anticipate needs, solve problems proactively, and communicate effectively across all levels of an organization. You can point to something you ran end to end, and you are comfortable pushing work forward with people more senior than you.
Discretion and professionalism with sensitive information, including employee records, compensation, and personnel matters.

Comfort with contracts and numbers. You can read an agreement and pick out the terms that matter, and you are at ease reconciling a spreadsheet or checking an invoice. Procurement, bookkeeping, or executive support experience is a plus.

Strong technical and analytical skills, including proficiency with spreadsheets, operational systems, and AI tools, with the ability to use data and technology to improve processes. Experience with ATS and HRIS platforms is preferred.

How We Hire

After an initial conversation, finalists complete a paid, timed working session: a realistic set of operations problems that you solve and then present back to us. We think it is a better use of your time than a long take-home, and it shows us how you think.

Why Ascertain? Make a real difference: Your work will directly impact healthcare organizations and improve patient care. Join Ascertain in transforming healthcare with AI!

People & Operations Specialist