Senior Implementation & Engagement Manager

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.

As a Senior Implementation and Engagement Manager, you will lead post-sale success and retention efforts for Ascertain’s most important partners. This role is ideal for someone with experience in healthcare technology, SaaS implementation, or healthcare consulting who’s ready to build a high-impact function from the ground up.

You will own end-to-end customer success after the initial sale: overseeing pilot delivery, driving change management and adoption, and ensuring long-term retention and expansion. You’ll work directly with care management and revenue cycle teams to make sure our platform integrates smoothly into their daily workflows, delivering real, measurable value.

You will manage end-to-end deployments, from initial implementations to ongoing customer success initiatives and onboarding for future products. You’ll partner closely with Sales, Product, Engineering, and Marketing to ensure each deployment delivers measurable impact, provides clear ROI metrics for go-to-market decisions, and sets the stage for seamless adoption of our offerings.

This is a hands-on, high-ownership role for an operator who is comfortable in ambiguity and focused on reducing it. You use data to drive decisions and turn complex workflows into clear, repeatable systems. You’ll help define our partner success strategy, build scalable SOPs and playbooks, and shape the partner experience.

This position is remote with up to 25% travel to support customer implementations and key deployments.

• Own the Client Relationship: Serve as the primary client lead during implementation. Conduct stakeholder interviews, align on workflows, and maintain alignment with operational and executive stakeholders. Provide clear updates on progress, surface risks early, and ensure strong coordination through go live and early adoption.

• Lead Solution Deployments: Oversee customer onboarding (planning, configuration, testing, training, go-live, support) with clear project plans, milestones, and risk mitigation.

• Leverage Impact Metrics: Use established KPIs (e.g., time saved, turnaround reduction) to demonstrate ROI and support customer expansion strategies.

• Collaborate with Commercial. Upsell and cross sell new products to established customers; and then develop a scalable customer-success framework (onboarding, training, support, upsell).

• Develop a targeted (by customer type) customer-success framework (onboarding, training, support, upsell) and required materials (role-based meeting template)

• 5 to 7 years of experience in healthcare, including provider, payer, or healthcare technology environments

• 4+ years of experience leading healthcare IT or SaaS implementations with direct ownership of delivery

• Proven track record scaling complex, multi-stakeholder implementations and delivering quantifiable results.

• Exposure to customer-support workflows and tools to bridge the gap between implementation and ongoing support.

• Previous startup experience preferred.

• Data-Informed Operator: Leverage metrics and insights to demonstrate customer ROI and identify opportunities for account growth.

• Clear Communicator: Translate complex insights into clear recommendations for executives, customers, and internal teams.

• Customer-Centric Leader: Build trusted relationships, proactively address risks, and drive retention and expansion.

• Execution-Oriented: Plan and manage projects end-to-end—setting milestones, coordinating stakeholders, and mitigating risks.

• Hands-On & Adaptable: Thrive in a fast-paced startup environment, balancing strategic leadership with practical problem-solving and customer support.

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