iScribeHealth is an AI-powered virtual scribe solution that helps healthcare providers efficiently document patient care and sync data with Electronic Health Records (EHR) systems. Founded in 2015, we are dedicated to reducing provider burnout and improving healthcare efficiency through cutting-edge AI and automation. Our platform streamlines workflows, enabling doctors to focus on patient care while ensuring seamless EHR integration. At iScribeHealth, we empower our employees to make a meaningful impact—both for themselves and the patients we serve.

The Director of Customer Success is a hands-on, high-energy leader responsible for owning the full post-sale client experience at iScribeHealth. Reporting directly to the COO, this role carries significant organizational weight—sitting at the intersection of operations and customer experience, and serving as the primary driver of everything that happens after a client signs. With direct leadership over a team ofImplementation Specialists and Account Managers, this role ensures seamless onboarding, strong physician adoption, and long-term client retention and growth. This is a player-coach in the truest sense: someone who leads from the front, traveling to client sites and working side-by-side with their team during onsite go-lives. As a key operational leader, the Director of CustomerSuccess will build, implement, and continually optimize scalable processes, develop a high-performing team, and serve as a trusted cross-functional partner—empowered to advocate for customers and drive accountability across Sales,Product, Operations, and Support when client outcomes are at stake. This individual will be instrumental in shaping the customer journey and contributing to company growth as iScribeHealth continues to scale itsAI-driven intelligence platform, bringing equal parts operational execution and people leadership, and building a culture where wins are celebrated, growth is expected, and every physician we onboard is set up to succeed.

Essential Duties and Responsibilities

People Leadership & Team Development

• Lead, mentor, and develop a team ofImplementation Specialists and Account Managers—maintaining an active presence in day-to-day operations while setting clear expectations, tracking performance, and creating individualized growth paths for each team member.

• Operate as a true player-coach—equally willing to lead a go-live alongside the team as to guide strategy, and always the first to step in when the team needs support in the field.

• Lead structured 1:1 and team meetings and meetups providing consistent feedback, removing blockers, and actively supporting individual development and performance and keep the team connected to companydirection and each other.

• Translate company objectives and strategic priorities into clear, actionable direction—ensuring every team member understands where iScribeHealth is headed, how their role contributes to that vision, and what success looks like at both the individual and organizational level.

• Deliver honest, timely feedback that challenges team members to grow, while fostering an environment where open dialogue, learning from mistakes, and continuous improvement are part of the team’s DNA.

• Actively coach employees toward career advancement within iScribeHealth, identifying strengths, building development plans, and advocating for internal growth opportunities.

• Lead corrective action and performance improvement processes when needed—navigating difficult conversations with professionalism, fairness, clear documentation, and a defined path forward.

• Conduct formal performance reviews on a consistent cadence, delivering balanced, evidence-based evaluations that set clear expectations and drive meaningful growth.

• Monitor team morale and culture health, gathering ongoing feedback and proactively surfacing concerns or opportunities to leadership before they become issues.

• Manage team operations and task accountability within ClickUp—modeling strong process discipline, maintaining real-time visibility into team workload and project status, and continuously refining workflows to improve how the team operates.

• Exercise sound judgment on escalation—knowing when to independently resolve team or client situations and when to bring in the COO or executive leadership.

Implementation Execution & Physician Adoption

• Own end-to-end implementation strategy and execution with an obsessive focus on physician adoption—defining what a successful go-live looks like, building the process to get there consistently, and holding the team accountable to that standard on every engagement.

• Drive and sustain a physician adoption rate of90% or above across all active client engagements—establishing clear targets,tracking progress rigorously, and intervening quickly and decisively when adoption falls short of expectations.

• Be present at onsite go-lives, training alongside the team, troubleshooting in real time, and modeling the energy andprofessionalism that sets the tone for every client launch.

• Build and continuously refine a streamlined, scalable implementation methodology that minimizes client disruption,accelerates time-to-value, and drives adoption from day one.

• Oversee concurrent implementation projects within ClickUp, strategically allocating team resources—employees and contractors—based on project complexity, geography, and client needs, and ensuring project timelines, milestones, and accountability are maintained with full visibility.

• Develop and maintain playbooks, checklists, training materials, and best practices that ensure consistency and quality across every implementation the team delivers.

• Partner with Go-to-Market (GTM) teams to ensure the Customer Success organization is fully prepared ahead of new feature releases and product rollouts—equipping the team with the knowledge, talking points, and training materials needed to confidently onboard clients and champion new capabilities in every client interaction.

• Bring client and field insights back toProduct and Engineering, ensuring real-world workflow challenges and adoption barriers are visible, prioritized, and addressed in the product roadmap.

• Establish and report on key implementationKPIs—including time-to-go-live, adoption rates, physician engagement scores, and client satisfaction—using data to continuously raise the bar and provide the COO with clear visibility into team and client performance.

Account Management & Client Retention

• Own a 100% net retention target—building account strategies, client relationships, and proactive engagement models that ensure every client renews, expands, and continues to realize measurable value from iScribeHealth’s platform.

• Direct the Account Management team in developing and executing strategies for client engagement, satisfaction, and renewal—ensuring each AM has the guidance, tools, and support they need to deliver exceptional outcomes throughout the client lifecycle.

• Partner closely with Account Managers on their most important client relationships—joining key conversations, co-owning escalations, and providing senior presence and strategic perspective on accounts that require an elevated level of engagement.

• Support the Account Managers during QuarterlyBusiness Reviews (QBRs) with key client stakeholders, presenting performance data, adoption outcomes, and strategic recommendations that reinforce iScribeHealth’s value and deepen long-term partnerships.

• Build proactive account strategies focused on reducing churn risk, identifying expansion opportunities, and deepening client partnerships across the portfolio.

• Serve as the voice of the Account Management Tteam and the customer across the organization—actively representing clientneeds and team priorities in cross-functional settings, and empowered to drive accountability with Sales, Implementation, Product, Operations, and Support when client outcomes require it.

• Echo client concerns and feedback through the appropriate leadership channels, ensuring systemic issues are visible to theCOO and broader leadership team, prioritized, and resolved rather than managed in isolation.

• Collaborate with Sales to identify upsell and cross-sell opportunities, aligning on renewal forecasting, expansion pipeline, and strategies for at-risk accounts.

• Act as the primary escalation path for theAccount Management team—stepping in on difficult client situations, de-escalating with confidence, and guiding the team through resolution in a way that preserves the client relationship and strengthens team capability.

Travel and On-site Presence

This role is built for someone who is genuinely energized by travel—not someone who tolerates it. The Director of Customer Success should be the person who books the early flight, stays the extra day to make sure a go-live lands exactly right, and is already looking forward to the next destination before the current one wraps. This is not occasional travel or regional coverage. This role carries an expectation of approximately 90% travel, consistent with what is expected of theImplementation team, and that level of commitment does not taper off after onboarding. Six months in, a year in—this person is still in the field, still present, and still energized by it.

The right candidate brings a proven trackrecord of high-volume travel and has built a lifestyle and career around it.They understand what it takes to be effective on the road—staying sharp,staying professional, and staying focused on the client even when the schedule is demanding. When the week calls for it, this individual will split their timebetween supporting Implementation go-lives and Account Management engagements, moving fluidly between both functions based on where the team and clients needthem most.

In the field, this leader is a visible, high-energy presence—delivering training, leading go-lives alongside the team, and representing iScribeHealth with the professionalism, adaptability, and composure that clients and team members alike can rely on. They lead by example in every client-facing environment, excel at real-time problem solving under pressure, and never leave a site until the job is done right.

Qualifications

• 7+ years of progressive leadership experience in Customer Success, Implementation, or Account Management within a SaaS or healthcare technology company.

• Demonstrated player-coach mentality—equally comfortable leading from the field and guiding team strategy, with a track record of active participation in client-facing delivery.

• Proven success driving and sustaining high physician or end-user adoption rates—with direct accountability for hitting aggressive adoption targets in a healthcare technology or clinical workflow environment.

• Demonstrated experience owning net retention targets and building account strategies that drive client renewals, expansion, and long-term satisfaction.

• Experience directly managing bothImplementation and Account Management teams with full accountability for performance, retention, and client outcomes.

• Strong understanding of EMR/EHR ecosystems, integrations, and healthcare workflows.

• Experience leading structured team operating rhythms—including regular 1:1s, team meetings, performance reviews, and corrective action processes.

• Demonstrated ability to coach, develop, and retain talent, with a history of building career paths and advocating for team members’ growth within the organization.

• Strong cross-functional communicator with the ability to represent customer and team needs across Sales, Product, Operations, and Support—influencing without authority and driving accountability across departments when client outcomes are at stake.

• Proficiency in ClickUp or similar project management platforms, with the ability to build and maintain workflows, reporting structures, and accountability systems that give leadership clear visibility into team and client performance.

• Comfort partnering with COO and CFO-level leadership on department strategy, budgeting, headcount planning, and compensation decisions.

• Excellent interpersonal and communication skills—able to build trust quickly, deliver direct feedback with empathy, and navigate difficult conversations with professionalism.

• Strong project management skills with the ability to oversee multiple concurrent implementations without losing sight of adoption outcomes and client satisfaction.

• Proven track record of extensive travel with the demonstrated lifestyle commitment to sustain approximately 90% travel on an ongoing basis.

• Experience developing and delivering training programs and leading change management initiatives preferred.

Next Steps:

At iScribeHealth, we assign specific attributes and characteristics to each role. This helps us identify candidates whose natural strengths align with the demands of the position—contributing to both job satisfaction and long-term success. Our goal is to ensure that employees feel confident and fulfilled in their roles, rather than feeling like they have to stretch themselves unnaturally every day to meet expectations. The survey includes only two questions and typically takes less than 10 minutes to complete.

For the second question, “Describe How YouShould Behave at Work,” please answer based on your behavior in your current or most recent role—not the role you’re applying for.
You can access the survey using the following link: iScribeHealth
Once the survey is completed email resume to recruiting@iscribehealth.com

Why Join Us?

• Opportunity to impact the future of healthcare technology and AI-driven solutions.

• Competitive salary and benefits includingMedical, Dental, Vision, HSA/FSA, Education Reimbursement, 401k with Matching.

• Collaborative, dynamic team environment focused on innovation and growth.

iScribeHealth is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability status, protected veteran status, or any other characteristic protected by law.