Senior Director, Customer Success Enablement & Strategy

Enboarder

United States

Hybrid

USD 180,000 - 240,000

Full time

14 days+

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Benefits offered by this job

Health benefits (medical, dental, and

HSA contribution

401(k) matching

PTO & parental leave

Life and disability benefits

FSA & EAP

Tuition reimbursement & LinkedIn Learn

Hybrid/remote options

Dog-friendly HQ (US)

Weekly catered meals

Job summary

ModMed is seeking a Senior Director, CS Enablement & Strategy to define the vision and execute the digital transformation of our Customer Success Shared Services organization. This leader will oversee CS Transformation, AI/Automation, Internal Enablement, and PMO, shaping scalable operating models and governance across the function.

The role partners with Product, Support, Professional Services, Sales, and Marketing to align digital experience with product launches, while driving measurable

Qualifications

12+ years in CS Ops, Enablement, Transformation, or Tech Strategy; 7+ years in senior leadership.
Proven track record leading CS Ops, Enablement, PMO, and Technology teams in SaaS/enterprise.
Deep expertise in CS tech stacks: Gainsight, Salesforce, contact center platforms, LMS, WalkMe.
Hands-on AI/automation, RPA, workflow optimization experience.
Strong financial acumen with $3M+ operating budgets and software vendors.
PMP, Agile/Scrum, or Lean Six Sigma Black Belt certification.
Healthcare IT/HealthTech workflows expertise.
Experience architecting multi-pillar shared services during rapid scale or M&A.

Responsibilities

Lead operating model transformations and service innovation across CS units.
Govern CS tech stack roadmap and AI strategies for the customer lifecycle.
Oversee the CS PMO governance, resourcing, and launches.
Direct internal enablement, onboarding, leadership development, and change communications.
Partner with Product, Engineering, Support, Professional Services, and Marketing on DX.
Define enterprise metrics and telemetry to measure CS efficiency and ROI.
Build and scale a 30+ person CS Shared Services team.

Skills

CS Operations leadership

AI/Automation

Data analytics & telemetry

Cross-functional leadership

Budget management

Vendor management

Education

Bachelor’s degree in a relevant field

Advanced degree preferred

Tools

Gainsight

Salesforce

Genesys

WalkMe

LMS

Job description

Join the Team Modernizing Medicine

At ModMed, we’re not just building software—we’re reimagining the healthcare experience. Founded in 2010 by a practicing physician and a successful tech entrepreneur, we took a radically different approach: we hired doctors and taught them how to code. This \"for doctors, by doctors\" philosophy has allowed us to create an AI-enabled, specialty-specific cloud platform that places patients at the center of care.

A Culture of Excellence

When you join ModMed, you’re joining an award-winning team recognized for innovation and employee satisfaction. From our global headquarters in Boca Raton Florida, and extensive employee base in Hyderabad India, we are a team of 4,500+ passionate problem-solvers on a mission to increase medical practice success and improve patient outcomes:

Consistently ranked as a Top Place to Work

2025 Globee Business Awards: Gold Globee for “Technology Team of the Year”

2025 Black Book Awards: Ranked #1 EHR in 11 Specialties

Florida Venture Forum: Venture-Backed Company of the Year

We are growing fast, thinking big, and we are just getting started.

Ready to modernize medicine with us?

Job Description Summary:

The Senior Director, CS Enablement & Strategy is responsible for defining and driving the strategic vision, operational execution, and digital transformation of ModMed’s Customer Success Shared Services organization. This leader oversees four core functional pillars: CS Transformation & Operating Model Design, CS Technology & AI/Automation, Internal Enablement & Workforce Readiness, and the CS PMO.

In this role, the Senior Director will architect scalable customer operating models, govern enterprise CS technology platforms (e.g., Gainsight, SFDC, Genesys, WalkMe, LMS), and drive AI/automation adoption across the entire customer lifecycle. Additionally, the Senior Director leads through influence across executive partners in Product, Support, Professional Services, Sales, and Marketing to align digital experience (DX) requirements, accelerate product launch delivery, and ensure total organizational readiness.

Primary Duties & Responsibilities:

Operating Model Transformation & Service Innovation: Lead end-to-end customer operating model redesigns, workflow optimization, service innovation, process excellence, and M&A operational integrations across all Customer Success business units.

Technology Stack & AI Strategy: Direct enterprise CS tech stack governance and multi-year roadmap (Gainsight, SFDC, Genesys, WalkMe, LMS); pioneer AI, LLM, agent assist, predictive analytics, and RPA solutions to drive operational efficiency and support deflection.

PMO Governance & Program Delivery: Oversee the CS PMO to enforce disciplined program governance, resource coordination, release/product launch delivery, and continuous improvement initiatives across cross-functional projects.

Internal Enablement & Workforce Readiness: Direct internal learning & development strategies, new hire onboarding, release & role readiness, leadership enablement, and enterprise change management communications to empower CS teams.

Cross-Functional Executive Leadership: Partner closely with Product, Engineering, Support, Professional Services, and Marketing leaders to prioritize digital experience (DX) enhancements, align content roadmaps, and support major product launches.

Data-Driven Performance & Telemetry: Establish enterprise-wide operational metrics, business process analytics, and performance telemetry to measure CS efficiency, tool adoption, churn risk reduction, and ROI on technology investments.

Team Leadership & Scale: Build, mentor, and scale a high-performing 30+ person CS Shared Services team, leading through four direct reports (Directors/Sr. Managers) and fostering a culture of operational rigor, innovation, and accountability.

Requirements & Qualifications:

Bachelors Degree, Advanced Degree Preferred

12+ years of experience in Customer Success Operations, Enablement, Business Transformation, or Technology Strategy in SaaS, with at least 7+ years in a senior leadership role managing managers/directors

Proven track record leading CS Operations, Enablement, PMO, and Technology teams in a fast-paced SaaS or enterprise tech environment.

Deep expertise in CS tech stacks (Gainsight, Salesforce, Contact Center platforms, LMS, WalkMe).

Hands-on experience driving AI/automation, RPA implementation, and workflow optimization.

Strong financial acumen with experience managing $3M+ operating budgets and software vendors.

Superior executive presence and cross-functional negotiation skills.

PMP, Agile/Scrum, or Lean Six Sigma Black Belt certification.

Expertise in Healthcare IT / HealthTech workflows.

Proven experience architecting multi-pillar shared services organizations through rapid scale or M&A integration.

ModMed Benefits Highlight:

At ModMed, we believe it’s important to offer a competitive benefits package designed to meet the diverse needs of our growing workforce. Eligible Modernizers can enroll in a wide range of benefits:

United States

Comprehensive medical, dental, and vision benefits, including a company Health Savings Account contribution,

401(k): ModMed provides a matching contribution each payday of 50% of your contribution deferred on up to 6% of your compensation. After one year of employment with ModMed, 100% of any matching contribution you receive is yours to keep.