Charles Weiselberg | HIPAA | Director of Customer Success

Recent appearance

Charles on Rebecca Novetsky's 'Next Hire' podcast.

Rebecca and I sit down for a chat about customer success, leadership, and why I should be your next hire on this episode of her wildly successful Spotify podcast.

Executive snapshot

Selected performance highlights.

A quick view of the outcomes most relevant to customer success leadership roles.

These numbers come from nearly a decade in healthcare SaaS. Retention in this space depends on trust, compliance knowledge, and follow-through. I earned these results as a lean team, often a department of one, owning the full post-sales lifecycle.

98%

Client retention across nearly a decade of healthcare SaaS customer success work.

$10M

ARR supported while running Customer Success as a department of one.

600+

Healthcare organizations supported at scale through onboarding, enablement, and compliance work.

95%

Customer satisfaction survey score maintained across customer-facing work over the course of my career.

Selected outcomes

Examples of leadership in practice.

These examples show how I approach customer adoption, operational scale, and cross-functional improvement when a team needs structure and follow-through.

In regulated healthcare, customer success goes beyond engagement metrics. You need to understand compliance workflows and earn trust from busy practitioners. The systems you build must scale without losing the personal touch that drives renewals.

At-risk account recovery

Stabilized a large franchise rollout and cut onboarding time by 25%.

When I joined AccountableHQ, our largest client was stuck. A major mental health franchise was not moving through HIPAA compliance as expected. I dug into the data, found the friction points, and reached out to each clinic directly. I invited them to live onboarding sessions. Usage went up. Meetings increased. Stagnation dropped.

Contacted each franchise location to build trust and reset the relationship.
Paired live onboarding with automated follow-up to keep momentum between calls.
Rolled out 150 franchise locations. Cut onboarding from 12 weeks to 9.

Voice of customer

Turned customer feedback into product movement.

I made customer feedback a standing topic in weekly product syncs. I documented recurring friction and pushed for prioritization based on what customers actually hit. This kept Product, Sales, and CS working from the same reality.

Operational leverage

Used systems to keep service personal.

I use automation to save human attention for the moments that matter most. That means implementation friction, at-risk signals, escalations, and expansion. This approach let me manage 600+ organizations and $10M ARR with lean resources.

Scale without headcount

Built the CS machine before building the team.

I wrote 35+ playbooks for onboarding, implementation, NPS, risk workflows, and sales-to-CS handoff. Then I used CRM automation to monitor health, trigger risk alerts, and raise first-contact resolution by 14 points.

Professional experience

Customer success leadership in healthcare SaaS.

My experience is centered on retention, onboarding, customer operations, and cross-functional partnership inside lean, high-accountability SaaS teams.

My career includes two Director-level CS roles at HIPAA compliance SaaS companies, bookended by independent consulting work applying that same expertise directly to healthcare organizations.

Independent HIPAA Compliance Consultant

New York, NY (Remote) • June 2025 to Present

Advise healthcare organizations on HIPAA compliance strategy, Security Risk Assessments, and gap analyses aligned with federal requirements.
Build and maintain a SaaS compliance platform with policy management, training delivery, incident tracking, and BAA auto-execution.
Design automated onboarding workflows and compliance monitoring systems for small-to-midsize healthcare providers.
Consult on technical safeguards, access controls, and breach response planning.

Director of Customer Success, AccountableHQ

Fort Worth, TX (Remote) • August 2022 to June 2025

Built and scaled the customer success function as a department of one, supporting 600+ healthcare organizations and $10M ARR while maintaining 98% retention.
Developed automated playbooks, onboarding flows, and CRM workflows that reduced onboarding time by 25 percent and saved 3.2 hours per week in manual effort.
Created CRM-driven automations using HubSpot, Zapier, and n8n to monitor customer health, trigger risk alerts, and increase first-contact resolution in Intercom by 14 percent, from 72 percent to 86 percent.
Contributed to $13K in quarterly upsells by identifying unreported expansion and adding satellite offices at scale.
Partnered with Product, Engineering, Marketing, and Sales to operationalize voice-of-customer insights, accelerate GDPR rollout, and prioritize roadmap decisions.

Independent HIPAA Compliance Consultant

New York, NY (Remote) • March 2020 to August 2022

Provided HIPAA compliance consulting to healthcare organizations including private practices, behavioral health providers, and multi-location groups.
Conducted Security Risk Assessments and gap analyses aligned with federal HIPAA requirements.
Developed tailored policies and procedures, employee training programs, and BAA management workflows.
Built compliance tracking automation to streamline documentation and reduce manual overhead.

Director of Customer Success, Compliancy Group

Greenlawn, NY • April 2015 to February 2020

Led high-volume HIPAA compliance implementations for approximately 1,000 healthcare practices over roughly three years, including 200+ entities within the Fort Drum Regional Health Planning Organization network and approximately 200 optometry practices using The Guard, the American Optometric Association’s endorsed HIPAA compliance software.
This work included implementations across nursing homes, hospitals, hospice and palliative care, primary care, behavioral health, EMS, first responders, optometry, and ophthalmology.
Managed the full customer lifecycle for 2,000+ healthcare clients while supporting HIPAA compliance through a proprietary SaaS platform.
Built and led a team of four, automating onboarding workflows and CSAT/NPS programs to scale enablement and performance tracking.
Designed onboarding programs and training curricula that drove a 95 percent CSAT average and reduced inbound support requests by 12 percent year over year.
Partnered with channel leadership to grow MSP upsell and cross-sell opportunities by 17 percent.
Created mutual success plans, persona-based guides, how-to video libraries, and train-the-trainer resources that improved adoption and gave customers clearer ownership of next steps.

Education and certification

Formal background and domain credential

Bachelor of Arts, Cinema Production, Binghamton University.
Certified HIPAA Professional (CHP), 2014.

Leadership approach

How I lead post-sales work.

I am most effective in environments that need better structure, better customer signal, and stronger execution without sacrificing trust or responsiveness.

What I build

I design the systems behind retention. That includes onboarding sequences, health frameworks, escalation paths, training assets, handoff playbooks, and feedback loops that keep Product close to reality.

I have done this across 600+ healthcare organizations and roughly 1,000 HIPAA implementations. In these environments, implementation quality and trust matter as much as expansion.

What hiring teams can expect

I combine operational rigor with calm judgment. I build automation and process, but I know when a situation needs direct communication and steady account leadership.

That includes 95% CSAT, a 25% onboarding reduction, a 14-point FCR lift, and 17% channel growth driven through better post-sales execution.

Recommendations

How colleagues describe my work.

The same strengths show up consistently: leverage, customer trust, and the ability to turn complexity into repeatable execution.

These come from colleagues in engineering, product, and leadership. We worked together in fast-moving SaaS teams where customer outcomes shaped company direction.

Omar Barazanji
Machine Learning / MLOps / Agentic AI Engineer

Charles is a master of automation, allowing him to operate with the output of a much larger team while working as a department of one.

Barry Devin Hecker
Director of Product Management

There is no customer service issue that he cannot solve. His empathy and patience know no bounds.

John Sherling
Chief Mechanical Engineer

Charles always goes above and beyond for his customers as well as his friends. He looks at solving customer success issues as a unique puzzle, requiring attention be provided to each circumstance in a way that customers rarely receive these days, but definitely appreciate and remember.

Platforms and tools

Core strengths and systems I use.

The first row reflects leadership strengths. The second shows the systems and platforms I have used to support visibility, automation, and better post-sales execution.

I pick tools that show me customer health in real time. Automating repetitive work frees me up for strategic conversations, at-risk accounts, and cross-team alignment.

Leadership strengths

Customer Success Leadership HIPAA Compliance Stakeholder Management B2B SaaS Voice of Customer Onboarding and Retention

Systems and platforms

HubSpot Intercom Mixpanel Zapier n8n Vitally

Open to Customer Success leadership conversations.

I am a strong fit for teams hiring a Director or Head of Customer Success who can improve onboarding, strengthen retention, and build post-sales structure that scales.

Email Charles Message on LinkedIn