Charles Weiselberg | 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.

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.

At-risk account recovery

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

When I joined AccountableHQ, I was notified that our largest client, a major mental health franchise, was not progressing through our HIPAA compliance process as smoothly as previously assumed. After digging into the data to see what was going sideways across so many franchise locations, I introduced myself directly to each clinic and invited them to join me for live onboarding sessions. From there, product usage increased, meetings booked with me increased, and stagnation declined.

Personally contacted franchise locations to establish trust and reset the relationship.
Combined 1:1 onboarding with automated follow-up so momentum did not die between calls.
Implemented around 150 franchise locations and reduced onboarding time from 12 weeks to 9 weeks.

Voice of customer

Turned customer feedback into product movement.

I made customer feedback a standing topic in weekly product syncs, documented recurring friction clearly, and pushed for prioritization that reflected what customers were actually hitting so Product, Sales, and Customer Success could operate from the same customer reality.

Operational leverage

Used systems to keep service personal.

I rely on automation to preserve human attention for the moments that matter most: implementation friction, at-risk behavior, escalations, and expansion opportunities, while still managing 600+ organizations and $10M ARR with lean resources.

Scale without headcount

Built the CS machine before building the team.

I authored 35+ playbooks covering onboarding, implementation, NPS, risk workflows, and sales-to-CS handoff, then 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.

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.

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: onboarding sequences, customer health frameworks, escalation paths, training assets, handoff playbooks, and feedback loops that keep Product close to reality.

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

What hiring teams can expect

I combine operational rigor with calm customer judgment. I can build automation and process, but I also know when a situation requires direct communication, clarity, 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.

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.

Omar Barazanji
Machine Learning / MLOps / Agentic AI Engineer

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

Barry Devin Hecker
Director of Product Management

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.

John Sherling
Chief Mechanical Engineer

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.

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