Charles Weiselberg
Two startups, one builder - $10M ARR and 98% retention.
I've worked nearly a decade in healthcare SaaS Customer Success.
In six years as a department of one, I automated CRM workflows until my one-person operation delivered like a team of ten -
then I built and led the actual team when the time came.
Besides that, I've successfully spent 8+ years improving onboarding speed, reducing churn, and enhancing the customer experience.
About
Professional Experience
Director of Customer Success — AccountableHQ
Fort Worth, TX (Remote) • Aug 2022 - Jun 2025
- Single-handedly built and scaled the customer success function, growing from 180 to 600+ healthcare orgs while supporting $10M ARR and maintaining a 98% retention rate without adding headcount.
- Reduced onboarding time to achieve HIPAA compliance when using Accountable by 25% (from 12 weeks down to 9 weeks).
- Led 1:1 onboarding meetings for SMB healthcare clients, aligning their Accountable implementation and product usage goals with HIPAA requirements and industry best practices.
- Built CRM automations to track stages of the customer journey, monitor customer health score, catch churn risks early, and trigger proactive outreach across 600+ accounts.
- Served as VoC (Voice of the Customer) across Product, Engineering, Marketing, and Sales, turning feedback and behavioral data into roadmap and GTM (Go-to-Market) priorities.
- Maintained a perfect compliance record across 600+ clients with zero audit failures, zero fines, and zero corrective action plans.
Director of Customer Success — Compliancy Group
Greenlawn, NY • April 2015 - Feb 2020
- Managed the full customer lifecycle for healthcare clients navigating HIPAA compliance using Compliancy Group’s SaaS platform, The Guard.
- Automated workflows and playbooks in InfusionSoft CRM, scaling team capacity across thousands of users.
- Built and led a team of four to consistently exceed retention and NPS (Net Promoter Score) targets.
- Cut inbound support requests 12% YoY by building self-service resources and training materials.
- Designed scalable onboarding programs based on data-driven concepts that streamlined client time-to-value.
- Grew partner cross-sell/up-sell opportunities 17% by developing targeted training programs.
Education & Certifications
Bachelor of Arts, Cinema Production
SUNY Binghamton
Certified HIPAA Professional (CHP) • 2014
Focus
Process Optimization
Automating workflows and eliminating inefficiencies to maximize productivity and reduce operational costs.
- Building CRM automations that track customer journey stages and trigger proactive outreach
- Designing workflows that let one person deliver results like a team of ten
- Auditing business practices bi-annually to gauge effectiveness and ensure an A++ customer experience
- Backtesting new workflows against previous benchmarks prior to launch
- Reducing onboarding timelines through systematic process improvement
HIPAA Compliance
Guiding healthcare organizations through complex regulatory requirements with zero audit failures.
- Building bulletproof compliance plans that protect organizations and their patients
- Translating technical requirements into actionable steps for non-technical teams
- Bringing customers to their 'A-ha' moment when difficult concepts click
- Creating self-service resources that reduce support burden while maintaining compliance
- Maintaining perfect track record: zero fines, zero corrective action plans
Voice of Customer
Turning customer conversations into product improvements and company-wide priorities.
- Bridging communication between customers and Product, Engineering, and Sales teams
- Using behavioral data from Mixpanel and Amplitude to identify adoption blockers
- Building feedback loops that drive retention and reduce churn risk early
- Empathetic interactions that feel personal, not procedural
Impact
98%
Client retention rate maintained across 600+ healthcare organizations over nearly a decade
$10M
Annual recurring revenue supported as a solo CS operator before scaling the team
600+
Healthcare organizations guided to full HIPAA compliance through structured onboarding
25%
Reduction in onboarding time, cutting timelines from 12 weeks down to 9 weeks
30%
Boost in efficiency from CRM optimization, segmentation, and automated persona assignment
15+ hrs
Recovered weekly by automating repetitive tasks and assigning playbooks programmatically
12%
Year-over-year reduction in support requests through self-service resources and training
0
Clients ever fined, audited, or issued corrective action plans by regulatory bodies
Recommendations
Omar Barazanji
Machine Learning / MLOps / Agentic AI Engineer
"Charles helped Omni Aura build our CRM and CS workflows from the ground up. He is a master of automation, allowing him to operate with the output of a much larger team while working as a department of one. Beyond his technical skills in CS Ops, he brings a refreshing level of emotional intelligence to the role. He understands that great workflows only work if they serve the human on the other end. Highly recommend working with him."
Barry Devin Hecker
Director of Product Management
"Working with Charles is a pleasure. He goes above and beyond for his coworkers and clients. There is no customer service issue that he cannot solve, as his empathy and patience know no bounds. Charles is extremely tech-savvy and there isn't a piece of software he can't learn or teach. I'd recommend having him in your organization if you're looking to add a pleasant, hard-working team member by your side."
Katherine Muserilli
Associate Attorney
"I have known Charles for 15+ years now and in that time he has become quite the tech and healthcare SaaS compliance expert. It was a field he taught himself but never missed a step. For some reason this obscure law just clicked for him. What is something I have found more impressive than that, is his ability to break down the dense language of the law into bite-size pieces which bring anxious users off-the-edge, oftentimes these nervous customer become his biggest champions and most successful of all his customers."
John Sherling
Chief Mechanical Engineer
"I've been a close friend of Charles (Chuck) Weiselberg for many years. We first met in college, where we bonded over our mutual love of music. As time went on, we both found our professional tracks, but one thing I must say about Charles is he 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 when someone gives it their all like Charles."
Allison Cole
Associate Accountant at ESFM USA
"Charles has been a dear friend of mine for 15+ years and in that time it has been a pleasure watching him grow personally and professionally. He was always professional and courteous in nature but in the CS roles he's filled of late, I've seen him grow into a true professional and not merely a 'rep'. He balances his compassionate nature with cutting-edge tech knowhow to give his clients the best possible onboard and lifecycle experiences."
Skills
Interests
Lifelong musician and sound design enthusiast, lover of cinema and visual storytelling, amateur web designer, and SEO specialist. Always learning, always building.
Contact
If you're hiring for Customer Success leadership or want help tightening onboarding, retention, or internal processes, I'm happy to talk. Let's connect and see how I can help your team succeed.
What drives me: data privacy in a high-tech world. Before this career, I thought HIPAA was just red tape. Eight years changed that. Without HIPAA, Protected Health Information would be scattered across the internet with no guardrails. I do this work because compliance done right protects real people. This expertise translates directly to AI governance and responsible AI deployment—building trust between emerging technology and the people it serves.
Email: cweiselberg1@gmail.com • LinkedIn: Message me here