Charles Weiselberg
I build the automations, playbooks, and onboarding systems that let small CS teams punch way above their weight. HIPAA compliance expert, CRM automation nerd, and the person who turns customer feedback into shipped features.
About
Professional Experience
Director of Customer Success — AccountableHQ
Fort Worth, TX (Remote) • Aug 2022 - Jun 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% (12 to 9 weeks) and saved 3.2 hours/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% (72% to 86%).
- Contributed to $13K in quarterly upsells by identifying unreported expansion and adding satellite offices at scale.
- Authored and launched 35+ playbooks covering onboarding, implementation, account stages, NPS, risk workflows, and sales-to-CS handoff, reducing time to value and supporting consistent execution across all accounts.
- Partnered cross-functionally with Product, Engineering, Marketing, and Sales to operationalize VoC insights, accelerating GDPR rollout by 4 to 6 weeks and prioritizing roadmap features.
- Migrated CRM systems (Vitally to Custify to HubSpot), led implementation three months ahead of schedule, and optimized playbooks for in-app guidance, boosting product usage and reducing support load.
Director of Customer Success — Compliancy Group
Greenlawn, NY • April 2015 - Feb 2020
- Managed end-to-end customer lifecycle for 2,000+ healthcare clients, achieving 98% retention while supporting HIPAA compliance via a proprietary SaaS platform.
- Built and led a team of 4, automating onboarding workflows and CSAT/NPS programs in InfusionSoft to scale customer enablement and performance tracking.
- Designed onboarding programs and training curricula to accelerate time to value, achieving a 95% CSAT average and cutting inbound support requests by 12% YoY.
- Partnered with a new Channel Manager to increase upsell/cross-sell MSP opportunities by 17%.
- Created mutual success plans, outlining outcomes, milestones, and risk indicators to drive accountability and adoption.
- Led change management and enablement initiatives: authored persona-based guides, launched how-to video libraries, and created train-the-trainer materials for scaled accounts.
- Analyzed usage data and health indicators to flag risks and surface opportunities, enabling proactive outreach and champion cultivation.
- Facilitated success planning, onboarding calls, compliance walkthroughs, and renewal prep for 8 to 12 enterprise clients daily, tailoring enablement by role and compliance stage.
Education & Certifications
Bachelor of Arts
Binghamton University
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
14%
Increase in first-contact resolution in Intercom (72% to 86%) through CRM-driven automations
35+
Playbooks authored covering onboarding, NPS, risk workflows, and sales-to-CS handoff
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