Looking for a job

AJ Weinsieder

@ajweinsieder1

Customer Success and operations leader who builds teams, fixes broken processes, and turns complex customer programs into scalable operations.

United States

Message

What I'm looking for

I’m looking for a fully remote role where I can lead or improve Customer Success, Implementation, Customer Operations, Enablement, or related programs. I’m strongest in roles that combine people leadership, process improvement, cross-functional execution, and solving complex customer or operational problems.

I’ve spent more than 20 years leading customer operations, implementation, and service teams, with much of my recent work focused on SaaS and technology.

At Promptly, I joined when the company was still very small and built the Implementation function from the ground up. As the company grew, I moved on to build Customer Success, eventually leading an eight-person customer-facing team. Along the way, I created the processes, playbooks, training, escalation paths, and operating routines needed to support that growth.

My work has included reducing implementation timelines from more than 10 weeks to about six, reducing churn 18%, cutting resolution time 40%, and maintaining roughly 95% CSAT. Earlier in my career, I led a technology migration across more than 900 hotel properties and managed a 350-person workforce in federally regulated operations.

I’m most interested in remote leadership roles where I can build or improve Customer Success, Implementation, Customer Operations, Enablement, or related functions. I do my best work when there is something complicated that needs to be made simpler, more organized, and easier for both customers and teams to navigate.

Experience

Work history, roles, and key accomplishments

Current

Independent AI Systems Consultant

Current

Independent

Dec 2025 - Present (8 months)

Partnered with local businesses to design AI automation and advise on SaaS vendor selection. Built AI-driven intake and report generation for an environmental assessment company, cutting report-consolidation time by ~30%. Currently developing a multi-stage AI automation platform for email/ATS intake and screening.

AI Automation SaaS Vendor Selection Claude ChatGpt Google Workspace Process Optimization

Customer Success Team Manager

Promptly Inc

Jun 2023 - Dec 2025 (2 years 6 months)

Built and led an 8-person Customer Success function, improving handoffs, escalation discipline, and lifecycle accountability. Introduced SLA and operating controls that cut resolution time 40% and backlog 30% within 90 days, reduced churn 18% YoY, and increased add-on adoption 25%.

Customer Success Team Leadership SLA Management Escalation Management Customer Health Monitoring Process Improvement Data Analysis Stakeholder Management

Implementation Team Manager

Promptly Inc

Jun 2021 - Jun 2023 (2 years)

Built the Implementation department from zero, owning delivery governance, SOPs, hiring, training, partner enablement, and development of a direct successor. Owned complex healthcare SaaS implementations from sales handoff through configuration, testing, training, UAT, go-live, stabilization, and transition to Customer Success.

Implementation Management Healthcare SaaS Electronic Health Records (EHR)Configuration Testing Training UAT Go Live Customer Success Process Improvement SOPs Hiring Partner Enablement Data Integrity Regulatory Compliance Cross Functional Collaboration Product Validation

Systems Trainer & Tech Team Lead

ENG Infotech / Wyndham

Oct 2018 - Apr 2020 (1 year 6 months)

● Directed a complex PMS migration across 900+ hotel properties, coordinating corporate, vendor, technical, and property stakeholders to achieve 100% adoption with zero critical failures.

Founder & CEO

AquariumPros

Jan 1999 - Jan 2020 (21 years)

● Built and operated a profitable digital subscription platform serving 20,000+ members; owned P&L, platform operations, customer retention, and growth while sustaining >95% retention.

Property Manager

Brookfield Condominium Services

Oct 2015 - Sep 2017 (1 year 11 months)

• Managed 405-unit complex with $3.5M budget; ensured 100% regulatory compliance
• Improved Board satisfaction 72% to 91%; coordinated multi-million dollar capital projects on-time and on-budget
• Managed 15+ vendors; implemented preventative maintenance reducing emergency repairs >20%

Property Manager (Condominium)

Malvern Condominium Property Management

Sep 2014 - Aug 2015 (11 months)

• Managed three corporations (250+ units, $3M+ budgets); maintained 100% compliance with zero violations
• Improved resident satisfaction 60% through responsive service and proactive communication

Supervisory Trusted Agent

US Department of Homeland Security

Jun 2007 - Nov 2012 (5 years 5 months)

• Directed Honolulu Enrollment Center processing 5,000+ TWIC applications annually; maintained 100% federal compliance
• Supervised 5 agents; reduced processing time from 45 to 28 minutes; decreased rejections 30%; zero security breaches

Director of Operations

Private Security Inc

Jun 2007 - Nov 2012 (5 years 5 months)

• Directed operations for 50 full-time and 300 part-time personnel; reduced payroll errors 60%; maintained 95% retention
• Improved client satisfaction 78% to 94%; increased retention 22%; reduced overtime costs 18% and supply costs 30%