AJ Weinsieder

AJ Weinsieder

Executive Customer Success & Implementation Leader

I build Customer Success, Implementation, and Customer Operations organizations from the ground up, then operationalize them to improve retention, accelerate delivery, and scale performance.

Built Customer Success and Implementation organizations from scratch. Scaled Customer Success to eight direct reports. Reduced churn 18%. Shortened implementations from 10+ weeks to approximately 6 weeks. Led enterprise technology deployments across more than 900 locations.

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Proven Impact

18%

Reduced enterprise churn year-over-year through structured account health programs

25%

Increased add-on adoption across high-value accounts through targeted engagement

40%

Reduced resolution time and cut ticket backlog within 90 days of building CS infrastructure

4x faster

Improved first-response time from 24+ hours to under 2 hours after standing up support operations

40% shorter

Cut onboarding timelines from 10+ weeks to approximately 6 weeks through process redesign

900+

Hotel properties migrated to new systems at Wyndham with 100% adoption and zero critical failures

About Me

I'm a SaaS operator with 20+ years of experience across customer success, implementation, and program management. My background spans enterprise SaaS, federal programs, hospitality technology, and digital platforms.

At every stage of my career, I've been the person who builds what doesn't exist yet: the first implementation process, the first CS playbook, the first training program. I hire the team, develop the people, and make sure it runs after I step back.

I've managed multi-million-dollar renewal portfolios, led 900+ location system migrations, directed federally regulated credentialing operations with 100% compliance, and built an 18-year profitable online platform from zero.

Core Capabilities

Customer Success Leadership
Implementation Program Design
Team Building & People Management
Enablement & Training Development
Onboarding Process Optimization
Enterprise Account Management
Cross-Functional Collaboration
Operational Infrastructure Design

Career Highlights

Customer Success Team Leader

Promptly Inc  |  2023–2025

Built and led the enterprise CS org from 2 to 8 direct reports. Owned hiring, performance management, and team development. Managed a multi-million-dollar recurring revenue portfolio, reduced churn 18% YoY, and improved add-on adoption by 25%.

Implementation Team Leader

Promptly Inc  |  2021–2023

Designed and built the Implementation department from scratch: created the onboarding methodology, hired and trained the team, developed my direct successor, and cut delivery timelines from 10+ weeks to approximately 6 weeks. Trained 10+ partner team members on implementation processes.

Systems Trainer & Technical Integration Lead

Wyndham Hotels  |  2018–2020

Led system migrations and technical enablement across 900+ hotel properties. Achieved 100% adoption with zero critical failures by designing structured training programs and hands-on delivery at scale.

Supervisory Trusted Agent

Department of Homeland Security  |  2008–2012

Directed federally regulated credentialing operations processing more than 5,000 secure credentials annually while maintaining 100% DHS/FBI compliance. Established operational controls that reduced processing time 38% while decreasing rejection rates 30%.

Founder & CEO

AquariumPros  |  1999–2020

Founded, built, and operated a profitable digital subscription platform serving more than 20,000 members over two decades with greater than 95% member retention. Held full P&L responsibility while leading operations, technology, marketing, customer support, vendor management, and long-term business growth.

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Open to senior roles in Customer Success, Implementation, Program Management, and Enablement.

Remote preferred  |  Open to relocation within 12 months  |  Sarasota, FL