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.
Let's ConnectProven 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
Career Highlights
Customer Success Team Leader
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
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
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
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
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.
Let's Connect
Open to senior roles in Customer Success, Implementation, Program Management, and Enablement.
Remote preferred | Open to relocation within 12 months | Sarasota, FL