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 customer churn 18% through scalable Customer Success operations.
25%
Increased add-on adoption 25% through structured customer education and lifecycle management.
40%
Reduced resolution time 40% and support backlog 30% within 90 days of building the Customer Success organization.
4x faster
Improved first-response times from more than 24 hours to under 2 hours through operational redesign and SLA management.
40% shorter
Reduced implementation timelines from 10+ weeks to approximately 6 weeks through standardized delivery frameworks.
900+
Led enterprise deployment across 900+ hotel properties 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.
Organizations hire me to build what doesn't exist yet, then scale it. Throughout my career, I've established Customer Success, Implementation, and operational organizations, developed the people leading them, and created repeatable systems that improve customer outcomes and business performance.
Core Capabilities
Career Highlights
Customer Success Team Leader
Built the Customer Success organization from the ground up, scaling the team to eight direct reports while leading hiring, coaching, performance management, and operational leadership. Established scalable customer success frameworks that reduced churn 18%, improved first-response times from more than 24 hours to under 2 hours, reduced support backlog 30%, and increased add-on adoption 25%.
Implementation Team Leader
Built the Implementation organization from the ground up, establishing delivery methodology, operational processes, hiring, onboarding, and team development before successfully transitioning leadership to a trained successor. Directed enterprise SaaS implementations from sales handoff through configuration, training, UAT, go-live, and early customer success while reducing implementation timelines from more than 10 weeks to approximately 6 weeks.
Systems Trainer & Technical Integration Lead
Directed enterprise deployment of a property management platform across more than 900 hotel properties, coordinating implementation, training, and technical integration with zero critical deployment failures. Developed standardized training programs that achieved 100% user adoption while partnering with technical and operational stakeholders to ensure successful enterprise rollouts.
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 Executive and Senior Leadership opportunities in Customer Success, Implementation, Customer Operations, and Professional Services.
Remote preferred | Open to relocation within 12 months | Sarasota, FL