AJ Weinsieder
Customer Success, Implementation & Enablement Leader
I build things from scratch: teams, departments, processes. Then I make sure they run.
At Promptly, I built the Implementation department from the ground up, then moved over to build the Customer Success org, scaling from 2 direct reports to 8 while managing an enterprise account portfolio. Before that, I led system migrations across 900+ hotel properties at Wyndham and directed federally regulated operations with 100% compliance at DHS.
I'm currently open to senior roles in Customer Success, Implementation, Program Management, and Enablement.
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 5,000+ credentials annually with 100% compliance. Reduced processing time 38% through workflow redesign.
Founder & CEO
Built and operated a profitable online platform for 18 years, growing to 20,000+ members with over 95% retention. Managed all technical infrastructure, community operations, and business development.
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