Customer success leader. AI builder.

A decade deploying AI and HR technology at IBM, Moody's, Gloat, and ThisWay Global. Now I build AI products.

Thomas Sikler
Location
St. Augustine, FL
Career
22-year career
Employers
IBM, Moody's, Gloat, Giant Eagle

Across the customer lifecycle

Results from every stage of the work, from first onboarding through renewal, expansion, and the team that delivers it.

  1. Onboard and implement

    65%

    faster time-to-readiness from a rebuilt onboarding experience

    ThisWay Global
    21 days

    cut from time-to-fill after re-implementing talent acquisition systems

    Moody's
  2. Drive adoption

    +18%

    feature adoption from executive product-optimization reviews

    IBM
    100%

    review-cycle completion, up from 65%, after re-implementing performance management

    Moody's
  3. Retain

    100%

    gross retention against a 95% target, with zero churn

    Gloat
    94%

    gross retention with an NPS of 73 against a goal of 65

    IBM
  4. Expand

    ~121%

    net retention, with ARR up 21%

    Gloat
    +22%

    above target on a 55-client portfolio, grown 9% year over year

    IBM
  5. Scale the team

    39 days

    faster new-hire time-to-proficiency, with turnover cut 50%

    Gloat
    +15 pts

    customer satisfaction from a new CS and services operating model

    IBM

Experience

  1. Black Cloud

    December 2022 to Present

    Founder & Principal · AI Product Builder & Consultant

    Independent product studio and applied-AI consulting practice spanning AI engineering, product design, and creative work.

    See the builds
  2. ThisWay Global

    April 2024 to February 2026

    Manager, Customer Success & Experience

    • Led all customer experience (success, support, implementation, onboarding, adoption, and renewals) across the lifecycle; built an enhanced onboarding experience that reduced time-to-readiness by 65%.
  3. Gloat

    January 2022 to November 2022

    Manager, Enterprise Customer Success

    • Owned renewals and expansion for 12 Enterprise and Mid-Market clients. Delivered 100% gross retention (vs. 95% target, zero churn) and ~121% net retention, growing ARR 21%, the highest upsell on the CS team.
    • Built new CS operational standards and served as CSM trainer, cutting new-hire time-to-proficiency by 39 days and turnover by 50%.
  4. Moody's

    September 2019 to August 2021

    Associate Vice President, HR Technology & Service Delivery

    • Led re-implementation of Talent Acquisition systems (ATS, candidate CRM, careers site), cutting time-to-fill by 21 days, raising hiring-manager satisfaction 40%, and cutting recruitment agency spend by seven figures.
    • Re-implemented Performance, Goal-Setting & Succession, driving 100% review-cycle completion (up from 65%) and facilitating the company's first executive succession cycle.
  5. IBM

    June 2014 to June 2019

    Global Leader, Customer Success, Solution Design & Consulting

    • Designed and launched new Consulting and Professional Services offerings, building and training the team and all operations, with six-figure new revenue and upsell through a paired Solution Design pre-sales function.
    • Ran Product Optimization Executive Reviews that lifted feature adoption 18% and drove six-figure services revenue; designed the digital CS model for SMB (+10 NPS).

    Regional Leader, Customer Success

    • Grew a 55-client Enterprise and Mid-Market portfolio 9% YoY, finishing 22% above target.
    • Led a new CS and Professional Services operating model, cutting operating costs by seven figures, raising satisfaction 15 points, and holding 94% gross retention with an NPS of 73 (goal 65).
  6. Giant Eagle

    November 2004 to March 2014

    Leader, People Systems → Talent Acquisition → HR

    • Implemented SAP SuccessFactors HCM and LMS (100% company-wide OSHA training compliance, a company first) and pre-employment assessments (six-figure annual savings, +32% quality of hire).
    • Stood up the organization's first applicant tracking system and trained 75 HR professionals, for a seven-figure total cost reduction.
    • Promoted to Regional HR Leader; rolled out behavior-based interviewing to 120 leaders (+18% quality of hire) and led UFCW collective-bargaining negotiations.

Builds

Products I designed, built, and shipped through Black Cloud, my product studio.

arrangementLab home page: Finish what you start, with launch pricing and a free trial

arrangementLab

Live

A visual song-arrangement planner for music producers: map a whole song on a canvas, analyze a loop in the browser, and follow production tips section by section.

Built it deliberately without AI, because a simpler deterministic approach was the better engineering call. Real-time audio analysis runs in the browser, so audio never leaves the user's machine.

  • React
  • Vite
  • Web Audio API
  • Tailwind CSS
arrangementlab.com
DriveMosaic home page: See what's eating your disk, with a download button for Mac

DriveMosaic

Live

A native macOS disk analyzer that shows where your storage went as an interactive treemap.

Shipped a signed, notarized native app with a free scanner and a one-time Pro unlock.

  • Swift 6
  • SwiftUI
  • CryptoKit
  • macOS
drivemosaic.app

Bindery

Working demo

A reference assistant for independent insurance agencies. It answers coverage questions from the agency's own documents, cites every answer, declines when it isn't sure, and hands claims and advice to a licensed agent.

Designed and built the whole system: hybrid retrieval that blends vector and keyword search, streaming cited answers, per-agency document storage, and a golden-set evaluation harness judged by Claude.

0.72 → 0.86

retrieval recall

0.79 → 0.87

answer correctness

Scores on a 17-question test set judged by Claude, before and after a retrieval fix. The harness caught the bug before launch.

  • Python
  • FastAPI
  • Supabase pgvector
  • Anthropic API
  • React
  • Vite
exitPlan home page: a floor plan with an escape route and an 82 out of 100 readiness score

exitPlan

Live

An AI home emergency planner. A homeowner walks each room with a phone and gets a floor map, escape routes, a prioritized task list, and a readiness score.

Built and shipped it end to end: frames are pulled from video inside the browser, analyzed by Claude's vision model, and discarded. The video never leaves the phone, and the plan lives on the user's device.

  • Next.js
  • TypeScript
  • Anthropic API (vision)
  • Vercel
exitplan.today

Customer success work samples

How I run account recovery, executive reviews, renewals, and adoption, in my own templates.

See the work samples

Skills and tools

Customer success

  • Enterprise Customer Success
  • Customer Experience
  • Implementation & Delivery
  • Technical Account Management
  • Renewals & Expansion
  • C-Suite Communication
  • Operational Strategy
  • Pre-sales & Solutions Engineering
  • Proof-of-Concept & Pilots
  • AI Deployment & Solution Design
  • Applied AI / LLM Integration
  • Product Development
  • Enterprise SaaS

Enterprise and HR tech

  • Gainsight
  • Salesforce
  • HubSpot
  • Zendesk
  • JIRA
  • SuccessFactors
  • Avature
  • Cornerstone
  • PeopleSoft
  • IBM Watson Talent

AI and machine learning

  • Claude
  • Anthropic API
  • Claude Code
  • Cursor
  • RAG (pgvector, hybrid retrieval)
  • LLM evaluation
  • Prompt engineering

Build and infrastructure

  • Python
  • TypeScript
  • React
  • Swift / SwiftUI
  • FastAPI
  • REST APIs
  • Vite
  • Web Audio API
  • Supabase
  • Vercel
  • AWS
  • Azure
  • CryptoKit

Certifications and programs

  • Apple Developer Program
  • Google Play Developer
  • IBM Agile Practitioner
  • SAP SuccessFactors HCM
  • IBM Design Thinking
  • Prosci Change Management
  • IBM Watson Talent Workbench
  • Korn Ferry Competency Modeling
  • Korn Ferry Competency-based Interviewing

Awards

  • 2014 IBM Customer Success Achievement
  • 2012 Giant Eagle Community Service
  • 2007 Giant Eagle Team Achievement

Education

  • Studied Electronic Media Production, Kent State University

Let's talk.

Email is the fastest way to reach me.

t.sikler@gmail.com

Outside work: guitarist and producer, performing live since 1996.