Many of those companies were startups where layoffs were part of the rhythm. I used the gaps between roles to keep studying on the tech side: Salesforce certifications, business analyst training, and for the last three years, deep dives into AI. Now I’m focusing on learning skills that take what I did in brick-and-mortar full circle, but do that online in a remote role. You can read about each stretch below.
Career History
2023 – Present Independent Studies
Three years of self-directed study. Two parallel tracks: the Salesforce Business Analyst path and deep AI study with a portfolio of builds.
- Salesforce Certified Associate.
- Salesforce Trailhead Business Analyst path, Ranger rank (75,750 points, 82 badges).
- Creating User Stories as a Business Analyst.
- Business Process Mapping as a Business Analyst, including current state and future state stakeholder interviewing.
- Scrum and Agile methodologies.
- CRM training on Salesforce and GoHighLevel: client engagement, follow-up processes, reporting, dashboards, workflow optimization.
- Clicked: real-world Business Analyst experiences in Slack, where I became the go-to person for how to use AI to complete common BA tasks.
- Autonomee: AI-builder community (Sjoerd Tiemensma, Goda Go).
- Mark Kashef Claude Code Magic Course (19 lessons).
- Anthropic Essentials: official Claude Code training.
- Daniel Riley AI Video Boot Camp.
- Julian Goldie AI SEO.
- Life at a Glance: custom dashboard integrating daily ease, tasks, notes, and projects.
- Entertainment Hub: tracker for movies, series, and Audible audiobooks. Pulls IMDB and platform info from the web, plays trailers, and keeps a want-to-watch queue, a currently-watching list, and a scored history in one place.
- AI recipe app: cooking assistant that works from what’s actually in your kitchen. Photo or voice inventory of freezer, fridge, and cupboards with expiration dates. Saves recipes with notes and dietary scoring. Ask it “what should I make?” and it pulls from items expiring soon and your highest-rated recipes. Includes a cook feature.
- Visual Prompt Builder: web app on Netlify with a Gemini 2.5 Flash backend that structures prompts for AI image and video work. Built during Daniel Riley’s AI Video Boot Camp.
- Friends Job Search Dashboard: job-search platform built for former colleagues after the Ontrak layoff. Uses Apify to scrape leads by criteria, tailors the resume per posting with ATS-aware optimization, and generates a cover letter from a template.
- Ontrak Call Guide portfolio rebuild: the 2020 scripting tool, rebuilt as an AI-enhanced portfolio piece.
Tools Claude Code, Claude Cowork, Claude API, ChatGPT, Gemini, Convex, Supabase, n8n, Retool, Bubble, Notion, Apify, Telegram Bot API, GoHighLevel, Salesforce, Elements Cloud, Lucidchart, Figma, Canva, DaVinci Resolve, Loom…
Nov 2019 – Nov 2021 2024 – Aug 2025 Ontrak, Inc.
Ontrak phone work with health plan members on behavioral-health programs. Treatment-resistant, care-avoidant populations.
Struggling agents were assigned to shadow me. After working with several of them, I saw they were all hitting the same wall. Remote work meant there was no day-to-day pulse the way there was in a brick-and-mortar operation. This was before COVID, when work from home was still new, and nothing was in place yet to give remote teams that kind of visibility.
I had already been working from home as a supervisor. In the brick-and-mortar, this was exactly the work I had done as a manager and trained consultants to do. I put together a web page that held everything we did on a call in one place, easy to follow. I brought it to the department heads. They loved it. Adoption was voluntary but near-universal.
After Ontrak lost two major clients in 2021, successive layoffs cut the department from 140 reps down to 7. I was let go in the final round.
Brought back in 2024 when Ontrak was rebuilding the department in anticipation of new business.
The company went out of business permanently in August 2025.
Oct 2022 – Jul 2023 K Health
Founding team member of the Member Activation department. Responsible for outreach to tens of thousands of patients to qualify them, convert them, and assist with onboarding.
The leads came in through Google Sheets, but patient records lived in Salesforce. We had to go back and forth between the Google Sheet and Salesforce, and then back to the sheet again to make notes. It was very clunky. I taught myself Notion in a week and built the team’s call-management system inside it: today’s calls, rolling history by date with outcomes, pending follow-ups, per-person notes, lead-scoring tiers (A through D, ranked by likelihood to close), and conversion counts by tier.
The system became the department’s source of truth for conversion reporting.
Salesforce is a very popular platform, and I wanted to understand it better. I wanted to understand it well enough to have more control over the changes that would improve workflow. I also wanted to understand how a 10-minute fix could sit in the backlog as long as a 10-hour or a 10-day fix. That led me to Agile and Scrum methodologies.
The department was one of 11 closed in July 2023 when K Health’s go-to-market strategy changed significantly.
Full letter of recommendation available on request.
Sep 2016 – Jul 2019 Alliance Advisors
The company was standing up a remote outreach department and had no internal model for how the supervisor role should look. I brought what had worked in brick-and-mortar and adapted it for remote.
- On-the-phones onboarding. After their initial training, new agents were assigned to me and onboarded on live calls with me for their first week.
- Group chat for team questions. Before this, questions went directly to the supervisor in DMs. Same questions, multiple agents, all day. I moved them into a group chat where every answer became a training moment visible to the whole team. In that same channel, I posted hourly stats on talk time, conversions, and more. It turned into friendly competition. Agents would DM me things like “I’m going to beat John today.”
- Task system for agent requests. Before this, agents DM’d the supervisor whenever they needed something: research the supervisor needed to run, a call note that needed correcting, a policy clarification. The supervisor had to track it, and the agent sat waiting, sometimes behind two or three other agents already waiting on the same supervisor. I set up a system inside our messaging system (Chatwork) where agents created tasks for me instead. I worked through the tasks between coaching sessions and call-listening QA. When I ticked one off, the agent got a notification that it was done. Agents stayed on the phones.
As a result of these systems, my team had the highest talk time in the company.
Mar 2014 – Jun 2017 Institute of Reading Development
Inbound sales role selling summer reading programs to parents. My first pure phone-sales role: no face-to-face body language to read, just voice. I had to learn to listen without visual cues.
I came out of training and did not hear from anybody for about six weeks. When management finally reached out, it was to ask if I wanted to stay on for the college-classes season too. They told me what I had done straight out of training was “unprecedented.” Nobody had checked in because it was the height of the season and everybody was slammed. Their read on my performance: “if it’s not broke, don’t fix it.”
Overlapped with Alliance Advisors for my last ten months (September 2016 through June 2017). I did not return for the next IRD season because of the workload at Alliance Advisors.
Nov 2007 – Jun 2013 Jenny Craig
Hired back to Jenny Craig in 2007 for a $50M company-wide CRM rollout. The rollout kept getting pushed back for about two years, so while I waited I ran a center in the SF Bay Area.
- Center Director, SF Bay Area. Owned all aspects of running the center: hiring and staffing decisions, budget, inventory, training, scheduling, and the client experience. Double-digit year-over-year growth at my center while comparable locations were down as much as 30%. My center made 100+ previous-client calls daily; other locations did that volume weekly. I tossed out the sales script and had consultants make real care calls instead. They liked reaching out without a script, and clients loved hearing from them without being pressured to come back. Jenny Craig stayed top of mind when those clients thought about weight loss again.
- Consultant management and coaching. Owned the KPIs and metrics for every consultant on my team. Set individual goals and ran weekly one-on-ones to track progress against them. When someone was off pace, I coached them on the specific areas they needed to strengthen to hit their goal. Also responsible for PIPs.
- Market-level turnaround. A new role was created for me. I deployed location-to-location to streamline, declutter, and get struggling centers back on track.
- National CRM training tour. Across the U.S. and Canada. I developed the “Learn it, See it, Do it, Teach it” method for getting new centers fluent on the CRM fast. Read more about this approach →
- Back in the SF Bay Area market. Because of my fluency in the CRM, I was able to run two locations at once. I was also doing additional training for the West Coast market directors so they could better manage their own markets.
Laid off in June 2013 when Jenny Craig closed more than 100 locations.
Read the case study: Location Managers Were in Tears →Early Career
Before Jenny Craig: five years teaching web design at a private school in Maine, where training and building curriculum was the daily work. An earlier role at Jenny Craig in the 1990s as a Center Director. Management and training have been the throughline from the beginning.
Live Demos
Five-stage call guide with coaching notes
Interactive call structure built for Ontrak agents. Hover any stage to reveal coaching notes. Near-universal adoption was voluntary.
Open the live tool →AI job leads with fit scores and one-click tailoring
Jane Doe's sandbox: JJ scrapes leads, scores each one for fit, and generates a tailored resume and cover letter on demand.
Open the 4-minute audio tour → Or walk through the 18-page onboarding tour →Handwritten recipe cards turned into a searchable kitchen tool
215+ family recipes, freezer tracking, AI-assisted bulk add. Demo mode loads automatically with sample data.
Open the live demo → Entertainment HubOne place for everything you are watching, reading, and listening to
Search across streaming platforms, track progress, surface trailers and ratings. Demo mode opens with sample lists.
Open the live demo →Technology
Technology is my jam. It has always been easy for me to learn any new platform, and AI has made that easier still. If I get stuck, I screenshot it, ask AI, and work through it step by step.
- AI tools I use daily Claude (Code, Cowork, API), ChatGPT, Gemini, NotebookLM, MCP servers.
- AI image and video Nano Banana Pro, Midjourney, Higgsfield, Kling, Veo 3.1, DALL-E. I built a Visual Prompt Builder web app on Netlify (Gemini 2.5 Flash backend) as a structured prompt-engineering reference.
- CRM and workflow platforms Salesforce (Certified Associate, Trailhead Ranger on the Business Analyst path), GoHighLevel, Notion, Retool, Bubble, n8n (Railway-hosted), Make.com, Apify.
- Databases and backends Convex, Supabase (with pgvector for vector search), Postgres. I led a full Supabase-to-Convex migration across two of my projects.
- Work and collaboration Slack, Microsoft Teams, Loom, Google Workspace, Microsoft Office 365, Jira, Confluence.
- Design and content Canva, Figma, Lucidchart, Elements Cloud, Camtasia, DaVinci Resolve.
Also experienced with Cursor, Bolt, and Windsurf. And more than a few I've probably forgotten.