Jonathan McLemore
5.0
(10)
AI Strategy Expert | Transform with Proven Enterprise Solutions
Studied at Ryerson Polytechnic University
Works at VersaFile
Successful clients at
Available Thursday at 1:30 PM UTC
Questions? Start chatting with this coach before you get started.
Jonathan's Coaching Offerings
Custom hourly · $175/hr
Get help with AI Readiness Assessment, AI Strategy, and .
Jonathan’s AI Strategy & Transformation Qualifications
Experience level: Manager
10+ people coached for AI Strategy & Transformation
Here to be an asset! I'm the Founding Solutions Engineer for Plinko Solutions, an AI automation agency that helps lean service businesses eliminate manual data entry and sales bloat. I'm also one of the few Leland OpenClaw vendors, secure and reliably here for you! I actively live the dual life of a service agency founder and a GTM strategist bringing Ai into the market meaningfully. I know firsthand how to balance client delivery, technical sales, and product development without burning out or bloating your headcount. My unique background blends deep technical expertise (TypeScript, Docker, cloud deployment) with professional real estate experience as a licensed Ontario realtor. This means I understand both how to build complex systems and how to sell them to traditional, non-tech industries. If you are looking to launch an automation agency, build a B2B SaaS product, or figure out how to sell technical solutions to service businesses, I can guide you through the exact playbooks I am using today.
Jonathan can help with:
AI Readiness Assessment
AI Strategy
AI Roadmap Development
AI Agents
AI Policy & Governance Design
Team AI Upskilling
AI-Driven Sales
Jonathan also coaches for AI for Sales & Marketing and AI Automation & Agents. View all.
About Jonathan
Hello! My mission is to empower businesses by making AI and automation accessible. Right now, this lives in the pulse of open source community (i.e. being a secure OpenClaw vendor) Accessibility is my heart’s mission. The best of technology should be accessible by many hands through empowering pre-sales education and agentic sales infrastructure. Being dual citizen U.S./Canadian, raised in a West-Indies household, I’ve been close to the gaps in both my career and personal life. I’ve spent the last decade in tech in many facets. From December 2022 forward, I’ve been building solutions using AI and no code automation. My experience is painted across the canvas of digital marketing, sales (prospecting), technical recruitment, and sales management (end-to-end client management). Walking across this bridge of novel frontier is what brings me into my line of work, day in day and day out with joy.
Why do I coach?
I believe the best of mankind is for all of mankind. These new capabilities that artificial intelligence brings to the table can bridge the brave or block the fearful, it really comes down to how well you understand your future state and goals. I believe that with determination, digital literacy can be and should be multiplied into as many hands as possible. This sort of leverage empowers and lifts communities through amplified leverage, experienced both personally and professionally. Launching an Ai and Automation agency has changed my life spark by spark, and I'm excited to share the lightbulb moments with you.
Work Experience
Enterprise Customer Success Manager
VersaFile
January 2026 - Present
We help people with their information, particularly in highly regulated industries. Our mission is to get that information to the right person, at the right place, at the right time. --- Completed structured enablement through M-Files Academy, earning certifications across core platform competencies to support enterprise ECM implementations: • M-Files Essentials Certification – Foundational metadata structure, vault navigation, and information architecture principles for document management deployments • M-Files User Certification – End-user workflows, version control, permissions management, and day-to-day ECM operations across Desktop, Web, and Mobile • M-Files Business Administrator Certification – Metadata configuration, workflow design, permissions architecture, and vault administration for regulated-industry environments • VersaFile Solution Training – Intelligent content and process automation frameworks for enterprise organizations in highly regulated industries (healthcare, finance, legal, manufacturing) • Enterprise Content Management (ECM) Enablement – Document lifecycle management, records management, compliance workflows, and information governance aligned with ISO and SOC standards • M-Files AI & Intelligent Information Management – AI-powered context-first document retrieval, automated metadata tagging, and intelligent search configuration • Completed SAP Learning training in SAP Integration Suite, SAP S/4HANA Fundamentals, and SAP Document Management — enabling client success across ECM deployments in SAP-integrated enterprise environments.
Founding Solutions Engineer
Plinko Solutions
November 2024 - Present
• Own end-to-end solution delivery for 3–5 active client accounts through requirements gathering, solution design, implementation, and post-launch support, delivering enterprise integration of CRM systems, API workflows, and automation solutions—bootstrapped to profitability within two months. • Lead structured discovery and requirements-gathering sessions to document workflows, identify system integration gaps, and translate findings into scoped 14-day implementation plans for no-code/low-code automation solutions (Make.com, HubSpot) across lead routing, CRM workflows, data pipelines, and business process automation. • Delivered $24,000 in additional revenue in three weeks for a SAP-integrated recruitment firm by designing and implementing API-driven automation workflows and CRM integrations that reduced manual handoff and accelerated sales pipeline velocity and lead management processes. • Built AI-driven workflow automation and email classification workflows integrated into CRM systems, improving operational throughput and recovering approximately $18,000 in closed contract value for an events management company through workflow optimization and process automation. • Designed and implemented enterprise-grade CRM-integrated solutions using REST API connections, webhook configurations, system integrations with Make.com and HubSpot to automate lead routing, follow-up workflows, and data synchronization across multiple SaaS platforms, reducing manual admin by 60%+ and accelerating lead response times.
Private Educator
Birmingham International Collegiate of Canada
September 2025 - January 2026
- Design and deliver differentiated Grade 12 lessons for private students, aligning instruction with curriculum expectations and post-secondary readiness goals - Translate complex concepts into scaffolded, step-by-step learning experiences, including inquiry tasks, exam prep sessions, and targeted review for unit tests and final evaluations - Model responsible AI use in the classroom—teaching students how to use tools like MagicSchool ethically, verify information, and avoid plagiarism while building AI literacy - Use formative and summative data (quizzes, exit tickets, AI-assisted rubrics) to adjust instruction, close skill gaps, and provide timely feedback to students and parents
Sales Manager
Zown
May 2024 - September 2024
• Managed the end-to-end client sales funnel while building and coaching a team of four sales reps, ensuring consistent pipeline coverage, follow-through, and process adherence. • Led 8–12 daily 30-minute consultation calls to qualify prospects, explain program and payment options, and consistently exceed targets for follow-ups and funded deals (placing at least two families in new homes per month). • Improved client retention by 60% by optimizing HubSpot CRM pipelines, email sequences, and follow-up cadences.
Business Development Manager
RE/MAX Success Realty
January 2024 - June 2024
• Partnered with senior leadership to align agent recruitment and client acquisition initiatives with brokerage growth objectives. • Developed and executed marketing materials and campaigns to attract new clients and real estate agents. • Trained agents and staff on deal administration and SaaS tools including LoneWolf, BrokerBay, kvCORE, Constant Contact, MAXCenter, and Realty Software. • Supported recruitment efforts to identify, attract, and onboard top real estate talent, contributing to 1–2 new agent placements per month.
Education
Humber College
Real Estate License, Real Estate
2024 - 2025
Licensed under RECO (Ontario, Canada)
Ryerson Polytechnic University
English (Honours), English
2018 - 2023
10 Reviews
Overall Rating
5.0
Jonathan has helped Leland clients get into Plinko Solutions