Jonathan McLemore

Ryerson Polytechnic University
VersaFile
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Starting at 3:00 PM UTC

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I help professionals and businesses turn AI, automation, and better information systems into measurable operational and revenue outcomes. I’m a Toronto-based solutions engineer, enterprise customer success professional, and founder of Plinko Solutions. My work sits at the intersection of AI agents, CRM and workflow automation, sales infrastructure, and enterprise content management—helping teams move from scattered tools and manual handoffs to dependable systems people can actually use. Since 2022, I’ve built and implemented no-code and low-code solutions across prospecting, lead routing, CRM workflows, API integrations, content operations, and AI-assisted processes. Through Plinko Solutions, I’ve delivered client automation projects that improved pipeline velocity, reduced administrative work, and generated meaningful recovered and incremental revenue. Today, I also support regulated-industry organizations with information governance, document workflows, metadata, and intelligent information management. My background spans B2B sales, technical recruiting, customer success, marketing, client management, and education. As a dual U.S.–Canadian citizen raised in a West Indian household, I care deeply about making powerful technology understandable and accessible—not just available to people with technical backgrounds.

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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.

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

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.

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.