Founding Director, AI Digital Strategy

Lynton • Quinte West, ON

6d

About The Position

Lynton spent 16 years as a HubSpot partner: 2,000+ projects across 50+ industries. We know SaaS and agency work from the inside. When we saw what's coming with AI, we left HubSpot to build what comes next.
We build and run AI-native growth systems for mid-market companies: measurement-first websites, the sovereign stack that replaces legacy software, and AI agents we deploy to run the marketing, sales, and operations that used to live in hand-built workflows. The client owns the infrastructure, we operate the agents, and the whole system proves what it produces in revenue. We're AI-native in how we operate, and we're building products, solutions, and a whole new kind of company from the ground up.

Requirements

• 8+ years driving measurable results for clients in digital marketing and sales strategy. The number you point to is revenue, pipeline, or bookings you moved, not deliverables you shipped.
• Agency-grown. You've built your career inside agencies. You know the model from the inside (the pod, the billable hour, the retainer treadmill) and you can see where AI breaks it open.
• You have worked inside clients' stacks. You have implemented, integrated, and migrated marketing and CRM systems for clients, so you know what breaks in a migration and how to de-risk a cutover. HubSpot ecosystem depth is a strong plus given our client base and history.
• You've led. You've run a team, a client pod, or major engagements end to end and answered for the outcome. Or you're the senior everyone already treats as the lead, and you're ready for the title. Experience or clear potential both count.
• Deep analytics fluency: GA4, GTM, conversion tracking, attribution modeling, dashboard design. You've built measurement frameworks, not just read the reports.
• Local SEO depth, plus real curiosity about AEO and AI search. You can explain llms.txt to a VP and defend why it matters.
• Frustrated in the right way. You're doing well where you are and could stay. What's pulling you is watching your agency treat AI as an experiment while you can see it changing the whole business.
• Ready to build, not just manage. If you run a team today, you're ready to trade it for a blank page and an agent fleet, and build a function (eventually a cross-functional agency team) from the ground floor.
• AI-first in practice. You already work with AI agents or LLM-driven workflows day to day. You can spec a task, judge the output, and improve the loop. Directing agents through the production work is the appeal, not the threat.

Nice To Haves

• Hands-on paid-media management
• Booking or e-commerce funnel optimization
• RevOps or CRM/martech implementation and migration experience
• Replacing legacy workflow automation with code or AI agents
• Familiarity with modern open-source web stacks

Responsibilities

• Strategy and blueprint phases. Lead the phase that opens every engagement: digital estate assessments, technology-stack assessments, stakeholder sessions, and phased roadmaps with budget allocation. You produce decision-ready packages leadership approves with confidence.
• Systems adoption and migration. Lead clients off tools they have outgrown and onto AI-native infrastructure: scope the migration, design the autonomous agents and AI automations that replace brittle workflows, and own the cutover plan. You set the architecture and direct the build team and agents on execution.
• Measurement frameworks that prove revenue. Run measurement-definition workshops with client teams: what counts as a lead, how revenue attributes across marketing and sales, which offers run web-only so redemption proves attribution. Establish baselines, define the dashboards, own the monthly story.
• Marketing and sales strategy. Funnels, conversion, promotions and campaign systems, lifecycle and abandoned-intent recovery, and the handoffs where marketing becomes pipeline and pipeline becomes revenue. You define what the systems need to do; the build team makes them do it.
• Search and AEO. Own organic and local SEO across multi-location businesses and answer-engine optimization. Our own migration grew AI-referred traffic about twelvefold, and you'll build the practice that produced it into a repeatable capability for clients.
• Paid-media readiness and advisory. Own the tracking foundation and advise clients shifting budget to digital: ROAS targets, channel mix, what to spend where once the numbers are trustworthy. This is the expansion lane, where you grow launched projects into ongoing engagements.
• Client leadership. Present to VPs and executives and earn the decision. Translate one plan into per-stakeholder outcomes across marketing, sales, search, and the executive team. Surface the next phase at the moment the data justifies it.
• AI-first delivery. Direct our agent fleet on strategy work: audits, competitive research, content and funnel analysis, reporting. Manage the per-engagement AI inference budget like any other resource. Build reusable agent workflows so every engagement makes the next one faster.
• Agents you deploy for clients. Beyond the internal fleet, you scope, build, and operate AI agents on the client's behalf: running their ads and campaigns, qualifying and routing leads, handling lifecycle and support, keeping their reporting current. These are recurring engagements you own and grow, not one-time projects.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed