Founding Director,
AI Digital Strategy
You drive measured results for clients, and you're done watching your agency treat AI as a pilot. Come own the strategy layer of every engagement, direct a fleet of AI agents through the production work, and build an entirely new kind of agency from the ground floor.
About Lynton
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 the partnership to build what comes next.
We build measurement-first websites on open-source stacks that companies own, while we help them operate. Websites that use AI as the new CMS, load in under a second, show up when customers ask an AI where to buy or book, and prove what they produce in revenue. We're AI-native in how we operate, not only in what we sell, and we're building the agency we'd want to work for, from the ground floor.
The opportunity
You excel and thrive with this kind of work. You've driven measured results for clients: pipeline, bookings, revenue, not just deliverables. You've led the work, and probably the people. And you're done watching your agency treat AI as a pilot project while it rewrites how the whole business gets done.
Here, AI is the operating model. As our founding strategy leader, you own the strategy layer of every engagement: the assessment and roadmap phase that opens each project, the measurement framework that proves what the work produced, and the marketing-and-sales strategy that grows a launch into an ongoing engagement. You expand client accounts with new projects and solutions. You direct a fleet of AI agents through the production research and reporting, so your hours go to judgment and client leadership instead of throughput. You build the playbook and the frameworks from a blank page, and the team behind them as we grow.
A lot of that work is helping clients leave tools they have outgrown. You scope and lead migrations off legacy platforms (CRM, Marketing Automation, website CMS), and design the autonomous agents and AI automations that replace the workflows people used to hand-build. If you have spent years implementing and migrating client systems, this is where that experience compounds instead of repeating.
This is a ground-floor seat. If you manage a team today, you'll be trading that team for a blank slate and an agent fleet. You'd swap managing headcount for building something. For the right person that reads as the appeal, not the sacrifice.
What you'll own
- ▸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.
Day one, the team you direct is the agent fleet. As engagements compound, you build and lead the human strategy bench behind you: hiring, standards, review. You're the person the strategy function grows around.
Who you are
- ●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.
Bonus
- +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
What "AI-native" means here, concretely
- ▸Agents are teammates with roles and functions, not tools you occasionally open. You direct them.
- ▸Engagements ship with an AI inference budget as a line item. You manage it like any other resource.
- ▸AI runs the production research and reporting a whole pod would handle elsewhere, so you operate at the level of judgment and client leadership instead of throughput.
- ▸We build for ourselves first. The stack, agents, and measurement we sell are the ones we run our own business on. We write about it publicly as we go.
First 90 days
- 1–3Weeks. Co-run a live Strategy and Blueprint phase (estate assessment, stack assessment, stakeholder sessions, measurement-definitions workshop) and lock the roadmap at exit.
- 4–10Weeks. Own the measurement build alongside design and build: definitions, then tracking plan, then dashboard spec. Draft the near-me and AEO visibility scorecard across the client's locations.
- 60–90Days. Bring the marketing-and-sales growth conversation: a channel and pipeline plan for the client's budget shift, priced as ongoing work. And start shaping the strategy playbook the next hire will run.
Why this role
- Ground floor with credibility. Not a zero-traction startup: 27 years in business, 16 years of enterprise relationships, a legacy client base generating revenue, and a market thesis the numbers are proving right. You build the new agency on top of a real foundation.
- Build the playbook, then lead it. You will inherit and build upon the assessment frameworks, the measurement methodology, and the AEO practice, productize them so agents run them in a fraction of the hours, then lead the bench that scales it.
- Own the outcome, not a lane. You own strategy from the first assessment through the reported revenue result and the expansion that follows. No layers, direct to leadership.
- Real leverage. You direct an agent fleet on the production work. This is what AI-native feels like from the inside, the thing your current agency keeps promising and not delivering.
No cover letter.
Just signal.
Four short questions designed to surface what a resume can't. We want the results you've driven, how you've led, and how you actually work with AI today.
A real person reads every application. We use AI to help us keep up and summarize what you send, but the hiring decisions are ours. Specific answers beat polished ones.
If it's a fit, expect a conversation with the CMO and the founder, then a working session on an example engagement. We hire on substance, expertise, and long-term growth potential.