Role Proposal · Marketing Org
Automation Programs Lead,
Marketing
Jackson Sherwood — reporting to Tyler
Over the past six months, I've built the automation systems, run the enablement sessions, and closed the AI adoption gaps across HCP Marketing. This isn't a pitch for something new — it's a proposal to formalize what's already working and put a name on the person responsible for scaling it.
Active · Already running
Reporting to: Tyler
No new headcount required
Q2 2026
AI systems live
3
shipped & maintained solo
Sub-orgs enabled
6+
pmm · events · seo · lifecycle · more
AI sessions led
10+
1:1s · team sessions · new grad onboarding
The Situation

In mid-2025, I transitioned from Events to test an open question: could AI fundamentally change how the marketing team operates? The answer is yes — and the evidence is already in production.

I am co-creating the Marketing AI Accelerator with Tyler and Manu. I built the Counter-Intel system solo — daily competitive monitoring that surfaces changes to Slack every morning with a weekly cross-functional digest. I've run 1:1 enablement with Chris Root and Karissa Satala, led PMM team sessions, and onboarded new AI graduate hires. Other teams are requesting access.

This proposal formalizes that scope.

What Breaks Without This
⚠️
The AI Accelerator stalls
Without a dedicated owner, the program Tyler and Manu commissioned stalls the moment this gets deprioritized. No one else is running it.
⚠️
Automation systems require active ownership to keep delivering
The systems in production — Counter-Intel, digest pipelines, workflow templates — require ongoing maintenance and iteration. Without a dedicated owner, they degrade and stop surfacing useful output.
⚠️
Marketing AI adoption stays uneven
Teams that haven't been reached continue figuring it out on their own — or don't. No one is accountable for closing that gap.
⚠️
Marketing's AI fluency needs institutional ownership to compound
The automation capability built here is currently person-dependent. Formalizing this role creates a permanent center of gravity for AI fluency across the marketing org — the programs, templates, and systems belong to the team, not just one person.
Proof of Work
HCP Reviews Prototype → Live Product · 100%+ YoY Growth
business impact
Built the Reviews prototype in Lovable — no engineering, no PM scoping. Product took it to production. The desktop referral program that followed grew 100%+ YoY.
Lovable Rapid prototyping Product handoff
Marketing AI Accelerator
in progress
Co-created with Tyler and Manu. Structured program to upskill the marketing org on AI — prompt engineering, MCP setup, and workflow automation across all sub-orgs.
Claude Code MCPs Curriculum design
Counter-Intel System
live
Built solo. Daily monitoring across 60+ pages in 8 verticals — crawls competitor sites, runs Claude AI analysis, posts changes to Slack with before/after screenshots. Weekly digest distributed cross-functionally.
n8n Claude API Supabase Firecrawl Slack
Cross-team AI Enablement
ongoing
1:1s with Chris Root (MCP setup, AI workflows) and Karissa Satala (custom tooling + Claude Code onboarding). Led PMM team sessions on Claude Code, prompt engineering, and workflow automation.
Consulting Workflow audit MCP setup
New AI Graduate Onboarding
ongoing
Onboarded new AI graduate hires onto Claude Code, MCP setup, and HCP's internal workflow patterns — structured tracks so new hires contribute faster.
Claude Code MCP setup Curriculum
What This Role Owns
AI Accelerator Program
Architect and run the marketing team's AI upskilling program end-to-end. Curriculum, sessions, tracking, and cross-functional rollout. This is Tyler's initiative — this role ensures it doesn't stall.
🤖
AI Systems & Automation
Build, ship, and maintain AI-enabled systems across marketing. Counter-Intel, digest pipelines, data workflows, and new tooling as the org's needs evolve. Systems that run while you sleep.
🔁
Cross-team Enablement
One-on-one and group sessions across PMM, Events, Community, SEO, Lifecycle, and beyond. Audit each team's workflows, identify AI leverage points, and ensure adoption sticks — real tasks, not demos.
📦
Tooling, Templates & Prototypes
Build high-fidelity prototypes, reusable n8n templates, and internal AI tools that teams can fork without engineering support. Owns the path from prototype to production-grade tool behind Okta SSO.
2Q26 OKRs — Already Submitted

These are my actual Q2 OKRs under the AI-Enabled GTM theme. The role being proposed here is the person accountable for delivering them.

OKR 1
100% of HCP Marketing proficient in core AI workflows — every marketer uses at least one automated workflow daily. AI Accelerator curriculum complete, all sub-orgs reached. 3+ reusable templates published.
OKR 2
Counter-Intel operational and cross-functional — 90%+ of PMMs using alerts weekly, 60+ pages monitored, digest going cross-functional. 2+ non-marketing teams running active workflows.
OKR 3
Transition HCP prototypes into production-grade tools — 3+ AI-powered tools live behind Okta SSO by end of Q2.
OKR 4
Reusable automation templates available org-wide — 3+ n8n workflow templates any team can fork without engineering support, with documented setup guides.
90-Day Execution Plan
Days 1–30
Formalize & Launch
Finalize AI Accelerator curriculum. Expand Counter-Intel to 60+ pages. Ship email digest cross-functionally. Complete new AI grad onboarding tracks.
Days 31–60
Expand & Enable
Stand up Counter-Intel for 2 non-marketing teams. Run hands-on sessions with each marketing sub-org — real tasks, not demos. Publish 3+ reusable n8n templates. Define prototype → production path with engineering.
Days 61–90
Measure & Productize
Confirm 90%+ PMM Counter-Intel adoption. Verify 3 AI tools in production behind Okta SSO. Publish 3 workflow templates. Deliver Q3 AI enablement roadmap.
The Ask

Not a new hire. Not a new budget line. Just formalizing what's already in motion — with a title that reflects the actual scope of the work.

Market context: Glassdoor 2026 — AI Enablement median $134k, 25th pct $104k. The $110k–$120k ask is below median, anchored in data, and reflects the IC level of this role.

Title
Automation Programs Lead, Marketing
previously: no formal automation title
Reporting to
Tyler
no change to reporting line
Compensation
$110k–$120k
market median: $134k · current: $82k · Glassdoor 2026

One more thing: I'm not going anywhere. Trade show on the East Coast — I'm on the flight. Gap that needs covering — I'll cover it. This adds structure; it doesn't subtract flexibility. A generalist who builds production systems doesn't come apart.