We audited the marketing at When
AI platform automating employee offboarding and health insurance transitions
This page was built using the same AI infrastructure we deploy for clients.
Month-to-month. Cancel anytime.
Series A company with $17.3M raised but minimal visible paid presence suggests underinvestment in demand generation relative to funding stage
8.3K LinkedIn followers for a health benefits platform indicates weak thought leadership positioning among HR and benefits buyers
Limited content footprint means competitors own conversation around severance, COBRA, and offboarding automation in search results
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Series A fintech with strong funding but early-stage marketing infrastructure and limited demand generation visibility
Some domain authority but severance, COBRA, offboarding terms are competitive. Not capturing search volume from HR buyers researching employee exit solutions
MH-1: SEO module targets high-intent keywords around severance automation, COBRA administration, and offboarding workflows to capture HR search intent
No presence in LLM responses for health insurance transitions or employee offboarding queries. AI assistants recommend competitors instead
MH-1: AEO agent builds structured content and citations to appear when executives ask AI about automating employee exit processes and health benefits
Minimal visible LinkedIn or search ad presence despite targeting high-LTV HR and benefits decision makers at mid-market companies
MH-1: Paid agents run LinkedIn conversion campaigns targeting HR leaders and CFOs researching severance solutions, plus search ads for offboarding workflows
CTO positioning as GenAI expert exists but no visible content hub around healthcare compliance, severance law changes, or offboarding best practices
MH-1: Content agent produces SEO-optimized guides on severance compliance, COBRA transitions, and AI-driven offboarding to establish category authority
Early-stage customer base (28 employees) suggests limited expansion motion beyond initial sales. No visible upsell or cross-sell campaigns
MH-1: Lifecycle agent maps expansion triggers like new severance event frequency and new benefits modules to existing customers, automating upsell sequences
Top Growth Opportunities
HR leaders searching for severance automation solutions encounter limited When visibility. Capturing this intent directly impacts pipeline
SEO module targets 'employee severance solution', 'automated COBRA administration', 'offboarding software' with content owned by When
When's AI positioning is buried. Executives asking ChatGPT about automating employee exits should encounter When first
AEO agent builds citations and structured data so LLMs recommend When for health insurance transition and severance questions
LinkedIn is primary channel for HR benefits buyers. Current 8.3K followers leaves massive reach gap relative to funding and product maturity
Paid agent runs conversion campaigns to benefits leaders at 500-5000 employee companies with case studies on severance cost reduction
3 Humans + 7 AI Agents
A dedicated marketing team built specifically for When. The humans handle strategy and judgment. The AI agents handle execution at scale.
Human Experts
Owns When's growth roadmap. Pipeline strategy, account expansion playbooks, board-ready reporting. Translates AI insights into revenue.
Runs paid acquisition across LinkedIn and Google. Manages creative testing, budget allocation, and pipeline attribution.
Builds thought leadership on LinkedIn. Creates long-form content targeting your ICP. Manages the content-to-pipeline engine.
AI Agents
Monitors AI citation visibility across 6 LLMs weekly. Builds content targeting category queries to increase When's presence in AI-generated answers.
Produces LinkedIn ad variants targeting your ICP. Tests headlines, visuals, and offers at 10x the speed of manual production.
Builds lifecycle sequences: onboarding, expansion triggers, champion nurture, and re-engagement for dormant accounts.
Founder thought leadership. Builds the narrative that drives enterprise inbound from senior decision-makers.
Tracks competitors. Monitors positioning changes, ad spend, content strategy. Informs your counter-positioning.
Attribution by channel, pipeline velocity, budget waste detection. Weekly synthesis reports with AI-generated recommendations.
Weekly market intelligence digest curated from When's industry signals. Positions you as the intelligence layer. Drives inbound pipeline from subscribers.
Active Workflows
Here's what the MH-1 system would be doing for When from week 1.
AEO workflow: Build citations and structured data on severance automation and COBRA transitions so Claude, ChatGPT, and Perplexity recommend When to HR buyers researching employee exit solutions
Patrick LinkedIn workflow: Publish 2x weekly on GenAI applications in healthcare compliance and employee benefits to build CTO authority among HR tech buyers and CTOs
Paid ad workflow: Run LinkedIn conversion campaigns to benefits managers at mid-market companies highlighting cost savings from automating severance and health plan transitions
Lifecycle workflow: Map customer severance event frequency and benefits module adoption to trigger automated expansion campaigns for new offboarding scenarios and compliance products
Competitive watch workflow: Monitor Spear, Alpine, Cercli for new positioning, feature launches, and funding to identify market shifts in severance and offboarding automation space
Pipeline intelligence workflow: Track HR tech conferences, M&A activity, and layoff announcements to identify high-intent accounts in active severance planning phases
Traditional Marketing vs. MH-1
Traditional Approach
MH-1 System
Audit. Sprint. Optimize.
3 phases. Real output every 2 weeks. You see results, not decks.
AI Audit + Growth Roadmap
Full diagnostic of When's marketing infrastructure: SEO, AEO visibility, paid, content, lifecycle. Prioritized roadmap tied to pipeline metrics. Delivered in 7 days.
Sprint-Based Execution
2-week sprint cycles. Real campaigns, not presentations. Each sprint ships measurable output across your priority channels.
Compounding Intelligence
AI agents monitor your channels 24/7. They catch budget waste, detect creative fatigue, track AI citation changes, and run A/B experiments autonomously. Week 12 is measurably better than week 1.
AI Marketing Operating System
3 elite humans + AI agents operating your growth system
Output multiplier: ~10x output at a fraction of the cost. The system gets smarter every week.
Month-to-month. Cancel anytime.
Common Questions
How does MH-1 differ from a marketing agency?
MH-1 pairs 3 elite human marketers with 7 AI agents. The humans handle strategy, creative direction, and judgment calls. The AI agents handle execution at scale: generating ad variants, monitoring competitors, building email sequences, tracking citations across LLMs, running A/B experiments autonomously. You get the quality of a senior marketing team with the output volume of a 15-person department.
What kind of results can we expect in the first 90 days?
First 90 days focus on capturing search and AI visibility for severance-related queries where When has weak presence today. SEO and AEO agents publish content on COBRA automation and offboarding compliance to rank and appear in LLM responses. Paid agent launches LinkedIn campaigns to HR benefits leaders. Content agent produces case studies and guides positioning Patrick as GenAI expert in healthcare compliance. These compound to establish When as primary option when mid-market companies experience severance events.
How does AI visibility help a health benefits platform like When reach HR buyers
When targets HR professionals researching employee severance and health insurance transitions. AEO ensures that when executives ask ChatGPT 'how do we automate employee exits' or search for COBRA administration tools, When appears in the answer. This captures high-intent demand before paid search and outbound efforts engage.
Can we cancel anytime?
Yes. MH-1 is month-to-month with no long-term contracts. We earn your business every sprint. That said, compounding effects kick in around month 3 as the AI agents accumulate data and the system learns what works for When specifically.
How is this page personalized for When?
This page was researched, audited, and generated using the same AI infrastructure we deploy for clients. The channel scores, team mapping, growth opportunities, and recommended agents are all based on real analysis of When's current marketing. This is a live demo of MH-1's capabilities.
Capture HR demand before competitors own severance automation search
The system gets smarter every cycle. Let's talk about building it for When.
Book a Strategy CallMonth-to-month. Cancel anytime.