What exact step-by-step playbook does a b2b startup need to convert freemium users into £100k annual customers with Intercom

I remember the first time I saw a freemium sign-up spike and realised that growth alone wouldn't pay the bills. Freemium is a brilliant top-of-funnel driver, but turning those free users into high-value customers — the kind that bring in recurring £100k ARR accounts — needs a repeatable, data-driven playbook. Below I walk you through the exact step-by-step playbook I use, built around Intercom, to convert freemium users into enterprise-calibre customers.

Why Intercom?

I pick Intercom because it combines real-time messaging, automated campaigns, user segmentation and product tours in one platform. That allows a single workflow to nurture users from initial activation to high-touch enterprise sales handoff. You could piece together other tools, but Intercom reduces friction and centralises user context — which is crucial when you're trying to scale conversions to large accounts.

Step 0 — Define the £100k Customer Profile

Before automating anything, I clearly define what a £100k annual customer looks like for my product. This profile informs targeting, messaging, and PRICING options.

• Company size: e.g. 200–2000 employees
• Industry: e.g. fintech, SaaS, retail chains
• Use case complexity: requires custom integrations, onboarding and SLAs
• Decision-makers: Head of Ops, CTO, VP Product
• Willingness to pay: needs multiple seats, advanced features, and support

Everything that follows maps back to this ICP (ideal customer profile).

Step 1 — Instrumentation & Tracking

I instrument every meaningful event and property in Intercom and my analytics stack (Mixpanel/Amplitude + Stripe). If you can’t measure activation, expansion signals, and churn risk, you can’t optimise for enterprise conversions.

• Capture signup source, company size, industry, and role on signup form.
• Track product events (e.g. connect-integration, create-team, run-report) with consistent naming.
• Sync billing data from Stripe: MRR, plan, trial start/end.
• Enrich account data via Clearbit/FullContact inside Intercom for firmographics.

Step 2 — Segment Freemium Cohorts

I create targeted cohorts inside Intercom based on signals that correlate with high LTV. Instead of treating all free users the same, I prioritise those who resemble my ICP.

• High-potential cohort: company size >100, used integrations, multiple seats invited.
• Activated cohort: completed 3+ key events in first 14 days.
• Expansion-ready: active for 60+ days with repeating usage but on freemium plan.

Step 3 — Activation Flow (Product-Led Onboarding)

Activation is the single biggest multiplier. I design product tours and Intercom Messages (in-app) that guide freemium users to an ‘aha’ moment within 24–72 hours.

• Use Intercom Product Tours to create a 3-step activation path that culminates in a valuable event (e.g., created first report, invited teammates).
• Trigger an in-app message when users reach step 2 offering a short video or checklist to complete step 3.
• Email a concise welcome series for newcomers who didn't complete the tour.

Measure activation rate and time-to-aha. If the ICP cohort activates at a higher rate, prioritise that cohort for the next steps.

Step 4 — Intent Signals & Qualified Leads

Not everyone will convert to a £100k account. I set up intent-based scoring and automated qualification in Intercom so we can surface high-value leads to Sales.

• Create a scoring model using events and firmographics: product activity, number of seats, integrations, and Clearbit data.
• When score > threshold, automatically tag the account as “Sales Qualified — Enterprise.”
• Fire an internal Intercom conversation to the sales inbox with a summary card (usage, ROI metrics, key contacts).

Step 5 — Nurture Path for High-Potential Accounts

For accounts that match ICP but aren’t yet ready to talk to Sales, I create a high-touch nurture campaign inside Intercom combining automated messages and human outreach.

• Week 1–4: automated in-app messages highlighting advanced features and case studies relevant to their industry.
• Week 4–8: personalised email from a named SDR offering a short discovery call and sharing a tailored ROI estimate.
• Always offer a live product demo and a custom ROI calculator for accounts that show repeated usage but no conversion yet.

Step 6 — Hand-off Playbook to Sales

I agree on a structured handoff between Product/CS (via Intercom) and Sales. Without this, great leads slip through the cracks.

• Auto-create a conversation in Intercom when qualification score is reached; include: usage summary, churn signals, and suggested next steps.
• Sales gets a playbook: initial outreach template, demo script, custom pricing guidelines to reach £100k ARR (multi-seat, custom integration fees, SLA options).
• Track outcomes in Intercom: demo booked, proposal sent, negotiation stage.

Step 7 — Pricing & Packaging to Hit £100k ARR

To land a £100k account we need the right package. I design pricing tiers and packaging that nudge customers from freemium → paid → enterprise.

• Freemium: single user, limited integrations.
• Pro: small teams, monthly fee — focus on expansion signals.
• Enterprise (target for £100k accounts): multi-year contracts, per-seat or feature-based pricing, professional services and integrations, premium SLA.

In Intercom, I show upgrade prompts targeted by company size and activity and share tailored PDFs for enterprise proposals. I also use Intercom to schedule contract review calls directly from the app.

Step 8 — Use Success Stories & Social Proof

Enterprise buyers want de-risking. I serve relevant case studies, ROI numbers and testimonials in Intercom messages at opportune moments (after activation, before outreach, during negotiation).

• Dynamic content blocks in Intercom emails: show case study relevant to the recipient's industry.
• In-app banners with logos of customers similar to the ICP.
• An automated message offering to connect with a customer reference once negotiation begins.

Step 9 — Product-Led Expansion & Upsell Triggers

After initial conversion, I continue using Intercom to spot expansion opportunities that push accounts toward £100k ARR.

• Usage thresholds trigger upgrade prompts — e.g., invited users > 50 triggers “Scale Plan” outreach.
• Feature usage: when they start using an enterprise feature on freemium (trial), a triggered sequence offers a customised package.
• Quarterly expansion review: automated messages before renewal offering tailored pricing and roadmap alignment meetings.

Step 10 — Measure, Iterate, and Run Experiments

Everything above is hypothesis-driven. I treat every element as an experiment and measure incremental impact on qualified leads, conversion rate, average contract value, and time-to-first-enterprise-deal.

I A/B test messaging, timing, and pricing offers using Intercom’s campaign analytics and combine that with cohort analysis in my analytics stack. Small improvements compound quickly when you’re moving thousands of freemium users through the funnel.

Practical Intercom Automations I Use

• Auto-tagging and scoring based on Clearbit firmographics + product events.
• Triggered messages for usage-based milestones (e.g., “You’ve hit 10 seats — want to scale?”).
• Conditional product tours that adapt to user persona (admin vs. contributor).
• Auto-creation of support and sales conversations for high-score accounts.
• In-app Nudge to book a demo when a user spends >X minutes in advanced settings.

Freemium conversion to £100k customers is not magic — it’s systematic: define the ICP, instrument behaviour, activate fast, score intent, nurture high-potential accounts with personalised content, and hand them to a sales team armed with the right pricing and case studies. Intercom ties the threads together by keeping the conversation contextual and timely. Implement these steps, measure lift at every point, and iterate until your funnel consistently surfaces the handful of accounts that will become your £100k ARR customers.