Pricing models are evolving in the age of AI. Legacy billing and CPQ systems are being pushed beyond their core designs and are struggling to keep pace with new models. This does more than just slow teams down. It erodes customer trust and blocks teams from testing new (and better) monetization models.
My friends at Metronome unpacked why billing has become the operating system for revenue along with how leading companies are adapting. Discover a modern approach to pricing, billing, and growth in the AI era here.
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We need to talk about the personal emails plaguing our signup forms.
Personal emails have become a ubiquitous annoyance for free funnels, demo requests, events, and lead magnets. We’re usually left with two (bad) choices to deal with them: either block personal emails entirely or allow personal emails and then exclude these from reporting. Both approaches assume personal emails are essentially worthless.
This isn’t a new issue, to be clear. People have signed up with personal emails for as long as there have been form-fills. But the personal email problem seems to be getting (much) worse.
At vibecoding darling bolt.new, for instance, 98% (!) of signups come from personal emails. That isn’t a typo. My conversations with growth leaders have revealed that AI-native products see about 75-90% of signups are personal emails.

What’s changed:
There’s tremendous pressure for teams to experiment with AI, and users are signing up with their personal emails to experiment with tools while avoiding procurement or compliance hassles.
The lines are blurring between personal and professional uses of AI with many trying AI products as consumers and then bringing them to work (ex: ChatGPT).
Social logins (ex: start free with Google) are everywhere, making it easy to create an account with one-click – usually with personal emails.
But personal emails are far more valuable than you’d expect – if you’re able to de-anonymize them. And de-anonymizing personal emails has gotten way more accurate and way less expensive than it used to be. I’m going to walk you through exactly how to turn personal emails into your next biggest pipeline source.
The personal email opportunity
I’ve previously featured the growth story of bolt.new, which spent seven years struggling to stay alive and then struck gold with an AI app builder. The startup is now at over $50M ARR and adds 20,000+ signups per day. They’ve been doubling down on enterprise and are adopted by three-in-four of the Fortune 500.
The tricky part: 98% of user signups are from personal email addresses. Many of these signups are from folks at large enterprises and simply trialing the product before going through procurement. The team wanted to identify these opportunities early so they could run more targeted GTM plays.
They ran the enrichment through Freckle, a next-gen data enrichment provider, and unlocked a goldmine: $1.7M of B2B pipeline in the first four weeks. 23% of bolt.new’s B2B pipeline now comes from personal email users.
There’s been an AI wave reaching more and more product categories. While these categories are seeing hyper-growth today, they’ll need to convert signups to become stickier and higher-value B2B customers if they want to avoid crippling AI churn. Many people are trying multiple products in a category before choosing their preferred vendor, and there’s a race to identify the best-fit prospects and win them over before a competitor does.
What’s less well known is that the enrichment rate on personal emails has seen a step-function improvement over the past year. Many PLG SaaS companies tried enriching their personal email signups in the past only to give up: the juice wasn’t worth the squeeze. These companies usually didn’t see enough coverage or the unit economics on enriching personal email signups didn’t make sense.
Because the volume of enrichments is so high, companies need to make sure the amount they spend on someone who’s not a good user (let’s face it: most personal email signups) is justified by the amount they spend on those who are. This math is finally adding up.
How to de-anonymize personal emails
De-anonymizing personal emails could be done in-house (DIY solutions) or outsourced to a purpose-built tool. The steps look something like this:

Import user sign-up data from your data warehouse (Snowflake, BigQuery etc.) into a workflow automation provider.
Potential tools: Freckle, Clay, Make, n8n
Schedule the imports every 5 minutes to be able to quickly act on the enrichment
Run a check to see if the email is educational, personal, or business.
This could be done via DIY calculations or is built-into existing tools like Freckle or Clay
If it’s a business email, extract the company domain from the email address
Most companies will choose not to act on educational email signups given that these are most likely students
Run a reverse lookup to find the LinkedIn profile using an enrichment waterfall.
The benefit of a waterfall approach is that it can check across multiple providers to maximize the match rate
Potential data providers: ContactOut, Aviato, FullEnrich, The Swarm, Reverse Contact
Enrich the company based on this LinkedIn profile.
Pull in the company domain, headcount, and industry
Enrich the contact to determine their function and seniority.
This should be done only if certain headcount and industry conditions are met in order to keep costs down
Score the lead against ideal customer profile (ICP) criteria and/or target account list.
This could be based on simple criteria available via data providers (ex: industry, headcount, tech signals, growth signals) or could be scored by AI agents with custom properties (ex: based on web scraping or other workflows)
The goals of this are two-fold: prioritizing leads and collecting intent signals for more tailored outreach
Push to CRM with enriched data
Recommend only pushing qualified leads (ex: Tier 1 and 2 leads) so the sales team is focused on the best opportunities
Enroll in automated campaigns via email or LinkedIn, as appropriate
Route to reps with assigned tasks
Trigger automated account research, as appropriate, for greater personalization
Book meetings with Tier 1 accounts.
The steps above are purposefully vendor-agnostic. More sophisticated GTM teams could DIY this with a workflow automation tool (ex: n8n, Make) and tailor the workflow to their exact specifications. The downsides would be the opportunity cost along with the ongoing maintenance of the workflow (API rate limits, complex waterfalls, managing connections with external data providers). Others may opt to run this workflow via a more GTM-specific automation tool like Freckle or Clay.
Freckle founder and CEO Nathan Merzvinskis tells me that North America-focused companies see a personal email enrichment rate of about 55%. Companies with global user bases see a lower rate of about 45%. The accuracy is usually quite high (95%+) when an email is successfully enriched.
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Proven GTM plays to turn personal emails into pipeline
OK, now the fun part: acting on the data to generate pipeline without being (too) creepy. I asked Nathan which GTM plays are working for Freckle’s customers and added a couple of my favorites as well.
GTM play 1: Outbound comms to engage user as a B2B opportunity

A basic play is simply to start enrolling ICP-fit personal users into outbound comms across email and LinkedIn. There’s a risk that these messages come across as “creepy” – after all, the user chose to sign up with their personal email and may want to stay anonymous. Getting this right all comes down to the delivery.
I’d go with a sales-assist motion here, offering to help users get the most out of the product. If someone bites and schedules a meeting, the rep can then shift into light discovery and qualification around a potential enterprise opportunity.
I personally like to adjust the outbound comms depending on the product readiness. Product signals you might consider:
Usage frequency (repeat user with regular engagement)
Usage growth (spike week-over-week or month-over-month)
High-value features (adopts more premium features like integrations)
Collaboration (has adopted social features in the product)
High-value website activity (views the pricing page, views enterprise customer stories)
Call-to-actions (clicks to request a demo, asks to talk to support)
Those with a strong ICP fit and strong product signals should be prioritized by sales first: these product qualified leads are the low-hanging fruit. Those with strong ICP fit but weak or no product signals likely require a different approach including a persona-based nurture cadence or an onboarding assistance offer.
GTM play 2: ABM to user’s colleagues & educate user on collaboration

The next level is to run account-based marketing to the user’s colleagues, driving more product adoption within target accounts that already have at least one existing user. These automated campaigns would include targeted ads via LinkedIn or Meta along with automated lifecycle campaigns via email to the initial user. A typical hook: collaborating with colleagues who are already using the product.
GTM play 3: Identify and action on multi-threaded accounts

It’s not uncommon for an account to have multiple users, some of which have signed up with a personal email and others of which have signed up with work emails. The goal is expansion – rolling up the individual users into a team-wide or Enterprise plan.
These accounts are clearly product-qualified; however, there’s real work to multi-thread to ultimately link accounts. This data should be surfaced to the rep who owns the account and users should get enrolled in a collaboration-based lifecycle campaign.
GTM play 4: Identify and action on multi-threaded accounts

Multi-threading accounts may pose a challenge if existing users aren’t the actual buyer or decision-maker. The next step is to find the likely decision maker(s) and go top-down. This is effectively intent-based outbound where the intent signal is existing product usage within the account.
The message might look something like this:
Hi X - Your team has 4 users and 23 active tables in Freckle across two different accounts.
Thought I’d reach out, as by consolidating those accounts you’ll be able to get a lower cost per credit and better team visibility on what’s being enriched - avoiding records being enriched twice!
Do you have 15 mins to chat about this next week? Will be great to connect and help you unlock more value from Freckle.
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I’d recommend enriching a test batch of your personal email signups to validate that these include high-value accounts within your ICP and that these can be enriched at a viable cost-per-lead. If that checks out, start with the first GTM play. Measure responses to the outbound campaigns (opens, replies, meetings booked) and conversion to qualified pipeline.
Assuming the first GTM play checks out, shift toward more complex plays and greater automation. Engaging peers, multi-threading accounts, and going top-down are more time- and resource-intensive. But they can also unlock net-new demand from your dream customers. And it could be what turns personal emails into your next biggest pipeline source.
Additional resources

