Content is supposed to drive leads, right? Yet too often, your blog posts and newsletters live in one silo, your CRM and sales emails in another, and you’re left copy-pasting or trying to connect the dots by hand. If you’re using Letterdrop for content ops and HubSpot as your CRM, you can actually get these tools talking—so leads don’t fall through the cracks. Here’s a no-fluff guide for B2B marketers, content folks, or anyone tired of duct-taping their funnel together.
Why bother connecting Letterdrop and HubSpot?
Let’s keep it real: if your content lives in one place and your leads live in another, you’re missing out.
- Track the right stuff. See which posts and newsletters are turning readers into leads, not just pageviews.
- Automate follow-up. Get new signups and content interactions into HubSpot workflows, so you don’t forget to nurture hot leads.
- Save your sanity. No more exporting CSVs or praying Zapier doesn’t break overnight.
But—don’t expect magic. Integration can make life easier, but it won’t fix shaky content or a messy CRM. This guide will get you up and running, with tips on what’s actually worth your time.
Step 1: Map out what you want to automate
Before you click anything, think about what you actually want integrated. Here are common (and worthwhile) use cases:
- Sync new subscribers from Letterdrop to HubSpot as contacts
- Track content engagement (who read what, who downloaded, etc.) inside HubSpot
- Trigger nurture workflows in HubSpot based on Letterdrop activity (e.g., someone downloads an eBook, gets a follow-up sequence)
Write down what matters to your team. Ignore “nice-to-haves” for now; focus on what saves you from tedious work or lost leads.
Pro tip: If your sales or marketing ops team is involved, get their input early—they’ll know what data is useful (and what’s just noise).
Step 2: Check your Letterdrop and HubSpot plans
Not every feature is available on every plan. Here’s what you need:
- Letterdrop: You’ll need access to integrations (usually on “Business” or above). Their support team is refreshingly honest—if you’re unsure, just ask.
- HubSpot: The free CRM works for basic contact sync, but you’ll want Marketing Hub (Starter or above) for workflows and detailed tracking.
If you’re on lower tiers, double-check what’s included. No point in setting expectations for automation you can’t actually run.
Step 3: Connect Letterdrop to HubSpot
This is where you wire things up. The process is straightforward, but a few gotchas can trip you up.
3.1. In Letterdrop
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Go to Settings
In your Letterdrop dashboard, find “Integrations” or “Connected Apps.” -
Choose HubSpot
Click “Connect” next to the HubSpot logo. -
Authenticate your account
You’ll be redirected to HubSpot. Log in and pick the right portal/account. Grant Letterdrop the permissions it requests (usually contact management and workflow access). -
Confirm connection
You should see a “Connected” status back in Letterdrop.
What can go wrong?
- If you’re not an admin in HubSpot, you won’t be able to authorize integrations. Get someone who is.
- If you have multiple HubSpot accounts, double-check you’re connecting to the right one (not your personal sandbox).
3.2. In HubSpot
You don’t need to install anything extra in HubSpot—Letterdrop manages the integration. But check:
- Contact Properties: Make sure you know which fields Letterdrop will use (like “Source” or tags for content engagement).
- Workflows: If you want to trigger automations, make sure you have workflows set up and the right permissions.
Step 4: Set up what syncs (and what doesn’t)
This is where most people overcomplicate things. Start simple:
4.1. Sync new subscribers
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In Letterdrop:
Set new newsletter signups or gated content downloads to push contacts into HubSpot, using the integration settings. You’ll often map form fields (name, email, company, etc.) to HubSpot properties. -
In HubSpot:
Check that new contacts are showing up as expected. They should have the right properties populated—no mystery fields.
Pro tip: Set a unique “Source” or “Lifecycle Stage” for Letterdrop leads, so you can segment them later.
4.2. Content engagement data
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What works:
Letterdrop can send content interaction data (e.g., “downloaded Whitepaper X”) to HubSpot as custom properties or timeline events. This is gold for sales teams who want to know what prospects care about. -
What to ignore:
Don’t bother syncing every pageview or click. Focus on high-intent signals—downloads, signups, or repeated engagement.
4.3. Triggering nurture workflows
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In HubSpot:
Build workflows that start when a new Letterdrop contact is created, or when they hit a key milestone (e.g., downloaded an eBook). -
In Letterdrop:
Some plans let you tag or segment contacts based on behavior—use these tags to fire the right workflows in HubSpot.
Step 5: Test the integration (don’t skip this)
Before you unleash this on real leads, run a few test signups and downloads:
- Use a test email (not your main work email) to sign up via Letterdrop
- Make sure the contact shows up in HubSpot with the expected data
- Trigger a test workflow—see if the right emails or tasks get sent
Watch for: - Duplicate contacts (usually a mapping issue) - Missing data (fields not mapped correctly) - Unwanted triggers (e.g., everyone gets dropped into the same nurture, even if not qualified)
Pro tip: Do this with someone from sales or marketing ops if possible. They’ll spot issues you might miss.
Step 6: Build a simple dashboard
There’s no point syncing all this data if you can’t see what’s working. In HubSpot, build a basic dashboard to track:
- Number of Letterdrop-sourced contacts created
- Engagement rates (opens, clicks, conversions) from those contacts
- Deal creation or pipeline movement for Letterdrop leads
Skip the vanity metrics—focus on what actually drives pipeline.
Step 7: Keep it tidy and iterate
Two things to watch:
- Data hygiene:
Over time, integrations can get messy. Set a calendar reminder to review fields, tags, and workflows every quarter. - Feedback loop:
Meet with sales/marketing monthly to see if Letterdrop leads are actually converting. If not, tweak what you’re syncing or how you’re following up.
Don’t automate just to automate. If something isn’t helping you close more business or save real time, cut it.
Honest takes and real-world tips
- Integrations break. APIs change, tokens expire, people switch tools. Keep an eye out and don’t assume it’ll “just work” forever.
- Don’t sync everything. More data ≠ better results. Sync what sales and marketing will actually use.
- Letterdrop support is solid. If you hit a wall, their team is generally responsive and will tell you if something’s not possible (instead of giving you the runaround).
- HubSpot quirks:
Sometimes, custom properties or workflows don’t trigger as you expect. Test new automations in a sandbox account if you can.
Wrapping up
Connecting Letterdrop to HubSpot isn’t magic, but it is practical—if you keep things straightforward. Start with the basics: sync real leads, track meaningful actions, and automate only what you’ll actually use. Don’t get lost in the weeds or chase shiny features.
Keep it simple, run regular checks, and improve as you go. You’ll spend less time wrangling CSVs and more time actually nurturing the leads your content is bringing in. That’s time well spent.