8 min read

Episode 297: Tough times, AI tools, HubSpot List tips, Sending emails to more contacts

Episode 297: Tough times, AI tools, HubSpot List tips, Sending emails to more contacts

Welcome to HubShots Episode 297: Tough times, AI tools, HubSpot List tips, Sending emails to more contacts

This edition we dive into:

  • ‘Everything’ fatigue
  • Tough economic times and the need to send more, relevant, email
  • AI tools take off - how should you respond
  • Creating random samples of contacts from lists (Segmentation)
  • Results from using Multivariate CTAs on our website (Attribution)
  • Building a View for sales reps of clients who have been sent an email from another system (Activity)
  • Last Activity date versus Last Modified date (Properties)
  • Sending an already sent email to more contacts (Activity)

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Recorded: Monday 27 March 2023 | Published: Friday 31 March 2023

Table of Contents


🌱 Shot 1: Growth Thought of the Week

Everything Fatigue

We’re seeing fatigue across many areas:

  • Subscription fatigue
  • Marketing fatigue
  • Content fatigue
  • AI fatigue
  • Community fatigue
  • Jargon fatigue

If you are feeling exhausted, you’re in good company.

More on this in upcoming episodes.

But for now, let’s discuss the immediate concerns…


Business is tough - Send more emails

If you’re finding business a little tough lately, you’re not alone - most companies (large and small) are carefully evaluating spend and strategic initiatives. Marketing and training are the first two areas to attract scrutiny - including their related tech stacks and services.

So, what to do in times like these?

I’m not a business coach, so I won’t pretend to have the answers, but I will mention an obvious reminder:

  • Communicate with your database

Most of our clients could be sending more emails

But let’s start with our own activity first…

The following is a screenshot from our XEN portal - you’ll see we’ve sent just over 140K emails so far this month.

However, our monthly limit is 930K email sends ie we’re only at approx 15% of our send capacity.

subscription limits

(You can check your own limits from the Top right account menu > Account & Billing)

Most of our emails are automated (ie part of workflows) as opposed to campaign emails (ie monthly newsletter type emails). Plus emails like the one you are reading (if you’ve received this because you signed up for our Show Notes).

Some of the automated emails are sent daily, others are sent only when certain behavioural conditions occur (eg pages being viewed). By far the majority of our emails are informational (as opposed to promotional).

When reviewing our client’s portals we’re regularly recommending sending more emails - it’s essentially free to send (compared to paid ad spend).


Relevancy versus Frequency

The only stipulation: make sure the content is relevant (we’ve discussed this many times before). Relevancy trumps frequency every time. People will happily receive an email from you every day if it adds value, and they’ll likely unsubscribe from a quarterly newsletter if it doesn’t.

Key takeaway: check your email schedule - can you create additional emails that provide value?

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✨ Shot 2: Quick Shots of the Week

Here’s a few quick items of interest we noticed:

  •   HubSpots New AI offering
    • Content Assistant to Create AI-powered content, all in one place. (YouTube video)
    • ChatSpot to get tasks done faster with AI-powered, chat-based commands. (Dharmesh’ YouTube video)
    • Built on top of GPT4
  • You can now upload images to products in the Product Library (previously you had to put in the exact URL)
  • HubSpot is still releasing bewildering ads (YouTube playlist) - what am I missing here?

Not related directly to HubSpot (but realistically this is going to impact just about every business):

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🚀 Shot 3: HubSpot Marketing Feature of the Week

Creating a List Random Sample in HubSpot (Stage 3)

A handy feature in Lists - the ability to quickly create a Random sample from your list. It’s available from the Actions menu (in the top right when editing a list):

List Random sample

It shows a form where you can select either a number of contacts, or a percentage:

Random sample

It then creates a static list with the random sample.

Very handy.

Here’s a simple use case we had recently with a client. They want to send a selective survey to a segment of their database and asked us to prepare a list of 3000 contacts to send to. We used an Active list and then tweaked the create date range of the contacts to select the requested 3000. But if we’d had this Random Sample option it would have been much simpler!

Results so far from using a Multivariate CTA on our site (Stage 4)

On our XEN home page and throughout the site we’re testing tiny tweaks to our main CTA button.

Talk to a Strategist

We’re using a Multivariate CTA with the following variations:

  • Variation A: TALK TO AN ADVISOR
  • Variation D: Talk with an Advisor

Notice that they all use the word ‘Talk’, but switch the type of person you’ll talk with. We also put in a 4th variation to test case and the word ‘with’ instead of ‘to’, just for fun. Here’s the results so far (it’s been running a month or so):

multivariate CTAs results

Summary so far: very little difference between them - and given there are only 10 submissions related to this CTA, the submission rates aren’t statistically significant (eg one extra meeting booked would double the submission rates of C and D).

But it’s early days - once there’s been a few months of data we might have some more insights.

Main takeaway: start testing, even the small things - and then forget about it for a few months. Come back and review - if there’s a clear winner, action accordingly.

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💰 Shot 4: HubSpot Sales Feature of the Week

Building Lists Based on Email Subject Lines of emails logged against a contact (Stage 3)


The power of Lists!

We’ve done whole episodes just on using HubSpot lists - they are the building blocks of HubSpot.

And that only scratches the surface.

Here’s another use case that came up recently - our client wanted to build a list of contacts who had received a specific email (sent from another system and BCCed into HubSpot).

It’s quite easy to do using a list that uses Activity criteria:

HubSpot list filters

And then in the Activity properties, use Email activities eg Email Subject:

HubSpot List filters

Once this list is created, you can then make it available in Views (which is where their Sales reps usually spend their time) by using the List Membership filter on a view:

All list filters

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👨‍🔧 Shot 5: HubSpot Service Feature of the Week

Last Activity Date versus Last Modified Date (Stage 3)

This can be a useful distinction to be aware of:

  • Last activity date: the last time a note, chat conversation, call, email, meeting, message, or task was logged for an object (eg deal or ticket). This is updated automatically by HubSpot.
  • Last modified date: the most recent date that any property on a deal was updated. This is updated automatically by HubSpot.

Can be important when triggering workflows - we often trigger workflows based on last activity gaps (eg last activity was more than 14 days ago), but recently have been switching this to use last modified instead - because we found users were actually changing a record (eg moving a pipeline stage) but this wasn’t affecting activity - whereas it does update Modified date.

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🔧 Shot 6: HubSpot Gotcha of the Week

HubSpot Meetings Shortest Schedule Window is 2 Weeks (Stage 3)

An interesting limitation of HubSpot Meetings is that the shortest scheduling window you can configure is 2 weeks (ie This Week and Next Week):

meeting schedule

Why is this important?

Chatting with a new client this week and they described their sales process - and highlighted how important it was in their process to chat with a prospect as soon as possible. If a visitor to their site is interested in booking a meeting they don’t want to give them the option of booking 2 weeks in the future - by then they might have gone with another provider. So they want to limit the available meetings to be within 2 days.

The only way to manage this in HubSpot Meetings would be to use a custom date range and update it every day - ie very tiresome.

For this reason, they’ve switched to using Calendly.

There’s a community thread with people talking about this and how important it is.

Here’s hoping HubSpot updates Meetings to allow a shorter schedule window.

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💡 Shot 7: Insight of the Week

HubSpot Keeps Your Data Intact Even if You Cancel

One thing that is underappreciated about HubSpot is that they actually keep your data if you cancel. Eg if you cancel a Paid subscription and downgrade to Free, your object data (contacts, deals, tickets, etc) is all retained. Which means if you upgrade again later, you can access your historical data again. Note though that this doesn’t necessarily apply to assets (eg web pages).

Thanks HubSpot.

This is in contrast to most other SaaS platforms that will be delete your data when you cancel your account.

The only thing you need to ensure is that you log in to your account every month or so - on free accounts HubSpot will delete dormant accounts.

For no good reason, here’s a picture of some quokkas I generated using Midjourney v5:


(hi res version here)

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🏈 Shot 8: Listener Question of the Week

How to send an email campaign to additional contacts (Stage 3)

This is a common scenario:

  • You’ve set up a regular email and sent it to your list
  • The next day you find another contact you’d like to send it to
  • You can go into the email Details (not Edit) and choose ‘Send to more’ from the Actions menu:

send email to additional contacts


  • only works with regular email types (doesn’t work with Automated or A/B emails)
  • It won’t send to a contact a second time (ie they accidentally deleted the email and want you to send it to them again - this won’t cover that scenario)

See also this quick video:

How to resend an email to more people in HubSpot

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📚 Shot 9: Thought of the Week

Never Use Stock Images Again

The ‘sudden’ rise of AI tools around image (and video) generation means you can confidently plan to remove any need for stock imagery in the coming months.

Here’s some simple examples of imagery we created using Midjourney for use on website pages (layouts, hero shots, people, etc):

Note: in the prompts below make sure you use two '-' in the directives (as opposed to them being combined into a single dash - as many text editors do) eg dash dash v 5

Prompt: a beautiful, organized living room in a modern house --v 5


Prompt: A wide landscape hero shot for a website that shows a professional woman working on a laptop in a modern office, looking confident and happy --v 5


Prompt: double exposure photography of a modern professional office --aspect 21:9 --v 5 --uplight --q 2 --s 750

modern office

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✍️ Shot 10: Quote of the Week

“Tell me and I forget. Teach me and I remember. Involve me and I learn.”

-Benjamin Franklin

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🏋️ Shot 11: Training of the Week

Building a Campaign from Start to Finish in HubSpot

Check out our full walk through of everything to include in a campaign built in HubSpot

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🏋️ Shot 12: Have You Downloaded The HubShots Framework?

HubShots Framework Poster

Download a copy of the HubShots Framework A3 PDF poster (recently updated with colour coding and more).

HubShots Framework

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🧲 Shot 13: Follow Us on the Socials

Connect with HubShots here:

Connect with Ian Jacob on LinkedIn and Craig Bailey on LinkedIn 

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HubShots, the podcast for marketing managers and sales professionals who use HubSpot, hosted by Ian Jacob from Search & Be Found and Craig Bailey from XEN Systems and XEN Solar.

HubShots is produced by Christopher Mottram from Podcastily.

We record using Riverside.fm (<= affiliate link)

Please share this with colleagues - it helps us improve and reach more marketers.


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