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18 Marketing Automation Specialists Share Their Wins and Fails

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When you specialise in marketing automation, things are bound to go wrong sometimes. Learn the top all-time wins and fails from in-house marketers, consultants, and entrepreneurs.

When you specialise in marketing automation, things are bound to go wrong sometimes. We believe that you should always try to learn from other peoples’ mistakes. That’s why we interviewed consultants, in-house marketers, and entrepreneurs about their top failures with marketing automation.

But…we don’t want to dwell in the negative too, so we asked them their top win too. This way, you can not only learn what to avoid but also learn what to test for yourself.

Keep reading for wins and fails about:

  • Automated email sequences
  • Outreach emails
  • Website behaviour as targeting criteria
  • Technical glitches
  • Language errors
  • And more! 🤓

Check out how easy GoSquared makes it to set up marketing automation based on real user behaviour in your site.

Eunice Brownlee, Marketing Automation Strategist and Founder of Thirty9Collective

behavioural triggers makes an experience personal

Top win – “Share with a friend” automation using website behaviour

“I will always argue that dynamic content with behavioural triggers is going to create the most personal experience for users.”

Back in my higher ed days, we created campaigns that would allow students to send information about the colleges they were looking at both their parents and guidance counsellors. Instead of setting up a simple send-to-a-friend functionality, we used behaviours from the landing page to determine not just what to send, but in what order to send it, and then tailored the messaging to the recipient persona.

The open rates were almost 10 points higher than our other campaigns, and our conversion rates were nearly double that of our standard campaigns.”

Did you know? GoSquared’s Marketing Automation makes it easy to set up automated emails and chat prompts based on user website behaviour.

Top fail – complicated sending criteria

“When building a query, the smallest details matter. Especially when you are looking to exclude a portion of your audience for good reason. For a client, I managed a weekly send to a list of about 140k people with a time-sensitive offer. We discovered that a change in the data file meant that emails had not been triggering for about three weeks. In an attempt to salvage the records that were still viable, we opted to do a manual send to records whose offer had not yet expired and would not be expiring within the next 7 days.

Well, I learned the hard way that using only the criteria that the expiration date “is not within the next 7 days” meant that it was excluding records that were within the 7 day window, but not prior to that 7 days. I ended up sending out almost half a million emails with an expired offer. Changing the criteria to expiration date “is after” and hard-coding the date 7 days out was the audience I was looking for.”

Derek Lenze, Founder of Floating Authority

increase outreach campaigns

Top win – High converting outreach campaign

“I use automated tools for backlinking outreach. In this one outreach campaign, I received about 14 links, including some good high profile websites out of a campaign of about 1000 people which is actually above average for this style of outreach. I was super stoked about this campaign.”

Top fail – Tech glitches

“My biggest win and fail for marketing automation came in the exact same outreach campaign! The outreach tool I was using had a glitch and ended up sending the same email templates to people I had already got links from. While this was not the end of the world, it was super embarrassing to have to come up with a feeble excuse.”

Olga Mykhoparkina, CMO at Better Proposals

conversation rates marketing automation

Top win – success with LinkedIn outreach messages

“Probably the biggest marketing automation win was setting up a drip campaign to send cold outreach messages in LinkedIn, leading them to a product explainer, all the way to a signup form, eventually logging them in our CRM. That way, we immediately knew who came from LinkedIn, what they bought, whether they bought something at all and how good the conversion rate was.”

Top fail – generic CTAs

“As for the biggest fail, it was probably the CTAs we placed on our blog posts which all led to the product signup page. We assumed that everyone who read a blog or two was a potential customer, and the conversion rate was appalling. All the people who clicked on them were at different stages of the buyer journey, and we forced them down the funnel without considering their needs first.”

John Pinedo, Founder of Freedom Bound Business

grow review count with marketing automation

Top win – Strategic requests for customer reviews

“One of the best automation I’ve used was for a local business client that got them hundreds of Google My Business (GMB) reviews during my time working for the tech support company. The automation involved sending an automated email to all customers after 3-days of their service purchase. The email was a customer service feedback email that had a thumbs up and a thumbs down image that would lead to two separate landing pages. The thumbs up lead to a simple page with a headline, some text, and a call-to-action that leads them to the company’s GMB review page. The thumbs down landing page had a pre-made form that would only be directed to customer support email.

This winning automation achieved two things: it grew our client’s review count on GMB and kept any negative reviews from appearing on our client’s GMB.”

Top fail – give your brain a break

“I was once working on an email campaign promoting a tech service plan that was aimed at two audiences: current service plan members and non-service plan members. Each one got a special deal during this campaign, but in one of the automated emails, the current service plan audience was linked to a page that was only meant for the non-service plan audience.

It was a silly mistake. I knew I had to be extra careful, and I had experience handling campaigns like this before, but this was a human mistake while handling a specific set of emails and landing pages for one audience and unique emails and pages for another. It taught me to triple-check instead of double-checking. And to give your brain breaks when setting up an automated campaign.”

Dan Bailey, President of WikiLawn Lawn Care

use segments for better personalisation

Top win – better automated email content

“After noticing the poor results from our automated email campaign, we pivoted quickly, focusing on the quality of subscribers and providing them with content they wanted. Using different lists and segments, we opted for smarter optimisation and only gave the best content at a far reduced rate, further segmenting customers based on their interactions.”

Top fail – audience exhaustion

“Without this fail, we wouldn’t have gotten to where we are now. I learned through various sources that so long as you provide constant content to your prospects, you’ll wear them down and convert them. Just set up a funnel and keep a constant drip-feed going through newsletters. We did this, sending emails daily (yeah… it was bad) and saw a massive drop off in subscribers with few conversions.”

Linda Chester, Founder of The Health Hour

automating marketing strategy

Top win – automating email sequences

“Fortunately, we learned from our mistakes and were able to turn failure into a win by automating most of our email marketing strategy. We now use ActiveCampaign to create automated email sequences and send them out to different email lists. This made it easier for us to tweak our email marketing strategy based on the data we get and bring in more conversions.”

Top fail – only using email blasts and broadcasts

“I run multiple blog sites, and each site has a few different email lists. We use newsletters as an email marketing strategy, and this has been working quite well in getting more people to visit our websites. However, we didn’t always do it that way. A few years ago, we were able to create a good-sized mailing list through a combination of timed pop-up email opt-ins and personalised landing pages. However, we wrote and sent out emails manually to people on that mailing list and did so at least twice a week. It was laborious, time-consuming, and didn’t help with conversions — just a big failure overall.”

Brett Downes, Founder of HAROHelpers

be careful with reminders

Top fail – reminders with hard-to-predict insensitivity

“Our failure was an understandable one, but a bad failure nonetheless. One of our clients is a florist, and we have automatic emails sent out to previous customers whenever a person they know/relative birthday is approaching. This is pulled from their previous purchases at that time. However, as people (rightly) don’t update us or their account when someone passes away, our emails can be an unfortunate and cold reminder that that person is deceased. Most people must have ignored it, but when we had an upset customer email in we immediately apologised and put plans in place to avoid doing this in future.”

Jase Rodley, Founder of Dialed Labs

uptake in submissions

Top win – merging online sales with in-store services

“We worked with a salon in which we created an automatic responder to people signing up to the newsletter where they would be sent an email asking if they would like a complimentary dye pack every 6 months. All they had to do was tick the box, and then they would have an address to send a lock of their hair too for the salon to do a colour match and sample test on.

This is unknown in salons, as most of the customer management and upsells are done in store. This doubled the footfall in a year as most people would come in for a cut within 2-3 months of receiving their first hair dye. There was a 15% uptake of submissions to calling for an appointment.”

Andrew Erickson, Partner at Alaniz Marketing

send to the right group

Top fail – language flub

“This is a major client fail I witnessed…. A software company wanted to send an email to a small list of individuals in a foreign country. The events team set up a workflow to send the email to everyone who was NOT on a small list ( specific country IP and bounced = yes) – which basically meant that they sent this email to everyone in the database by accident – over 150,000 people got an email in a language that they don’t speak. Yikes!”

Jane Kovalkova, CMO at Chanty

marketing automation feels effortless

Top win – leads on autopilot

“The biggest marketing automation win which we accomplished was getting leads from our blog post CTAs to sign up for our demo and automatically added them on our mailing list and our CRM. It felt effortless every time someone new signed up.”

Top fail – Zapier mistake

“The biggest fail was probably when we wanted to create a sheet with all of our customers that use our app AND join our Facebook group. This turned out to be a huge failure because we used Zapier and messed up in one of the last steps. We ended up with a Google Sheet with more than 500 entries of “You have a new Facebook group member”. I still don’t know how exactly this happened, but it’s the reason why we double-check all of our Zaps when we set them up.”

Jared Ebrahimoff, Founder of Lavari Jewelers

solve cart abandonment with marketing automation

Top win – optimising the abandoned cart sequence

“Our team’s biggest win was optimising our abandoned cart email sequence. Although we had an existing email sequence, any reader reading it can tell how rushed it was. It wasn’t optimised for conversions. Luckily, we did a complete audit of our current marketing campaigns to optimise our metrics and found this mistake.

“It paid off the copywriter’s fees with more to spare during the first month of its release.”

We hired a seasoned copywriter to write the sequence for us to ensure a positive result. The outcome was miraculous, and the sales from the email comprised 15 percent of the revenue at its peak performance. It paid off the copywriter’s fees with more to spare during the first month of its release.”

Top fail – making assumptions without split-testing

“Split-testing exists for a reason—to help marketers choose between advertisements. However, some marketers would argue that some results are inevitable even without doing a split-test. Our team was guilty of this, and we were dead wrong.

Every Valentine’s Day, we hold promotions geared towards men and advertise products they can give their significant others. However, we saw a Valentine’s Day ad that advocates self-love for single women. Out of curiosity, we ran an advertisement geared towards women and got the shock of our lives. It turns out that single women were an even better audience for us.”

Nadia Milani, Marketing Director for TeraGo

increase sales and click through rate

Top win – automated nurture campaign

“We launched an automated nurture campaign to drive engagement and purchase on e-comm site. The goal was to increase sales, specifically for SOHO and SMB customers. We built automated nurture campaigns to onboard the customer, incentivise for the first purchase and then second purchase. We were able to increase sales by 15% in the first 3 months of launching the program, CTR increased from 2.7% to 9%, and open rates increased from 22% to 28%.”

Top fail – database deletion

“We once ran an erroneous campaign in Marketo that deleted our database! A user accidentally checked the “delete contacts in CRM” flag. All contacts were also deleted in Marketo and Salesforce. Queue sales team panic. We learned that back-up is really important i.e. opt-out data. We were able to recover 99% of the data. Luckily, we had downloaded a file with opt-out data prior to this boo boo.”

Quincy Smith, Founder of ESL Authority

marketing automation

Top win – Website behaviour triggers

The biggest win we’ve had is using website interactions to trigger timely and relevant emails. For example, if we see a user browsing 2 or more jobs in a specific country, we will send them an email letting them know we can help them find a job in that country. It’s worked really well, and we’ve landed a lot of clients like this. It’s very much a ‘right place at the right time’ kind of success.”

Did you know? GoSquared’s Marketing Automation makes it easy to set up automated emails and chat prompts based on user website behaviour.

Top fail – tactic not worth the effort

“I had a timely and costly fail with a previous consulting client – their software integrates with a few big platforms so we spent the time synching Built With + Hubspot so they could send campaigns based on what software their leads were using. In the end it was far too granular a message, and the leads responded more to general pain points instead of messaging related to how we could help a specific piece of their software stack.”

Mark Webster, Co-founder of Authority Hacker

drive sales with marketing automation

Top fail – evergreen and realistic limited time offers

“Our biggest win is currently still active on our site. We have a typical opt-in pop-up; however, instead of asking for an email, this leads them to join our free training webinar. We actually ask them to book a slot for one of our pre-recorded webinars which is packed full of information on website building.

At the end of the webinar, they are invited to check out our course with a special discount as a thank you for watching the webinar. However, this is not an evergreen discount and it only lasts 7 days. It’s tied to their email and IP so they cannot simply sign up again.

This is fantastic because it allows us to create evergreen scarcity without sacrificing our integrity when we say “Limited time”. The offer genuinely is limited time and helps drive sales as well!”

Top fail – website QA issue

“Perhaps one of our biggest fails involved a fairly regular automation funnel. We had a limited time launch and a sequence of emails going out to drum up interest.

When the cart went live, however, we realised that due to compatibility issues, a huge portion of our audience couldn’t actually purchase the course we were selling as the sales page did not work on iOS Safari browsers.

Since then, we’ve always made a point of running a compatibility check before launch!”

Eden Chai, Co-founder of Generation Marketing

marketing automation turn leads into clients

Top win – freebies that bring in sales calls

“I’m the co-founder and account strategist at an apartment marketing agency. The best automation campaign that I ever set up was driving traffic to our free downloadable resources to generate leads. After a lead would insert their contact information, we set up an email sequence to schedule a call with one of our account executives. The landing pages converted at 11%, and we were able to turn every 1 out of 7 leads into a client.”

Top fail – wrong webinar time

“One of my biggest marketing automation blunders was setting up a webinar 1 year ago, where I would teach smaller unit landlords how to utilise digital marketing to get more tenants. I got the time zone wrong because it was right after daylight savings time change, and I logged on an entire hour late. The registrants were so frustrated with the webinar not starting, we couldn’t generate one positive response from the webinar follow-ups.”

Meg Marris, Founder of K9 of Mine

customised marketing automation

Top win – Relevant and targeted automation sequences

“One of my best wins has been taking the time to set up customised automation sequences for various audiences. For example, those who visit a page about puppy training receive a different opt-in form and are put into a different group specifically for “puppy owners”. They then get a 5-7 custom email automation sequence offering puppy training tips, before getting added to my larger, more general automation sequence about dog training.

Starting with a more customised, tailored automation sequence has DOUBLED my open rates and click-through rates! Plus, it allows me to market future email campaigns more specifically to certain groups, as I can tailor the language to focus on “puppies” for my puppy group, resulting in more perceived relevance.”

Top fail – upgrade emergency

“I once set up a very time-sensitive automation campaign that did not end up being sent because I was over my subscriber limit. Even more frustrating, I had paid to upgrade my subscribers, but the software I was using would still not complete the upgrade process until I manually confirmed the upgrade with them via their support chat.

This was VERY frustrating since I missed out on sending a very timely, important email!

The lesson – always make sure you are 100% set to send and under your subscriber limit before launching a big email campaign!”

Andrus Purde, CEO of Outfunnel

create personal pitches based on user behaviour

Top win – personal pitches based on user behaviour

“We use web visitor behaviour and segment them to lists automatically. Visitor behaviour data syncs with CRMs like Pipedrive or Copper. Specific behaviours trigger the assortment of users to different mailing lists.

The more interest they have, the more pages they visit, the more interactions they have with our product leads them further down the line. Our sales team can prioritise calls based on which list leads are on, and create personal pitches based on user behaviour.”

Reuben Yonatan, Founder and CEO of GetVoIP

marketing automation subscribers

Top win – prioritising email marketing

“My biggest marketing automation win was integrating email marketing software into our marketing strategy. The goal was to grow our email list, which would, in turn, increase our revenue because affiliate marketing is our company’s main source of revenue. Fast forward four years later, and we now have an email list of over 100,000 subscribers, and the number keeps growing.”

Top fail – tech overload

“My marketing automation fail? Too much tech! As a marketer, it is tempting to keep purchasing the latest marketing technology. Unfortunately, that it’s new and shiny does not necessarily mean it will work for you… Once I learned that harsh lesson, I now only purchase martech after careful consideration. It must be tech that I am sure will be useful.”

It’s true that some mistakes we have to make for ourselves, but hopefully, after reading these top wins and fails from marketing automation specialists, you’ll learn from some of their triumphs and mistakes too.

Sign up for a free trial of GoSquared’s Marketing Automation

Written by
Dayana is a B2B SaaS copywriter and content marketer who lives in Northern California. She loves messaging and storytelling alike.

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