• Charles Edge

Bootstrapping And Need Inspiration To Get Started With Email Marketing? Here Goes!

Email marketing is one of the top ways for software company to maintain connections with customers and nurture those relationships. In fact, sometimes it seems like every time I turn on the radio, there's an ad for an email marketing automation tool like Constant Contact, Mailchimp, iContact and even Salesforce. And they can make it easy for small and mid-size businesses to automate beautiful emails and build logic around that messaging. And larger organizations can find a lot of success with more enterprise-class solutions like Marketo, Adobe Marketing Cloud and Eloqua.

The ads make it sound like these campaigns write themselves. But they don't and there’s a lot of art in communicating with customers authentically, effectively, and in a way that resonates with the journey they’ll have with our products.


Email marketing is a delicate business. On the one hand, you don't want to be an evil spammer. Nor do you want the law suits that could come from doing so. And on the other hand, email automation is one of the only ways you can communicate with a lot of customers with any kind of frequency.


Along our journeys to align email marketing with a great customer experience, we’ve seen a lot of really great techniques, and some pretty bad ones. So here are some lessons we learned along the way:


Be as customized as the platform allows.


Be timely. Did a customer start a trial? Get them some tips for how to use the type of product they signed up for. Is it budget season? Help them prioritize. Build systems before having people opt into lists, so too much time doesn’t expire and they forget the name.


Be authentic. We all have a voice. The humans and the products. Give the product a voice or let sellers create their own custom campaigns. Be authentic with that voice and try to establish a great relationship with customers with consistent messaging the reinforces a kind and helpful stream of content.

Map the customer journey. A map of how a customer interacts with a product has a lot of great uses. One is that at each stage along the journey with a product, the customer can receive meaningful and tailored content for where they actually are. If they haven’t yet become a customer, if they’re evaluating the product, if they’re in a trial. All of these can be used as attributes to help get the appropriate content out at the appropriate time.

Don’t send any emails that don’t provide value. Each person will perceive value in their own way. Keep in mind that we always want to be worthwhile in our communications. To some that will mean learning more about the product but for others, the human getting the email might not ever become a customer but could still have a positive impression of a brand based on those communications we send them.


Choose an email automation tool that fits the size of the marketing team. This might be a prosumer product early. Keep in mind that robust, enterprise class products need a staff person at the reins. Organizations that can't afford someone in that position should self-identify with an appropriately sized product. And that might be whatever is built into the Customer Relationship Management solution, like Salesforce or Hubspot.

Use a third party tool instead of Outlook. You know that unsubscribe button? It doesn’t usually come for free. We don’t want to violate laws like the European Union's General Data Protection Regulation (GDPR). We also don’t want to hit rate limiting controls like those in place at a lot of mail hosts and Internet Service Providers (ISPs).


Protect personally identifiable information. Those email addresses and other contact details are hard won. And no one wants to be the cause of leaking that confidential data. Use strong passwords with multi-factor authentication with the email marketing platform and never sell customer information unless there’s a privacy policy that explicitly states it’s ok to do so (and even then it's still probably a bad idea).


Don't take things too seriously. We’re all inundated with a lot of emails. Boring, dry emails get old fast and people will almost invariably unsubscribe (except your competitors). We should have permission to be ourselves and conversational. We should be free to poke fun at ourselves every now and then. It resonates and makes each organization a little more human. And it makes our jobs a little more fun.


Automate syncing contacts with the CRM. This isn’t always necessary as many a Customer Relationship Management (CRM) has leaned into features that allow for managing email communications. But syncing those events (opens, clicks, replies) gives us valuable insight into how the content in our messaging gets interacted with by those receiving it. Sure, syncing this data can be labor intensive and cause technical misfires that end up adding people who have unsubscribed back in, or sending people duplicate emails but we can deal with those issues as they arise and go above and beyond to make things right when it happens.


Use email automation to cross-sell goods and services. One of the most important aspects of email automation is to convert leads to customers. Customer retention is critical as well. But we can also sell them other items in our portfolios. We don’t want to be too too salesy or constantly bombarding customers with offers for more stuff. But dripping content out that is fresh and pertinent to customers can often come with overlap between adjacent products.

Use email automation to improve products. Don't use email just to hawk products. Send thought leadership content such as an interesting industry reports to stay engaged with customers. And use existing customers and even leads that haven’t yet converted to help improve products as well.


Have a call to action. Each message we send a customer should provide more pathways for the customer to interact with us. This might be a “Read more” button, a “Try free” option, or a link to see similar content. The key is to use each piece of content we provide to drive engagement to another. Provided the content is timely, relevant, and authentic, we should be able to stay engaged with customers by providing podcasts, blog articles, templates, and other content that keeps them on the journey we want to help them along.

Pay attention to when people unsubscribe. That is a pretty simple message usually, stop doing what caused them to want to disengage with you. If people are clicking through content, we’re probably doing a good job, if not, maybe not. But if they click unsubscribe we’re definitely doing a bad job.

Don’t forget about social media. A lot of email gets disregarded but social networks like LinkedIn are great for making new contacts and nurturing them. A number of messaging tools and CRMs now provide customers with the option to integrate social media. This provides both a free and paid approach to managing messages sent to leads at scale and provides insights into how potential customers are engaging with content.

Ultimately, email marketing is one of the most powerful tools we have in our arsenal to convert leads to customers. Once we have a solid messaging solution in place, we can start to keep those conversations going and have them in ways we never could have before this era. Picking a tool isn’t permanent.


Start small and work your way to a more complex and rewarding experience. Also don’t feel like we have to message everyone in our database at once. Experiment around and find the right ways to communicate with customers. But keep the conversation honest and authentic. That will win the hearts and minds more than anything else!

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