Email on Tap, Episode 6: Will Boyd, Senior Email Delivery Consultant, Twilio SendGrid

Anthony Chiulli, 250ok’s director of product marketing, recently visited one of our most valued partners: Twilio SendGrid! He sat down with Will Boyd, senior email delivery consultant at Twilio SendGrid.

Anthony and Will met just as the Twilio SendGrid acquisition finalized, so we get a good look into how these two brands synergize together. Additionally, they delve into Will’s philosophy on email and deliverability, discuss his view of the industry’s future, and even have a little (more) fun at the end. Let’s get to it!

Total Run Time: 11 minutes
0:30 – Will’s feelings about Twilio’s acquisition of SendGrid
1:01 – How SendGrid fits into the Twilio platform
2:09 – Experience working with amazing recognizable brands on email
3:27 – Will’s style and approach in deliverability consulting with marketers
5:19 – New changes in deliverability trends, strategies, and industry changes
8:22 – The genesis behind Will’s legendary spam subject line poem


Listen and subscribe on your favorite platform:




Anthony Chiulli
Hi everyone, and welcome back to another episode of Email On Tap. I’m your host, Anthony Chiulli, and today, I’m really excited to be joined by Will Boyd, from Twilio SendGrid. Will is a senior email delivery consultant. Will, thanks so much for being on the show.

Will Boyd
Thanks for having me, Anthony.

So some exciting news recently, right? Things have been probably pretty thrilling here at the Grid, on the heels of the finalization of the acquisition with Twilio. How are things going?

They’re super exciting. It’s been a crazy time for us here. I may slip up and not say Twilio SendGrid, so I forgive you if you do the same, but everything is really new for us right now. I know the acquisition was announced, I think, late last year, and it just finalized a few weeks ago. And it’s been a fun time for sure. We’re learning a lot about our different companies, and how they’re going to merge together and mesh well, so I know I’m excited about the possibilities, for sure.

It seems like a perfect match. How does SendGrid fit into the Twilio business model and platform?

Well, Twilio, as I’m learning more and more about it, is a super-impressive company with their voice telephony products. SMS, voice video, offering developers the ability to really dig into their API and connect their products directly to their communication substreams. SendGrid has been the same way; we’ve been an API-focused company for a long time. Developers have loved using SendGrid and plugging it right into their products. And having those two streams, with email and the voice, telephony, video products, all-in-one suite where a marketer can actually do all of their communications, and with their customers and their lifecycle marketing in a really exciting way, and have all that data in one place, I think it’s a perfect fit. Both of our companies are really plug-and-play for developers. The sky’s the limit with what people can do with the combined Twilio SendGrid product.

SendGrid averages, I read, nearly 50 billion emails a month, that’s a lot of email. How do you enjoy working with some of the most recognizable brands in the world here at SendGrid?

It’s one of the things I love most about being at SendGrid, that I do get to work with some of these brands. I get to see such a wide variety of email programs, and work with such a wide variety of email marketers. I learn so much from them, it’s one of my favorite things. It’s how they are actually listening to their recipients, and how they are getting to know their clientele, their recipient base, and making their changes based on pleasing them. It’s been really exciting. I get to take little nuggets that I learn from giant brand A, and help giant brand B, or small brand C and everyone in the middle make sense of this kind of weird world that is email, and reputations, and things like that as well. It’s super exciting to be out in the world and hear someone talking about an email campaign that you helped work on, a very large campaign going out about the music you might have listened to last year from one of my clients. I get to hear about that all over Denver, when I’m out having coffee, or having dinner, and that’s been very exciting. So getting to work with those clients is a real boost, a real charge.

That’s awesome. Deliverability is often one of those misunderstood disciplines of email marketing, and tends to not have value until something bad happens for brands. What is your style, or methodology in a way, that you consult with customers on optimizing deliverability or solving for deliverability issues?

A lot of times, the first thing I’m really working with the customer on is to understand email and the factors that impact their results. A lot of times, that’s misunderstood from the very get-go. Marketers want to focus on a lot of infrastructure pieces, and a lot of really technical tips and tricks. Those are all important, and we help them with those, but at the end of the day, it’s how that recipient group is responding to their messages. How those actual human beings are interacting with their brand that truly dictates the ability to get mail to the inbox, to get mail delivered. So, working with marketers to understand that email is not necessarily an advertising channel, in the sense of you buy a TV ad, you have access to whoever is watching that channel; it’s a social channel. There’s that spam button, there’s replies, there’s all kinds of ways a recipient can interact with the messages that are sent. That has a big difference on those marketers’ success. So helping marketers understand that this is a social channel, that this is a relationship channel, is one of my favorite things to do, and watch that a-ha moment when they can see with all of these weird signals. They may be looking at spam traps, they may be looking spam complaint rates, they may be looking at open rates. Helping them draw that picture of how all of those things tell them how their recipients are seeing their mail, and that should help them make decisions on how to make the email more value added, more compelling to their recipients. That’s my favorite part about working with marketers, and one of the harder parts, too.

Yeah, I can imagine. Twilio SendGrid just recently released their 2019 Deliverability Guide earlier this year. What are you saying as far as some of the newer tips or tactics you’re sharing with marketers that marketers can glean from?

That’s a great question. As far as new tips and tricks, I’m not sure I have a lot of, “Do this one thing, do this thing differently.” In our deliverability guide, we, this year, called out a lot of changes in the industry, whether it is the combination of AOL, Yahoo, and Verizon into what was Oath and is now Verizon Media Group, as well as how Microsoft has been working to combine their filtering algorithms, and processes on their side to be more uniform across their different properties, whether it’s or A lot of these changes are pointing to the ways that we’re seeing email be less bifurcated in the industry, and coming together as a more of a holistic piece.

For example, now if you have spam complaint problems at AOL, it can impact your actual results at Yahoo. They may be making different decisions at those different properties, but there is overlap there. You can’t necessarily silo your problems into one specific domain, or one specific issue. It all really does point marketers back to how they are pleasing their human recipients. Those changes, along with things like Gmail making updates to their Promotions tab, always trying to make that more appealing for their users to actually use those Promotions tabs that so many marketers hate and try to get away from, Gmail’s actually trying to make that more usable for a recipient. So that they know where to go to get their promotions, because I look for promotions. I want those discounts, so I use my promotions tabs all the time. So they’re making updates to allow users to actually have markup in their code that allows those deals to be highlighted by Gmail. At the top of the Promotions tab, to make that so much more usable for both recipients and marketers.


So making sense of those changes, I think our deliverability guide calls out a lot of those things really well. And just keeps pointing back to the fact that the hard work of marketing really is making those relationships. We can get you setup with the right infrastructure, we can have all the tools measuring all of the signals we see. But at the end of the day, if you’re not making people happy, you’re not making Google happy, you’re not making Microsoft happy because they want their recipients to be getting email that they want to read, and want to interact with. So those things are a lot of what I really enjoyed about this year’s guide. There’s lots of really good tips and tricks in there about maintaining engagement, and how to look at your opt-in process and things. But it’s all really geared towards making sure that you are providing the best experience for your recipients as possible, because that really is the key to success for getting into the inbox.

Well said, I agree. One of the cool things I thought you did a few years ago was you wrote a poem with subject lines only from spam messages. I recently read that on the blog again referencing back two years ago, when it was published, tell me that story. How did that idea come into play, to draft a poem using subject lines of spam messages?

I live in my spam folder. I am maybe one of the few people on earth that is in their spam folder multiple times a day, looking at all of the mail in there. I believe that if you want to know what wanted mail is, and want to know how to get mail to the inbox, look at what is not working as well. Look at that spam folder. But as I worked through that, just months and months of looking at spam subject lines, I started to go, “Wow, some of these are really interesting just on their own.” Because these were some really hardcore spam subject lines that had really weird language in them. It was clear that it wasn’t necessarily a subject line that was meant to, I don’t know, get me to buy something. It was just a really confusing subject line. So I just started saving the most interesting ones in a file, and I thought, “Well, I can tie these together and pull out real meaning from all of this, and have a nice poem.” So I actually wrote maybe five or six of those from different combinations of spam subject lines. And it seemed to take off, and people really thought it was cool and enjoyed it, and thought it was funny. But I thought it also spoke a lot to how these things have meaning on their own. Subject lines have meaning, and they tell a story. And I thought it was an interesting way to put all of these different subject lines together to tell a whole different story altogether.

Yeah, it was quite entertaining and quite interesting. Will, thank you so much for being a guest on our episode today, and thank you for hosting us here at Twilio SendGrid’s offices downtown.

Well thanks for having me.

Yeah, I appreciate it. We hope you enjoyed this episode. Please be sure to tune in to our next episode of Email On Tap. Thank you.

minute read

Popular stories



BriteVerify email verification ensures that an email address actually exists in real-time


The #1 global data quality tool used by thousands of Salesforce admins


Insights and deliverability guidance from the only all-in-one email marketing solution

GridBuddy Cloud

Transform how you interact with your data through the versatility of grids.

Return Path

World-class deliverability applications to optimize email marketing programs

Trust Assessments

A revolutionary new solution for assessing Salesforce data quality


Validity for Email

Increase inbox placement and maximize subscriber reach with clean and actionable data

Validity for Data Management

Simplify data management with solutions that improve data quality and increase CRM adoption

Validity for Sales Productivity

Give your sales team back hours per day with tools designed to increase productivity and mitigate pipeline risks in real-time