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The Fantasy Football Commissioner’s Guide to Easy, Effective Emails

Fantasy football commissioners guide to effective emails

Sending effective fantasy football email messages is a part of your sworn, sacred duty as commissioner … even if the fantasy apps handle a lot of the heavy lifting these days when it comes to communication.

Yahoo, ESPN, CBS Sports, and the other fantasy platforms send reminders when people haven’t set their lineups. They take care of scoring updates. They email trade proposals (and rejections, at least for every trade I propose).

But as league commissioner, there’s a set of other crucial emails you need to send before, during, and after the season.

After all, Yahoo may be able to tell you how many fantasy points Amari Cooper had on Sunday… but they can’t tell you whether Jeff is going to be available to hold your draft in Vegas on August 21st. (It’s always someone named Jeff holding things up. In every fantasy league now and throughout history.)

In this guide we’ll cover four emails fantasy football (and fantasy baseball, basketball, hockey, golf, pro wrestling, Bachelorette, and everything else) commissioners need to send.

And we’ll cover how to send these mass emails in GMass for easy personalization, follow-ups, and more — without ever having to leave Gmail.

Fantasy Football Email for Commissioners: Table of Contents

Getting Set Up with GMass to Send Personalized Mass Emails in Gmail

GMass is a Chrome extension that transforms your Gmail (or Google Workspace) account into a mass email platform. With GMass you can send personalized, individual emails to large or small groups without having to use BCC or an external email service like Mailchimp.

It’s free to get started with GMass — you’ll be able to use all the features of the platform and you can send 50 emails a day during your trial.

So before we jump into this guide, there are two things you should take care of…

Download the GMass Chrome extension and install it

Install GMass from the Chrome Web Store

You can grab GMass from the Chrome Web Store.

If you want a brief introduction to GMass, what it can do, and how it slides right into Gmail, you can take a swing through the GMass quickstart guide.

You could even do a test run of GMass by sending a league-wide announcement.

Get everyone from your league into a Google Sheet

Everyone in your league in a Google Sheet

You’ll need everyone’s email in your Google Sheet at a minimum. But as you can see from my example, I also included first names, last names, team names, and team ownership role. Make sure to include yourself as well — that’s key for testing purposes.

As a commissioner, you may have to account for teams with multiple owners. I set up my spreadsheet here with every league participant on their own row, even if they co-own a team. In each case I’ve designated who the primary owner is, which will come up in situations like voting on league rules and payments.

And yes, I’m doing an eight-team league for my examples. If it was good enough for The League it’s good enough for me.

Now on to the emails…

Emails for Planning and Scheduling the Draft

Coordinating on a time when everyone is available to draft is more challenging than it should be. Especially if you’re doing an in-person draft. And double especially if you’re doing a destination draft.

But as commissioner, it’s your job to make sure no one ends up needing to use auto-draft… and then winds up with five kickers and three defenses.

In this example we’ll go through setting up a scheduling poll with Google Forms, sending it out with GMass, then automatically following up with people who haven’t put in their available dates.

Setting up your scheduling poll on Google Forms

Create a new poll on Google Forms to get started. Use the “Multiple choice grid” option to input your various time options.

Create a poll on Google Forms

In the Settings section of Google Forms, choose to collect email addresses.

Collect emails in the Google Forms settings

Then in the Responses section of Google Forms, click the Google Sheets icon to collect responses. You can choose either to Create a new spreadsheet or Select existing spreadsheet. (If you select your league spreadsheet, Google will add responses in a new sheet tab. It’s a good way to keep everything organized.)

Create a spreadsheet for answers

Next, check your survey to make sure everything looks right.

Check your forms survey

Then click the Send button in Google Forms.

We won’t use the Google Forms email option because we want to be able to send follow-ups to people who don’t respond. So we’ll grab the link to the survey instead.

Grab the survey link

Set up the email

Go to Gmail and open a new compose window.

Click into the Recipients field, then click the GMass icon that appears on the right.

Click the GMass icon

Choose to add recipients “From a Google Sheet.”

Add recipients from a Google Sheet

Choose your Google Sheet from the dropdown, and pick the correct sheet (“Form Responses 1” would be the incorrect sheet. Google Forms may have added that to this file.)

In the optional settings, choose to Update Sheet with reporting data.

Google Sheet connection settings

You can now write your email like any normal Gmail message.

Compose your fantasy football commissioner emails

Adding personalization

We’ll use mail merge personalization to add people’s names to the subject line and the email message to try to (1) better get their attention and (2) make it clear we’re specifically talking to them.

GMass brings mail merge to Gmail — and it’s all via the columns in your Google Sheet. When you type a left curly brace { , your column names will appear… and you can use those for your mail merge.

Merge options appear

I’ll use those merge fields to add the owner’s first name to the subject and message. I also added a mention of their team name to put a little fear into them.

Using the merge fields in the email

Set up automated follow-ups

We want to use automated follow-ups for people who don’t vote in the scheduling survey.

Click on the little arrow next to the red GMass button in the compose window to bring up the campaign settings for this email.

Click into the section that says Auto Follow-up.

Check the box under Stage 1. Set it If No Click after 2 days. Then enter your message. (As you can see, I can use mail merge here as well.)

Set up your first auto follow-up

A note on “No Click” as our determining factor

Why “No Click”? That means this auto follow-up will go out unless the person has clicked on the link in the prior email.

We’re going to assume if someone clicks on the survey link, they’ll vote on dates. If they don’t click on the survey, they won’t.

This does not, however, account for people who click the survey but don’t vote. We could create a more complicated workaround here to account for that situation (if you want to create it on your own, it involves GMass suppression lists). But rather than going through that, we’ll assume clicks are an almost-exact proxy for voting.

Setting up even more follow-ups

You can set up a few more auto follow-ups if you’d like; I recommend sending one every few days. In my example, I’ve set up four auto follow-ups. I assume by that point everyone will be tired of my emails and will vote. And that’s what this is all about: Wearing down people to the point where their laziness is now the less appealing life choice.

Even more auto follow-ups about scheduling times

Testing the email and survey, then sending the email

Once your email is all set, it’s good to test it by sending it to yourself.

You can see how the first message and all the follow-ups will look by clicking the arrow next to Send Test at the top of the GMass settings box.

The Send Test arrow

In the menu that appears, check the box next to “Send all stages.”

Send all stages

Then click the Send Test button. You should get the entire email sequence in your inbox.

A test of the entire scheduling sequence

Everything looks good to me. The mail merge fields all filled in properly and the auto follow-ups look how they’re supposed to.

For testing purposes, I also clicked through the link and took the survey — I want to see what the players will experience.

All looks good there as well and Google Forms correctly recorded my responses.

Google Forms first results

So since everything is set, I can send the first email by clicking the red GMass button. (And then, all follow-ups will go out automatically to people who don’t click.)

Send the scheduling email

Voting on New Rules

The next email we’ll cover is one to alert owners about a vote on new rules.

Like the scheduling email, this one involves a poll. But unlike the scheduling one, here we want only one vote per team. (After all, if some teams have two owners, they shouldn’t have double the voting power.)

So in this situation, we’ll use a filter to ensure it’s one vote per team.

Create your voting poll in Google Forms

Create your voting form in Google Forms using the Multiple choice grid.

Create your voting poll in Google Forms

In the Settings, choose to collect email addresses and limit to one response.

Collect emails and limit voting

Then click the Send button, and copy the link to your survey to include in your emails.

Connect your Google Sheet to GMass filtering out teams with multiple owners

Now that the voting form is built, your next step is to set up a campaign.

As I mentioned earlier, we want to ensure each team only gets one vote. So we’ll use GMass filtering to remove secondary owners as we connect our sheet.

Create a campaign and click on the GMass icon in the To field to connect to your spreadsheet.

Choose your Google Sheet from the dropdown.

Expand the Optional Settings to use the Filter Rows feature.

In my league spreadsheet, I gave each person a “Role”: Sole for sole owners, Primary for primary owners of co-owned teams, and Secondary for secondary owners of co-owned teams.

We only want this email to go out to the Sole and Primary owners.

So in the Filter Rows section, I’ll add the filter Role != Secondary. (For those unfamiliar, != means “does not equal.”)

Filtering rows

Now when I click the “Connect to Spreadsheet” button, GMass will only pull in the emails of people in the Sole or Primary ownership roles.

Compose your voting email

You can compose your voting email now. Since we’re doing one vote per team, I’m addressing people by their team name here mostly, using the corresponding mail merge field.

Compose fantasy football email

Use conditional content to give a special message to teams with co-owners

I’m going to use GMass’s conditional content to add a special message to teams with co-owners — letting them know they need to discuss before voting.

So I’ll add this at the end of the P.S.: {{If Role=“Primary” Then}}So {OwnerFirst}, make sure you talk with everyone in the {TeamName} ownership group before you vote! They didn’t get this email, only you did as the designated primary owner.{{End If}}

Now people who have a secondary owner or owners will get this extra, personalized reminder in the email.

A conditional content addendum

Set up auto follow-ups

We’ll set up auto follow-ups for this email — which will go out automatically to people who don’t click the voting link.

Click the arrow next to the GMass button to bring up the GMass settings for the campaign.

Go into the Auto Follow-up section and check the box under Stage 1. Then set up your first follow-up to go out if there’s No Click after 2 days.

The first auto follow-up to the rules email

You can set up more stages in your auto follow-up sequence from there. In this example, I set up two more. Also notice I used the “set time” feature in the last one to really give people the feeling of a ticking clock.

The auto follow-up rules series

Test the sequence and poll, then send the email

Send yourself a test of the sequence by clicking the arrow next to the purple Send Test button in the GMass settings box, then checking the box next to “Send all stages.” Click the Send Test button, and you should receive the entire sequence in your inbox.

A test of the full rules voting sequence

Everything looks right to me. Since I’m a sole owner of my team, I didn’t get the special message that goes out to someone with a co-owner.

If you want to test how the emails to everyone will look (not just your own) to make sure that conditional content works right, you can go to the GMass settings box for the campaign and choose to “Create Drafts” in the Action section.

Create drafts of the emails

Then, when you press the GMass button to send the campaign, all of the emails will go to your Gmail Drafts folder. You can check them out, make sure they all look right — then click a link in an email you’ll get from GMass to send those drafts out to your owners.

Test the voting

You can test out your Google Form by clicking through your link and voting.

Test the voting

Everything worked correct and I can see my voting results are now showing up.

The results of my voting test

Sending the email

Since everything looks right, you can hit the red GMass button to send your campaign. The follow-ups will go out as scheduled to people who don’t click.

Reaching Out to Potential New League Members

One of the main ways people use GMass? As a cold email tool. While the emails you’re sending to potential new members aren’t necessarily cold emails — a lot of the standard cold email strategies still apply.

You need to catch their eye with a subject line, send them a personalized message and pitch, and send automated follow-ups until they reply.

Setting up your Google Sheet of potential new league members

Put your potential new members into a Google Sheet before you send this campaign. In my sheet, I included columns for email, first name, and last name. I also included a column where I typed up a one-sentence explanation of why they’re receiving this email. (And I included myself as the first row, for testing purposes.)

A spreadsheet of potential new league members

Once your sheet is ready, connect it to a new GMass campaign. (Like before, open a Gmail compose window. Click into the Recipients field, then click the GMass icon that appears. Connect to your Google Sheet.)

Connect the prospects sheet

Compose your email

Much like a standard cold email, you need to accomplish a lot with this email using limited words:

  • Catch the prospect’s eye in their inbox to get them to open the email.
  • Make it clear this is a personalized pitch.
  • Get across details that close the deal.
  • Get them to take an action (usually to send a reply).

Here’s the email I put together to achieve all that:

My email to prospective new fantasy members

I personalized the email by adding their first name in the subject and the message. I also included that “How” field to let them know the reason they’re getting this email. That will make these emails feel especially personalized.

If I were writing a cold email, I probably wouldn’t include such a long paragraph of details. But for this fantasy league, I wanted to hit the key points to pique the person’s interest. And I figured they’d read a little more, since this isn’t a purely cold email (it’s more of a lukewarm email).

ended the email with a call-to-action, telling the person to reply if they’re interested. And I added the line about only adding two people to increase the sense of urgency via scarcity — which should spur a faster reply. Plus I threw the joke in there because this is fantasy football, not life or death.

Setting the preview text

There’s one more tactic I’m going to use to catch a prospect’s eye in the inbox, and that’s the preview textPreview text is the text that appears next to or under the subject line in someone’s inbox.

In this case, I’m going to put my {How} field into the preview text. That way these prospects will see their friend’s name in the inbox and be more likely to open this email.

To set the preview text, click the arrow next to the GMass button to pull up the GMass settings. Go into the Advanced section.

You can type anything into the preview text — including any merge tags. In this case, I used the {How} merge tag.

Setting preview text for the email

Setting up auto follow-ups

We don’t want to bombard these prospects with emails — but we do want to give them every chance to respond. So I’m going to use a sequence of two follow-ups.

I’ll send the first after one day and the next four days after that.

To set the auto follow-ups, go into the GMass settings. Open the Auto Follow-ups section, and set the first reply to go out If No Reply after 1 days. Set the second message If No Reply after 4 days.

Auto follow-ups to prospective new members

Testing the sequence, then sending

Test the sequence by sending it to yourself. Click the arrow next to the purple Send Test button in the GMass settings and choose to Send all stages. Then hit the Send Test button.

The first thing I see in my inbox is the preview text worked right. That’s my personalized {How} message next to the subject line.

Preview text in the inbox

When I open the sequence, everything looks right inside as well. All the merge tags are filled in as expected.

The sequence test for new members

Since all looks good, I can send the first email in the campaign by clicking the red GMass button in the Gmail compose window. And the follow-ups will go out to people who don’t reply.

Canceling the follow-ups if you get too many replies

Let’s say this email works almost too well — and four people respond the first day saying they want to join.

You don’t want to grow the league much more than that, so you need to cancel the auto follow-ups to the other people on the list.

The quickest way to cancel your auto follow-ups is to find the draft and cancel from there.

You can find it in your Drafts folder Gmail.

Open the draft, go into the GMass settings, and click the button to cancel follow-ups.

Cancel emails as needed

Automated Emails to Get Everyone to Pay Up

I saved the biggest fantasy commissioner challenge for the end: Hounding people to pay.

Rather than using auto follow-ups, we’re going to use a repeating campaign here to keep nudging people who haven’t paid their dues.

Adding payment columns to your spreadsheet

I’m going to add some columns to my Google Sheet to use in my emails to people when their league fees are late.

My spreadsheet only includes the primary owners of each team. I have columns for email, first name, last name, team name, paid, days overdue, and number of people unpaid. (Yes, each row will have an identical field for how many other people in the league haven’t paid. That will come up in the emails we send later.)

Adding payment-related columns to the members sheet

Here’s my Google Sheets formula for the DaysOverdue column. If the PAID column is empty, I use the DATEDIF Google Sheets function to calculate the difference between payment due dates and today. So the formula in the first row is =IF($E2 = "",(DATEDIF("7/15/22", TODAY(), "D")),""). You’d swap in your payment due date where I put 7/15/22.

For the TotalPaid column, I’m adding up the non-blanks in the paid column. The formula in every row is =COUNTIF($E$2:$E$9,""). You’ll see how I use this info in my email shortly.

The next step is to connect this sheet to GMass. We’re going to use filtering to remove people who’ve paid.

As usual, open a Gmail compose window. Click into the Recipients field, then click the GMass icon.

In the optional settings, we need to filter out everyone who’s paid. So we’ll add the filter PAID =. That means we’ll only send this email to people whose spreadsheet rows have nothing in the PAID column.

Filter out people who have paid

Compose your email, using mail merge to let people know how late their payments are

Compose your email. I’m going to use mail merge options to add the amount of days people’s payments are overdue — and how many other people in the league have paid.

The message to get people to pay

Turn into a repeating campaign

Now we’re going to turn this into a repeating campaign. With a repeating campaign, this email will keep going out to each person with an overdue bill — with updated days overdue and total people paid — until they pay.

Open the campaign settings by clicking the arrow next to the GMass button.

Go into the Schedule section. Then check the box next to Repeat. Set the campaign so it repeats every 3 Day to all rows.

Turn the fantasy football email into a recurring campaign

Here’s what that means. Every three days, GMass will look at every row in your Google Sheet. It will take everyone who hasn’t paid (whose PAID column is empty) and send them this email. Because we set up a filter when we connected the sheet, GMass will always screen out any people who have paid (even if they pay after this campaign goes live).

You won’t have to do any of this manually. Set this up once, and GMass will keep on sending the emails.

The only thing you have to do by hand is mark in your spreadsheet after someone pays. (Though if you want to get extra fancy, you could use Zapier to automate that as well.)

Test the campaign, then set it live

You can test the campaign by hitting the Send Test button in the GMass settings.

And here’s my test email, in all its shaming glory.

The test email for late payments

Once everything is ready, set the campaign live by hitting the red GMass button. And now, the campaign will repeat every three days until everyone has an “X” in the PAID column of your Google Sheet.

Fantasy Football Commissioner Emails: Next Steps

We hope this guide makes your life as a commissioner easier — and your major fantasy football commissioner emails a whole lot better. At the very least, this guide should help make things more automated. I say: Let the robots track down late payments — you have other stuff to focus on.

And beyond your fantasy football life, we hope this helps you see the potential for all the ways you can use GMass in your professional and personal life.

GMass has more than 300,000 users putting it to work in tons of different ways:

If you haven’t done this yet, download GMass for free from the Chrome Web Store. You’ll be up and running in a matter of minutes. You can send 50 emails a day for free during your trial.

And good luck with your fantasy league this year. May your best players not be last-second scratches and may your goal line touchdowns stay unvultured now and for years to come.

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