Hey, boo 👋

Just wanted to pop by with an upsell strategy you can steal—and to say I’m proud of you for making it through the first quarter of 2025 ☺️ 

Before I dive into breaking down the upsell stuff, I want to mention that, while you or your team’s focus my be different this year, you can still drive upsell shmoney.

In fact, I’d argue it’s some of the easiest revenue to drive if you’re willing to put just a few extra activities in place to influence your company’s ARR.

But hey, it’s not all about your boss 😉 

Influencing revenue gets you a seat at the table…and, more importantly, helps you build a case for a promotion and a raise. Why shouldn’t your ARR increase when your CEO’s does?? 🤔 

Anywhooooo, enough chit chat—let’s get into it 👇

Start low, go slow

Back in the day, I spent a spell working in Canada’s cannabis industry.

(Yes, it was the high point of my career—no pun intended, lol)

No: I didn’t get free weed 😌 

But there was always one saying that stuck with me from those good ol’ days: “Start low, go slow”.

Turns out, that very sage advice applies not only to edibles, but also upsell.

The premise is to do the exact opposite of what your boss probably wants you to do:

• No spray-and-pray tactics that try to sell to everyone and their uncle

• Instead, intentional upsell programs that focus on customers who will actually benefit from being upsold or cross-sold

Take my upsell approach, for example 👇️ 

My aim with upsell this year is to simply focus on a handful of target customer accounts that will actually benefit from additional platform usage or use cases. That means doing a few small activities that allow me to crawl > walk > run with upsell.

How can you start small?

Here’s the approach I took to start off slow and avoid overwhelming both myself and our team with upsell!

• Decide how much upsell revenue you want to influence this year

  • Example: I chose $300k based on historical upsell revenue data from 2024

    • You can choose your influence number or KPI based on similar data

    • This number is realistic for me, based on past data, as a team of one

• Talk to Sales about their current accounts

  • Example: I asked each of our AEs to provide me with 1-2 customer accounts they feel would benefit from upsell or cross-sell, plus rational as to why they’re recommending the accounts

  • I then narrowed down the list based on contract status, platform usage, and other lifecycle data

    • You can (and def should!) do the same, and see if Sales is willing to partner with you on identifying target accounts

• Map out the ACV of your target accounts

  • Example: I looked at the average ACV of the 12 target accounts I chose, and mapped out the increase in value of those accounts if each was upsold or cross-sold

    • You can easily do the same by either looking at Opportunities or deal records in your CRM—or straight up asking Sales or your Ops folks for each account 😄 

• Choose 2-3 upsell activities you can realistically launch

  • Example: I’m going all-in on in-app this year, as well as testing curated webinars for target accounts; email will take a bit of a back seat!

    • The idea here is to choose activities you can realistically push live that aren’t going to have you biting off more than you can chew

    • Remember: when it comes to upsell, sometimes less really is more.

Once you’ve landed on the target accounts you want to focus on, you can start doing research 🤓 

When performing account research, here’s what I look for 👀 

If it looks like a lot, don’t get too scared at this stage! You can find most of the answers to these questions, or the data you need, in places like:

• Salesforce or Hubspot records

• User profiles in your platform or CRM

• From CS and Sales, if you have other data gaps

I pull all of this info myself, and I’m not a MOps or Biz Ops pro, believe me 😂 

Pull what info or data you can—some is better than none at this stage.

Next, plan out your core activities

Deciding on the activities you’ll launch really starts with mapping gaps to opportunities.

For example, here at Copy.ai, one of the biggest gaps we had was in-app support, and customer nurture.

Knowing this, I was able to map those gaps to key opportunities for how we can help existing customers get the most out of our platform, which will influence upsell/cross-sell.

At the same time, I wanted to start testing activities the company hadn’t ever really tested before—such as lifecycle abm campaigns—with my target accounts 👀 

Here’s a breakdown of my rationale for the activities you see above 👇️ 

First: start with 1:few

I started by identifying the number of target accounts from existing customer accounts, with the intention of:

• Launching hyper-targeted nurtures (relationship building with the account) and championship of top builders within those accounts

• Gifting (top builders and their teams, at milestones)

• Testing technical events (like workshops centered around technical education, office hours)

• Upsell of accounts ahead of activities like renewals

Second: test 1:many activities

The next step is to focus on users in prospective customer accounts (which we tier out), then move those prospects from 1:many to 1:few based on activity and customer status. That looks like:

• General, topical messaging and education to drive platform use

• Nurture potential top builders

• Build rapport for future upsell

• Gifting (swag only)

• Events (centered around evangelism; group demos)

From an ABM perspective, my plan is:

• Run and test 1:few LinkedIn ABM ad campaigns that target 8 Lifecycle target accounts

• ABM campaigns will be paired with 1:1 outreach

• Target accounts are existing customer companies where we see upsell/cross-sell opportunities (based on data, research, customer discussions)

Now, I’m not saying this will work for your company in the same way it’ll work here 😋 

But, it’s a good starting point to think through which activities make sense for your company, your goals, and what’s doable with your capacity.

(You also don’t have to launch everything at once!)

Then, consider how you’ll measure success

Your boss may disagree, but the measure of success for upsell and cross-sell isn’t just money 🤯 

I measure success in the following order:

1. Customer success

2. Customer retention

3. Company revenue

Lemme give you an example 😆 

Customer success may translate into things like…

In other words, customers feel enabled and empowered to leverage our platform to drive success in their own roles.

Revenue driven from upsell or cross-sell will be the result of your team putting your customers first, and giving a s**t that they can genuinely benefit from upsell or cross-sell.

This means carefully thinking about:

• Why you’re upselling or cross-selling these specific accounts, and why now

• The gaps that exist for your target accounts/customers, and how you can fill those gaps

• What success will look like for your customers once they’re upsold or cross-sold

You’ll also want to consider your reporting

If you have gaps in your reporting, or you’re not sure how you’ll track results from your upsell/cross-sell activities, take a deep breath 😮‍💨 

There’s no pressure to figure this out right away—the best thing you can do is simply start by jotting down what you’ve got, and what you don’t.

Myself and our MOps consultant, Anna Aldred, met up in Q4 of last year and sat down to basically mind-map the current vs. furture state of Lifecycle reporting here for upsell and cross-sell 😊 

We’re not solving every challenge immediately, but it helps to level-set (and be realistic as to what you can do right now vs. down the road).

Some extra hot tips 🔥 

Everything we’ve gone over so far will help get you started with upsell or cross-sell this year 👏 

But I’d be remiss if I didn’t share some additional hot tips and recs.

• Sketch out the current state of how your company upsells/cross-sells

  • This doesn’t have to be perfect—create a quick diagram in Miro, jot it down in a Google Doc, you get the picture!

• Use whatever data you’ve got to establish your Goal and Objectives

  • Goal: pick be a pipeline or revenue number as your north star

  • Objectives: pick 2-3 objectives that’ll help you hit your goal

    • These don’t have to be hard and fast objectives; think of them as paths you’ll take to get to your north star

• Keep target account research low-stress

  • Gather the info you can as a starting point

    • Example: I started by gathering recs from our AEs, then looked at Opps records in Salesforce to determine:

      • Existing customer use cases, renewal dates, key stakeholders, power users, and upsell/cross-sell opportunities

• Start having conversations with your collaborators now

  • Loop in Sales early, so they’re prepared to help you

  • Talk to CS about any reports or data they can share with you right now

  • Ask your Ops folks for access to reports, or to walk you through reporting, ahead of mapping out activities

Or, you can just steal my 2025 Playbook 🥳 

If you do decide to try out upsell or cross-sell activities this year, lemme know how they go!

Many of us learn as we go with this stuff, and while it’s not always easy, you can take a crawl > walk > run approach with it.

Now, I should caveat all of this by saying: your upsell or cross-sell activities may look different from mine. Your company may be at a different stage, or pivoting how it tackles upsell…you name it.

But, you can use the tips in this edition, and the playbook, as a starting guide.

Oh—and you don’t need to be in lifecycle to drive upsell/cross-sell revenue 😉 

Either way, I’m proud of you for driving shmoney for your biz—and making it to the end of this newsletter 🥳 😆 

I’ll be in touch next month with another issue of That Marketing Newsletter!

P.s. here’s what I’m drinking & reading lately

P.p.s. have feedback about this newsletter, ideas to share for future issues, or any gripes? I’m all ears—shoot me an email at [email protected] 👋