Mid-Market Sales: How to Convince Your Customers to Upgrade

Most sales teams dream of closing a multi-million dollar deal
with a Fortune 500 company. While one major sale can help a team
reach its annual quota, getting a major deal without an established
relationship is difficult at best.

Unless you also work for a Fortune 500 company, It might be more
realistic for marketers and sales teams to target small to
medium-sized businesses (SMB). It makes sense to focus on SMB
because often this group needs the most help and could benefit
greatly from your services.

Keep in mind, however, this group often has less money to spend,
meaning their purchases are smaller. It takes more sales to really
make a difference for your bottom line.

Still, marketers can often find the most success with mid-market
sales. Medium-sized companies generally have the same needs as
enterprise businesses, but the budgets of small businesses. If you
target several successfully, your sales team could close a number
of decent-sized deals.

Read on to learn why mid-market sales are an important part of
your marketing strategy and how you can convince those customers to
keep buying.

Why mid-market companies are an important audience

Mid-market sales might not be the largest business deals inked
each year, but these types of sales might be more common than you
considers medium-sized businesses companies with between
100 and 999 employees. In the IT sector, this segment is expected
to make up about two-thirds of all SMB sales through 2021. That
adds up to more than $400 billion in transactions.

Plus, the corporate landscape is always changing. Most of the
world’s largest and most successful companies began as startups
and medium-sized businesses before reaching the level they are
today. And some companies that seem successful may not be.
reported in 2016 that half of the companies that made up
the Dow in 1995 no longer existed 20 years later. Some of these
companies merged with others to form new brands, some went out of
business, and others simply didn’t exist yet.

It can be difficult to know which companies will be the most
successful. If you begin a business relationship with a smaller
company and provide the services and products they need, they might
continue buying from you as they grow larger. The bigger they get,
the larger the deals could be.

Upsells and renewals are cost-effective strategies for mid-market

Most companies are looking to expand their current client list,
but focusing solely on attracting new customers isn’t always the
most cost-effective strategy.

Researchers found that among SaaS companies with more than $2
million in annual revenue, it cost almost five times as
to close a deal with a new customer compared to upselling
an existing client. The customer acquisition cost was similar for

Chart showing customer acquisition cost for new customers and existing customers

Source: For

In addition to costing less, repeat customers are more likely to
spend money. The Harvard
Business Review
found that improving customer retention by just
5% increases profits anywhere from 25% to a staggering 95%.

How to encourage your medium-sized customers to upgrade

The question remains: How do I boost mid-market sales through
upgrades? Because even when customers want to upgrade, there’s
often still something (or a few things) holding them back.

Here are five tactics you can use to convince your customers to
upgrade and increase your mid-market sales.

1. Change the conversation

You might have to change your messaging to better resonate with
customers, especially if you’re trying to get them to upgrade
their service. When marketing to new customers, you’re focusing
on the general benefit of what your company has to offer.

However, your existing customers are probably already familiar
with your services. They need to hear about how upgrading would
make their lives easier and improve their productivity. (But
remember, your marketing materials can’t always be promotional:
They should also benefit your readers.)

Speak directly to the pain points they currently have, even with
your service. You don’t want to make it seem like your existing
service can’t get the job done, but you need to explain how
adding new services can reduce additional stressors.

Consider using the
Challenger sales model
, which poses the worst-case scenario
first and then explains how the problem could be avoided with your
extra services. Rather than just explaining the benefits of your
upgrade, this scenario puts it in a real-world situation to which
your customer can relate.

2. Get more detailed in your segmentation

is nothing new to anyone with experience in email
marketing. You don’t have to be sending emails to use this tactic
to increase your mid-market sales. A lot of companies will use
basic segments based on customer size, location, industry,
activity, and other behavioral or demographic attributes.

When pushing for upgrades, you need to really dig in on the
segmentation. For example, a law firm with 200 employees that needs
improved document solutions is very different than a tech company
with 750 employees that needs to better integrate its CMS into
other applications. Consider grouping your upgrade candidates by
company size, revenue earned, pain points, and specific business
needs. This will help you deliver more targeted messages that speak
directly to what they require.

3. Use email automation to nurture active leads

Once you zero in on your messaging and segmentation, you should
create lead nurturing campaigns using email automation. Use

customer journeys
and drip campaigns to send emails based on
web or app behavior. As your customers move along their journey,
you’ll develop more qualified leads that are more likely to

It’s important to remember that lead nurturing emails aren’t
always designed with sales in mind. Consider this great lead
nurturing example from

Email example to promote a customer service report

Really Good Emails

Here’s a great strategy to follow up this email. Set up your
drip campaign workflow so an email goes out a few days later to
everyone who opens the report. The email should include a subtle
push about how your next-tier solutions address some of the
customer service pain points mentioned in the study.

4. Use sales prospecting to re-engage with cold leads

We’ll admit that sales prospecting isn’t always the best
strategy to use when searching for customers to upgrade. In most
cases, this tactic has the same results as a cold call or
reactivation email campaign. However, you can make it work for you
if you play up the FOMO factor in your communications.

The airline industry does a great job of using this type of
psychological marketing in the following email.

 Email example that reminds contact to use airline frequent flier miles before they expire

Source: Really
Good Emails

Treat your initial sales prospecting email or phone call with
your customer more like you would a new client. Learn if their
needs have changed or if they have new pain points. From there, you
can let them know about the service or product upgrade that
competitors in their space are already using. This might be enough
to encourage them to think about your offer.

You can also update their segmentation if necessary to ensure
they start receiving more relevant information.

5. Offer a free trial or demo

Even if you’ve said all the right things and nurtured your
customers exactly as you should, sometimes it’s best to let your
clients try out a new or upgraded service through a free trial.
Once they can understand how beneficial your service can be, it’s
often difficult to say no.

In fact, a recent survey by
found that about two-thirds of B2B subscriptions that
started as a free trial converted to a paid service.

It’s important that you stay in touch with your customers
while they’re still in the trial phase to answer questions or
provide additional insight about your services. B2B customers who
are contacted by a sales rep during their free trial were
70% more likely to convert
than those users who were not

Wrap up

You don’t need to close a major deal with an enterprise brand
for your company to be successful. You can focus on your existing
customers and benefit from mid-market sales. Even if your clients
are hesitant to upgrade, you can encourage them by using one of the
following tactics:

  • Focus your marketing efforts on their pain points and how your
    upgraded service can make their lives easier
  • Hyper-segment your efforts based on business size and specific
    needs so you can create more personalized communications
  • Create automated email drip campaigns to reach your specific
    segments at specific times based on behavior to generate more
    qualified leads
  • Let your customers test your product or service for a free
    trial or demo
    Add these tactics to your retention marketing plan, and you’ll
    begin to see your mid-market sales increase.

Are you ready to effectively use email to nurture your leads and
generate more mid-market sales? Sign up for free and
try our email platform today.

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Mid-Market Sales: How to Convince Your Customers to Upgrade

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Mid-Market Sales: How to Convince Your Customers to Upgrade