Ah, the elusive and lucrative Millennial market. Such a tempting conquest, yet so frustrating to conquer.

Connecting with this demographic is not easy. As the first digitally native generation, Millennials have been raised on technology and live and die by social media and their smartphones. As for engaging with brands, they generally have a sharper eye and higher expectations than generations before them.

To help you win over this tough crowd, we surveyed Millennials about their marketing preferences, and we have four major insights to share.

1. Brands must deliver authenticity

Millennials expect authenticity. Wait, I take that back. They demand it. And we marketers need to deliver it. Millennials have little patience for marketing that feels phony: A few examples that Millennial respondents provided as the worst offenders include ads for perfume, pharmaceuticals, weight loss, and yogurt.

The list goes on to include ads that use conspicuous commercial actors and call them real users, and ads that rely on cheesy jingle-like music and images of fabricated happy families around the dinner table.

Also consider that Millennials care deeply about social responsibility—more so than any other demographic, according to a 2014 survey by the Nielsen Global Survey Group. If you are perceived as trying to capitalize on important social issues inauthentically, Millennials will notice—and they'll raise an eyebrow. So before you launch into a social campaign, make sure that there's serious commitment to the cause.

How does authenticity apply more specifically to the B2B marketer? It means ditching those canned sales emails. If Millennials could swipe left on your sales email, they would. Instead, read up on social selling, a more Millennial-friendly way to engage your sales prospect because you take the time to get to know them and engage with them before you go for the sale.

2. Your brand must look the part

If you're a Gen Xer, the 90s might feel recent to you, but to most Millennials it was a lifetime ago. To attract Millennials, whether you are a B2B or B2C marketer, it's worth investing in bringing the design of your brand up to date.

As savvy digital content consumers, Millennials are especially attuned to best and worst design practices. Among the most common, and most awful, design wrongs are these:

  • Clipart images
  • Generic stock images
  • Blinking links
  • Old typography
  • Extreme gradient backgrounds
  • Microsoft Word clipart aesthetics

Graphic design can be a great tool to help you connect with Millennials in a way that feels true to your values—and theirs. And don't be afraid to show your fun side; playing it safe will not earn you any brownie points.

3. Marketing can't be too aggressive

A 2014 survey found that 84% of Millennials don't trust advertising—popups, calls, traditional ads—that puts them on the defensive by aggressive means.

Millennials need to trust you are authentic, but they also need to respect your brand before they can purchase from you. Aggressive sales methods will therefore be counterproductive and will cause Millennial customers to disengage from your brand.

Here are examples our Millennial respondents cited as no-no's:

  • Ads that follow you around the Internet. Although this "retargeting" or "remarketing" can be effective, overdoing it might be easily perceived as stalker-like.
  • Ads that block the screen or the main content the user is trying to access.
  • Popups that prevent the user from exiting a window.
  • Websites that try too hard to get your email by popping up the email capture too often.
  • Clickbait articles with sensational phrases like "You won't believe what happened next!"

4. Engage through genuine, value-adding content

Providing value-added content is a strategy relevant to both B2B and B2C marketers.

HubSpot, which provides inbound marketing and sales software, essentially built an entire category through its approach to value-added content. Invision has also done a nice job using content, and has gone so far as to produce a globally distributed film. Both companies are thoughtful about the content they create—and, even more importantly, on how they distribute it to prospects through social media, influencers, mobile, video, and other Millennial-friendly channels.

On the B2C front, take a cue from Glossier, the online beauty products retailer that set themselves apart through cleanly designed product packaging and creative content marketing. The company was founded by beauty editors who capitalize on their expertise by sharing insider knowledge of the industry on the Into the Gloss blog. Featuring fashionista interviews and expert tips, the blog keeps users on the site and often transforms them into customers through inspiration and expert support—a technique decidedly more effective than continually reminding them that their shopping cart is empty.

* * *

Connecting with Millennials can be daunting, but it is not impossible. When you earn their trust with authentic messaging and you apply a Millennial-friendly marketing approach, you can count on them to stick around—and sing your praises with their social media and smartphones.

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image of Pamela Webber

Pamela Webber is chief operating officer of 99designs, a global creative platform that makes it easy for designers and clients to work together to create designs they love.

LinkedIn: Pam Webber

Twitter: @pamwebber_sf