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Six Great Pieces of Advice for Startups from 2015 (And a Bad One)

Kirsten Charlton, AVP of CNA Insurance’s technology division, gives her advice on insuring a startup company in Built In Chicago’s article by Andreas Rekdal.

Content from Built In Chicago by Andreas Rekdal

Sometimes the hard way is the only way to learn. But when you're building a business, those hard-earned lessons can be major time sinks that may end up costing you your savings — or worse yet, your reputation.

To help early-stage startups avoid costly mistakes, we asked leaders in the Chicago tech community what advice they have for newcomers. The insights they offered this year covered every aspect of growing companies and gaining traction in the marketplace, from recruiting to customer service, insurance, and search engine optimization.

Here's what they had to say.

Help your customers help themselves
Customer service can take a major toll on your resources, so before launching a new product you need to ensure you have everything in place to mitigate the inevitable flood of questions. One way to do that, according to Nicole McCloud of Desk.com, is to make sure the information customers need is readily available on your website. Landing pages, customer portals, FAQs, and customized articles can all help streamline the customer support process.

"When you're a new company, you need to help your clients find the answers they need quickly or they could leave and go to someone else," said McCloud. "Take the time to build out a robust knowledge base to empower your customers to help themselves and get immediate answers to their questions."

How to compete with larger companies for interns
"Really let candidates know they're going to make a difference in the company," said Yello CEO Jason Weingarten. "People will know their name, and they won't have to wait three years before one line of code makes it into production."

If you're looking to attract candidates who are also considering enterprise opportunities, Weingarten said to emphasize how the hands-on aspect of working for a startup can foster a more immersive learning experience than an internship with a large company. All of his interns have worked on features that ended up in the finished product — an achievement that's harder to list on a resume if you're one of 500 interns during a single summer.

Laser-focus on the problem you're solving
Although originally offered by GiveForward CEO Desiree Vargas Wrigley as advice for getting into and thriving with Techstars, having a clear message about the problem you're solving is crucial for every startup. Without a clear and concise articulation about the need for your product, you'll have a hard time getting busy investors and potential customers on board.

"We knew it could be confusing to explain every idea we'd ever had, so by keeping conversations on our one focus, it allowed us to demonstrate our mission better," said Vargas Wrigley.

Don't make hires you'll come to regret later
When your company is rapidly growing, you may find yourself tempted to take a chance on an applicant you wouldn't otherwise have hired. mLevelCEO Dave Cutler cautions against hiring anyone who isn't a perfect fit.

"Finding the right person is always more important than finding a person," said Cutler.
Having been involved in organizations that have grown faster than they were prepared for in the past, he speaks from experience. Besides productivity losses, Cutler points out that bad hires can have a negative impact on culture, and ultimately future growth.

Get insurance
Realistically speaking, many early-stage startups are at risk of going under if a major unforeseen circumstance arises. From data breaches to problems with your code, insurance can provide you with peace of mind and a ready-made legal defense team.

"When tech companies start out, it's typically one person with an idea," said Kirsten Charlton, AVP of CNA Insurance's technology division. "They run very lean companies. They don't need a lot of infrastructure or resources, and insurance is often the last thing on their mind. But in reality, it's the first thing they need."

Make sure potential customers find you
Colin Guidi, Director of Search Engine Optimization (SEO) at 3Q Digital, said some companies update their sites once or twice yearly to meet updated SEO best practices and proceed to ignore their content for the remainder of the year. But that's not how SEO works best — especially in an age of continuous algorithm tweaks and tests.

Instead, SEO is most beneficial when it's used as an ongoing engagement. That means developing fresh and frequent content updates that work for today and predict the needs of tomorrow.

"Your site content will change," Guidi said. "You might acquire an offering and need help promoting it. An algorithm update will come along and knock you ship/website off course. SEO should not be reactive but rather proactive."

Bonus: The worst advice Punchkick Interactive's CEO ever heard
This year, we also published a list of the worst pieces of advice Chicago startup leaders ever received. Here's Punchkick Interactive Inc. CEO Zak Dabbas' story:

"I received some awful advice from someone close to me a few years ago. This person told me that it would be a big mistake to let my employees see me as a peer, as it would 'erode my leadership ability's with them. He also advised me to keep a certain amount of distance between myself and our staff, so that they wouldn't take advantage of our friendship and cut corners. I now realize that he was completely projecting his issues onto me. Many of the folks I work with at Punchkick are my closest friends in the world, and I thrive on our working together as peers, friends, and in many cases, like family. I've found that by opening up about both the good and bad issues facing the company, I'm able to rally excitement and a team dynamic I've never seen in a company before. I can bring my whole self to work, flaws and all, and find support and strength in the team around me. Nearly every step I've taken to be transparent and vulnerable with those I work with has rewarded me in ways that I can't describe. The camaraderie and sense of family at Punchkick is worth more than any other professional accomplishment I've experienced."