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What types of management problems plague startups?

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Being an avid reader of Fred Wilson’s AVC, I’ve learned much over the years. And one thing he underscores is that *ideas* are a dime a dozen. And that great investments are in team & execution.

Join 38,000 others and follow Sean Hull on twitter @hullsean.

As a long time consultant, I’ve had the good fortune to see a lot of startups under the microscope. If you work a FT role for 2 years, over a decade you may work at 5 companies. In the same amount of time, i’ve worked at over 65 companies.

In those years I’ve encountered great teams that are super organized, and continue to move the product forward. But I have also seen a number of symptoms, that caused the business problems, and slowed down their march forward.

Low morale

One firm I worked at a few years back was in the space around education, specifically with a lot of microlearning products, with big customers doing corporate onboarding.

Their sales team was world class, closing bigger and bigger deals, but engineering had terrible and festering problems. As it went, they grew to have hundreds of employees in a matter of a year or two. Meanwhile the CTO was not a big people person. He didn’t like speaking in front of large groups, nor was he very hands on. As a small ten person startup he was super technical and talented, but as the company grew so fast, it left a leadership vacuum.

And then some bad hires grew the engineer team fast. But internally there was a lot of infighting. The original founding team worked hard and had strong direction, but the new hires all vied for control. And the ugly personalities reared their heads.

After a few short weeks, half the engineering team quit, in a matter of days. A tough blow to a team already struggling to keep up with growth.

It is not easy to right a large plane in mid flight like that, carrying plenty of technical debt besides.

Related: A CTO must never do this

Bad alignment

Another place I had the pleasure of working at was a well known digital media brand, that expanded into film production, recording and even investigative reporting. For all it’s wide ranging efforts, it presided over a huge growth business, with seemingly unlimited revenue. Impressive to be sure.

On the technology side, however things were not so sunny. As their business grew, they planned to consoldate data from many disparate divisions. And this is a process that many growing businesses go through. Finance in one platform & database, bookings & production in another, while analytics and viewer statistics in yet a third. But how to report on all of that data?

As a special crack team of big data experts, we were assigned the task of building out this centralized repository of business truth. And as we built and architect that system, we needed to work closely with the operations division.

Now in this business, they were using public cloud, Amazon Web Services like many other startups. However they had a separate team of devops who presided over these accounts.

As our team was handed strict deadlines to deliver working reports & systems, we had conference calls with the Devops team. However that team was not on board with those deadlines. They pushed back and claimed such systems would take months to setup.

As we explained expectations being pushed on our shoulders, Devops said “just push back and say no”. They advised that we “send it back up the chain”

But what if there’s a chink in the chain?

Clearly the two teams were not aligned at all on deadlines & deliverables. And that’s not a fault of either of those teams. It straightaway falls in the lap of management to align those.

And we were somehow stuck in the middle. Ugh!

Related: How to avoid legal trouble in consulting

Loose discipline

One startup I worked at had a security and authentication app.

Here teams were fairly happy on the whole. In fact they raved about having a great boss. Indeed the boss was a very kind leader, understanding, patient, and hardworking.

However, over and over, we lacked a “decider”. Here other team members were giving each other tasks. Promises were made loosely, and then forgotten one or two weeks later. And a constant lack of direction dragged down delivery.

For my money, a promise to have a meeting at 10am, is one all parties should abide. Whatever their level in the business. Not be late, have excuses about trains, or simply skip the meeting with no explanation. These types of habits cause the team to grow weary, and lower the bar of expectations.

Frustrating indeed.

Related: When you have to take the fall

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All CTO/CIO Scalability Startups

Why Scalability Is Big Business

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1. Complexity Is Growing

Despite automation & the mass migration to the cloud, or perhaps because of it, complexity continues to grow. Back in the dot com era a typical infrastructure included a load balancer, a couple web servers, one oracle database, and that was pretty much it.

Now that has multiplied. Pile on top of that three to five more webservers, a search server, a page cache, an object cache, one or more slave databases and more. You may have a utility server with jenkins for continuous automation, monitoring applications like nagios and cacti, your source code repository and perhaps configuration management like Puppet or Chef.

That’s not only more moving parts, it’s a wider swath of skills and technologies to understand. That’s one reason Generalists Are Better At Scaling The Web.

Also: Are SQL Databases Dead?

2. Developer Mandate: Features

The pressure to build features that can directly be monetized is obvious. Startups especially have the pressure to grow fast and grow now. So security, technical debt, and scalability often take a back seat. What’s more in small scrappy and lean startups, ops sometimes falls on the shoulders of one competent but overworked developer.

Related: Why Oracle Won’t Kill MySQL

3. Startups Growing Pains

With hyper growth, startups can go from 100 customers to millions overnight. That kind of popularity is a good problem to have. But if your app hits a wall and suddenly falls over, everyone is scrambling. The pressure builds, as fear of losing that traction mounts, and heads are put on the chopping block.

Read: AirBNB Didn’t Have To Fail

4. Missing Browse-only Mode & Feature Flags

Ever been browsing for airline tickets, then go to order and get an error? Try again later? If so you’re familiar with a browse-only mode. This is a very powerful addition to any web application but is very often left out. Some mistakenly believe it won’t work for their application, as users will always be changing data.

Ever visited a website that has star ratings, only to find them missing? Or temporarily unable to edit your rating for a piece of content? This amounts to what’s called a feature flag. These powerful switches give operations teams the ability to disable heavy features, while the side is under tremendous load. They can take a huge burden off the shoulders of your servers when you hit that scalability cliff.

Check this: Why I Don’t Work With Recruiters

5. Operations as an afterthought

I outlined some of the top reasons Why Startups Desperately Need Techops. It is a repeating refrain. Priorities of a growing startup often involve taking on technical debt. But if that isn’t managed carefully you’ll run into some of the problems that Ward Cunningham Warns Us About.

Also: 5 Things Are Toxic To Scalability

Get more. Grab our exclusive monthly Scalable Startups. We share tips and special content. Our latest Why I don’t work with recruiters

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Half of NYC Fastest Growing Firms In Tech


If there was ever any question about the exploding tech scene in New York City circa 2012, check out Crains recent 50 fastest growing firms.

#3 Thrillist

City guide & lifestyle site for men.

#5 Usablenet

Provides a powerful platform for content delivery to mobile & tablets as well as laptops.

#8 Admarketplace

A leader in search syndication.

#9 Yodle

From the bloodbath of newspaper classifieds brought on by disrupters like Craigslist & eBay, comes a new breed of online advertiser catering to customers and the digital space.

#15 Telx

Provides datacenter services such as high speed connections, private clouds, servers & networking equipment.

#16 Complex Media

An online style and lifestyle magazine catering to young men.

#18 Wavsys

Finding talented mobile engineers isn’t easy. This firm provides contractors for the big wireless firms.

#19 Return Path

Helps firms with email delivery, by routing around and through spam filters.

#20 M5 Networks

Cloud Based phone systems.

#22 Mitchell Martin

Tech staffing and consulting solutions

#25 Artech Information Systems

Staffing for technology and project management requirements.

#27 Infinity Consulting Solutions

Recruiters for the technology industry as well as finance and accounting firms.

#28 Vicom Computer Services Inc.

Providing high end IBM enterprise solutions to datacenters.

#35 Direct Agents Inc.

A fast growing digital marketing firm.

#37 TTI of USA

Another staffing & consulting solutions firm for technology firms.

#41 [email protected]

Bringing better customer service to technology consulting & services industry.

#44 Insys Group

Technology consulting and services.

#46 Travelclick

Provides technology solutions that help hotels increase revenues.

#48 Tekserve

Apple products repair & servicing.

#49 Axispoint Inc.

Business technology services and solutions.

#50 Paradysz Inc.

Email & social media marketing company