Startup Strategy: How to Choose Software Tools for the Long Game

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demo-kitchen

The work involved in getting a startup off the ground can feel, at times, like a never-ending

task. If you’ve ever lived through a kitchen remodel, you know the drill. You start with a dream — a vision of perfection. You have hundreds of amazing ideas. Pintrest boards, if that’s your

thing. Moleskin notebooks filled with scribblings. You look at every kitchen around you with great attention to detail. And then the demo crew arrives, and at the end of the first day, you realize that you no longer have a kitchen, and that you may well be in just a little bit over your head.

No matter how carefully you’ve planned, there are a million tiny decisions that you need to make — and you never actually know about those decisions until right before you need to make them, and you can’t reach your spouse, so you have to just decide — by yourself — if the faucet should be in the middle of the sink, or off to the side, and which side, and do you want a hole for a filter tap and another one for an instant hot water tap? These decisions seem extraordinarily important at the moment you have to make them, and you are terrified that a wrong answer will mean not just an inefficient kitchen, but perhaps the end of your marriage.

I’m the VP of Engineering for a mobile enterprise app, Acompli. And because we’re talking about my company here, I could not afford to fall into the kitchen remodel trap. I needed to get the basics up and running immediately.

I needed tools that were proven, that I could set up instantaneously, and that my people could use right away. But those tools also needed to scale with us and let us grow without switching out a system for something new in the middle. The company had to be ready for the million tiny decisions we’d need to make. We didn’t want to turn down amazing opportunities just because they came our way too early.

bitbucket_logo

So we started with familiar tools, things we’d used before: JIRA for issue tracking, Github for source.

There are two related — but distinct — points that I want to make here:code management. We knew that they worked well together, and we already knew how to use them. Following that line of reasoning, we thought that we’d want to use Github for hosting — after all, it’s a bit famous, plays nicely with JIRA and is the developer favorite. But Bitbucket offered better Atlassian integration (as we use Hipchat, Confluence and Bamboo as well), which made it a better choice for us. That was a conscious decision we made, because we weren’t only looking for best of breed solutions, but also for ways to leverage pre-integrated apps.

1. You must have a strategy in place for choosing the tools you use daily in your business.

As I already mentioned, we knew we needed familiar, scalable tools that would work smoothly and effectively together. That was our strategy, and it was because we had this strategy in place that we were able to make the decision to go with Bitbucket over Github for source control. Having a clear strategy has also guided hundreds of other tiny decisions that I face daily. When you know your own strategy, you can face every single decision with significantly more confidence, because you can simply ask yourself: Does this choice fit in with my strategy? The answer to that question will lead you to the right decision.

My second point might seem like an extension of the first, but it also stands on its own:

2. When you’re choosing the tools that will form the backbone of your business, you can’t just consider each one in isolation.

The point here is that you can’t just go for the software that gets the best reviews in each area and smash them together. I mean, you can, but what will you be getting? Your smorgasbord of bests-in-class may each look fantastic when displayed individually, but together they may turn into an absolute mess.

The thing is, this rule doesn’t just apply to the software you choose. It applies to all the decisions you make about your business. None of these decisions are made in a vacuum. Each has implications that affect other parts of your business. So it’s important to make sure that trustradius_logo_tm_1200your strategy takes into account the way the different decisions you make play out across the entire face of your business. A great new tool I’ve started to use is TrustRadius, which provides reviews of popular Enterprise Software with a Yelp-like user experience.

Protip: you need to be able to count on the software and services you choose for your startup, so when in doubt, go with the more established player. Yes, it’s great to support other startups, and if there’s one that meets your needs precisely, give it a whirl, but be aware that you’ll have to be vigilant about followup to make sure things work the way they’re supposed to. In situations where you don’t have time to oversee the solution — or you just need something to work without any extra intervention, go with one of the larger, more established vendors. The peace of mind you’ll enjoy will far outweigh any price discrepancy.

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Kevin Henrikson

Kevin Henrikson

Co-Founder Acompli (now Outlook iOS/Android) at Microsoft
Kevin Henrikson leads engineering for Microsoft Outlook iOS/Android. Previously, he co-founded Acompli and ran engineering prior to an acquisition by Microsoft in 2014 for $200M. Before Acompli, he was an Entrepreneur-in-Residence for Redpoint Ventures, a venture capital firm for early stage technology companies.
Kevin Henrikson

@KevinHenrikson

Outlook @microsoft was Co-Founder @acompli, EIR @redpoint. my favorite ceo @itsduhnise
RT @MPalermiti: “@Outlook mobile is being used on more than 100 million iOS and Android devices.” - @satyanadella on yesterday's @Microsoft - 1 day ago
Kevin Henrikson
Kevin Henrikson

2 thoughts on “Startup Strategy: How to Choose Software Tools for the Long Game

  1. Vinay Bhagat

    Kevin – I’m really glad to hear that you have found value in TrustRadius. Thanks for citing us in your blog post. I welcome any feedback you may have.

  2. Eric Metelka

    Great post, Kevin. Finding the right tools for your business, especially a startup, can save you a ton of time. There’s also a lot of cost associated with switching products often.

    I think it’s also important that you can segment the right tools for your business size. Many of those established players you refer to only have pricing for large enterprises. There’s a need to find out what other startups and small businesses are using for their tools. It’s something you can do on G2 Crowd. For example, we have Bitbucket reviews that you can filter by size of companies so you can focus on what people in companies like yours are using. I hope you find it helpful.

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