HelpSpot In-Depth

HelpSpot Blog: Ian's Posts

Hi! I founded HelpSpot in 2004. This is my little corner of the site to talk about the business of software.

Episode 11: New HelpSpot Pricing

I discuss the new HelpSpot pricing model.

Face to Face

When was the last time you were face–to–face with your customers? For some people reading this the answer is never. For the rest of us it's rarely.

A Challenge: Sell Features, Not Benefits

Focusing your marketing copy on benefits not features is pretty much considered common knowledge these days. Let me push back on that idea a bit.

ABC #9: Rogue One

Taylor Otwell and I discuss the first Star Wars Rogue One trailer.

Ep 10: Matt Stauffer TextExpander Throwdown

Matt and I attempt to be mad at each other while discussing the TextExpander controversy.

Ep 10: Matt Stauffer TextExpander Throwdown

Matt and I attempt to be mad at each other while discussing the TextExpander controversy.

ABC #8: Inside HelpSpot Vault

Get the skinny on our new little project HelpSpot Vault. What it does, how it works, how it connects with building our own business systems and HelpSpot's marketing goals.

ABC #8: Inside HelpSpot Vault

Get the skinny on our new little project HelpSpot Vault. What it does, how it works, how it connects with building our own business systems and HelpSpot's marketing goals.

ABC #7: Should You Build Your Own Business Systems?

Conventional wisdom says you shouldn't build your own business systems like CMSs, stores, etc. Listen to why I think sometimes it's OK to give in to NIH (not invented here).

ABC #7: Should You Build Your Own Business Systems?

Conventional wisdom says you shouldn't build your own business systems like CMSs, stores, etc. Listen to why I think sometimes it's OK to give in to NIH (not invented here).

Nexus And Your Software Business

Every state has it’s own determination of nexus. Yes, every state. So, if your business is like mine and operates in a few states (5 for us) you’ll have to figure this out for each and every state.

Nexus And Your Software Business

Every state has it’s own determination of nexus. Yes, every state. So, if your business is like mine and operates in a few states (5 for us) you’ll have to figure this out for each and every state.

SaaS That App

If you sell on-premise software like we do, SaaS can be a daunting idea. Do you move your software to The Cloud? How? What should you do about your pricing? What technical changes are required? Is it worth the effort?

SaaS That App

If you sell on-premise software like we do, SaaS can be a daunting idea. Do you move your software to The Cloud? How? What should you do about your pricing? What technical changes are required? Is it worth the effort?

How to Get Hired at a Startup

A practical guide on what to do and not do in your cover letter and resume.