Securing the Five Figure Sale

My ebook on how you can sell into the enterprise as a bootstrapper is up on Product Hunt. It’s free and covers a lot of the nuts and bolts you won’t normally find in blog posts, etc.

This is the playbook I’ve run for the past 12 years with HelpSpot.

I’m especially looking forward to any feedback the family has.


I’ve started reading it. Looks nice so far!

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Ian, you do a great job of educating how slowly and painfully things can move when selling to the enterprise. A keyword for selling to the enterprise is patience. People inside the enterprise themselves get frustrated with how slow things go and are grateful for vendors who understand and work with this.

Re RFP: a good technique is to ask the contact at the enterprise how many people have received the RFP. Often the answer tells you straight away to not bother.

Who did your proofreading? For a self-published, free ebook, the copy was surprisingly free of typos. (Although page 29: "If there isn’t, "). If the proofreader is an independent freelancer, could you please PM their contact details?

Are you trying to sell anything in particular to the readers of the ebook? If so, it wasn’t clear to me. That may be your intention - subtlety does seem to be in short-supply amongst people conducting online marketing.

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Thanks Steve. That’s a good idea on the RFPs.

The company that did the editing and design is a larger org. Happy to put you in touch, but I don’t think they really do one off proofreading of smaller things though if you’re looking for the full ebook treatmeant I’m sure they could help.

I’m not trying to sell anything! I had some various ideas around it, but in the end I figure it can help build my personal list a bit which I’m trying to do more with and basically just give back.

Speaking of… - handy stuff.

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I have downloaded it, but no read it yet…

@ian, thanks for this, it looks quite interesting, I just downloaded it and plan to read it during the week. I’ll give you feedback later.

Reading it, very-very interesting.

However, reading PDF on a phone is a major bottom pain! Why PDF, man, eh? To stay in the enterprisey character? :slight_smile:

From inside of BigCos, I very much confirm the longer trial length required by enterprises. Months and months.

Ian, sorry - would it be possible to reformat it into fb2 or epub?

Shame on me, but I cannot finish the book for a few month already - because I can only read it on the computer. Just like many other people, when I’m in front of my computer, I have stuff to do, and have no time to read. When I have time to read, I usually only have my phone.

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Programs such as GoodReader can crop out the margins of PDFs, making them easier to read on the phone. Depending on how the PDF was created, you may also be able to reflow the text: