6 Simple Selling Tips For Software Entrepreneurs

About This Blog

This site is for  entrepreneurs.  A full RSS feed to the articles is available.  Please subscribe so we know you're out there.  If you need more convincing, learn more about the site.



And, you can find me on Google+

Connect on Twitter

Get Articles By Email

Your email:


Blog Navigator

Navigate By : 
[Article Index]

Questions about startups?

If you have questions about startups, you can find me and a bunch of other startup fanatics on the free Q&A website:


Subscribe to Updates


30,000+ subscribers can't all be wrong.  Subscribe to the OnStartups.com RSS feed.

Follow me on LinkedIn


Current Articles | RSS Feed RSS Feed

6 Simple Selling Tips For Software Entrepreneurs


The following is a guest post by David Mytton founder of Boxed Ice, which provides software for server monitoring.  Deep down inside, many software entrepreneurs really dislike selling.  This article provides some practical tips for “selling without selling”.  That is, ways to avoid having to be that stereotypical "sales guy". - Dharmesh

"Sales" is sometimes perceived with an aura of mystery. As a developer, it's something I always assumed was reserved for a "real salesperson" and even though I was selling our products, I thought it was because the customer had come to us directly. Whilst there is an aspect of "sales" that involves cold calling and making visits to prospects, I actually recently realised that many of the things I'm doing on a daily basis are all part of what might be called "sales".onstartups sales guy

What sales activities consist of will differ depending on what you're selling, who you're selling to (consumers, smaller businesses or enterprise) and how large your organisation is, but there are a few things that can be used universally and to great effect. Here are a few that I use with my own SaaS product.

1. Signup followups

Getting a customer to sign up is a major step but it's not the end of the process - you need to make sure they're actually using the product. E-mail them the next day to remind them of a few of the cool features or recommend things to try. Being smart about it helps - you can easily track whether they have logged in and performed various tasks so include those in an e-mail.

In our case, the e-mail subject is "Have you tried our iPhone app?" and the e-mail highlights the advantages of the free app, with a link to the iTunes Store, plus a reminder of the web UI URL for their account.

In the early days, I used to phone every one of my signups to see how they were doing. We don't collect the phone number as part of the signup process but many customers add it because our product allows for SMS alerts. This helped get early feedback and users were often surprised to get a call before they'd even paid anything.

2. Trial followups

All our users sign up to a 2 week trial before they have to pay. An e-mail is sent to remind them the trial is expiring 2 days before, and we e-mail them again on the day of expiry. The key thing here is to ensure the user has time to upgrade, sometimes requiring internal approval. All our trials are set to expire on a Thursday i.e. mid-week. This means expiry notifications go out on a Tuesday. This avoids being lost in the Monday e-mail overload from the weekend and avoids Fridays when people just want to go home.

And because most of our users are in Europe or the US, we time the e-mails to arrive during the afternoon/late morning rather than overnight. Users will clear out their inbox in the morning so this leaves them clear to receive our e-mails!

3. Mixing automation with real people

I think you're more likely to look at an e-mail that's from a real person than one obviously from a machine "From: David Mytton" vs "From: Boxed Ice Mailer". I mix these up so the day after signup followup comes from "me", is written in a casual style and signed off by me. It also comes from my company e-mail so replies go directly to me and because I'm asking a question about using our iPhone app, I often get replies with feedback or questions.

But our trial reminder e-mails come from the system. You'd expect these to be automated whereas an e-mail asking how things are going is more personal.

4. Making automation interesting

Our signup e-mail with the user's login details and the trial e-mails are sent by the "Boxed Ice Robot Llama". This makes it a little different from other automated systems and we've had some good feedback from users enjoying this differentiation. It all goes towards making the service a little more friendly and has been used to good effect by the guys at Moo, who use "Little Moo" as their order processor.

5. Highlighting the higher value customers

Our product is a server monitoring service so the more servers you monitor, the more you pay. We run a script to highlight users on the trial with more than 3 servers and add a task to our customer system to get in touch with them directly before their trial ends. This will be a phone call if they have provided their details, or we'll e-mail them. This comes directly from me as a real person, asks how they've been getting on, whether they're going to upgrade and includes volume
discount pricing.

I've found that some users do plan to upgrade their accounts but haven't had time to, or have a few questions first. Often these will get pushed to the end of the todo list so getting in touch directly allows you to speed up the sale. You can also be flexible with your
pricing to offer discounts if the customer agrees to a minimum number to get access to the volume discounts in anticipation of future growth, or if they're willing to pay in advance for a discount.

6. Convert With Newsletters

All our signups get subscribed to our monthly newsletter which contains not just product news but interesting links from our blog, Twitter and around the web. We've had many cases where the user has not converted from the trial immediately, but months later they come back when a feature they wanted has been implemented having found out from the newsletter.


Although this doesn't fit with the stereotype of the hard sell from the sales guy who just won't give up, these are all legitimate "sales" activities that can be done by any software startup and can easily scale as the customer base grows. We've only recently started highlighting the higher value trial users but this has already proven to be worthwhile. So let me know what you think and what's worked for you in the comments.

Posted by Dharmesh Shah on Fri, Aug 20, 2010


I really liked the idea of optionally collecting their mobile phone number for SMS updates. The thought of a person-to-person call is intriquing. Certainly it's easier with start-ups since you're not buried in customers (yet).  
I also liked the idea of trials ending on Thursdays, with notices going out on Tuesdays. This avoidance of Monday's and Fridays (and weekends) seems to be a very good thought.  
Thanks for posting, David (and Dharmesh).

posted on Friday, August 20, 2010 at 3:09 PM by Shawn Anderson

Interesting article, although it appeared to be geared more toward how to follow up on leads, rather than selling. I would also add: 
Demonstrate the economic value to the customer - what are they saving or gaining in dollar terms (or expected value) 
Ryan Malone 
SmartBug Media 
An inbound marketing agency and Hubspot Partner 
Free reports: 
Elder Care Marketing Industry Report 
7 Tactics to Boosting White Paper Performance 

posted on Friday, August 20, 2010 at 4:29 PM by Ryan Malone

Good post for bring to light tha sales needs to be a well thought out process. It always interesting to see an entrepreneur without a sales background suddenly thrust into a sales role, only to discover (and appreciate) that sales is a well orchestrated process.  
Sales is much like product development where products are defined, implemented and tested. What you say, how you say something, and when you say it to a prospect can be the difference between a sale or not.

posted on Saturday, August 21, 2010 at 7:17 AM by Cynthia Kocialski

The sales process is entirely different for a B2C versus a B2B. And when you're selling "enterprise software", the differences are even larger. 
I started my company with the thought that if you create a killer product, it will "sell itself". We created a killer product, our customers LOVE our software...but what i learned was that Enterprise software never sells itself. Over the last 3 years, I've come to appreciate what a good sales person brings to the table. It is NOT a skillset that the entreprenurial developer has!! If you're selling software that people can sign up directly for..then that's not a problem. But if you are selling into large, complex organizations...trust me, a talented sales person will make all the difference.

posted on Saturday, August 21, 2010 at 12:47 PM by Michael Hennessy

Don't forget to just ask for the sale -- sometimes it really is that simple.

posted on Saturday, August 21, 2010 at 9:34 PM by Steve @ SmoothEntrepreneur.com

Great post and a process we're just finalising at the moment, however now some changes :) 
We currently offer a "Free Trial" we don't say for how long but we typically allow the pilot to run for 30 days, I've heard of other businesses having 14, and 7 days - but how does one decided which is best for their customers?

posted on Monday, August 23, 2010 at 3:51 AM by James Fletcher

I agree with many of these tips - although many should probably be categorized as marketing. 
These tips will help ease the small startup into the world of sales, and I believe that no matter who the founder is, they must get into sales. As you mention, this is something that tech founders often avoid because they don't understand it and have a specific ideal or view of what selling really is. 
To the comment that a killer product sells itself, you found out the hard way that this is often not true...especially in the enterprise. You must learn about decision makers, authority, budget process, competitive positioning, etc. 
But I do believe that a tech-oriented founder can learn this. And I'm speaking from experience!

posted on Monday, August 23, 2010 at 10:31 AM by Chris Hamoen

We always try to avoid the weekends, the Fridays, and the Mondays. No one wants to spend money on Monday, and people are too busy thinking about the weekend to bring out their credit cards on Friday. Great article.

posted on Monday, August 23, 2010 at 5:19 PM by Jon Marus

Though so many people hate to do selling -- how many people put "salesman" on their business card? -- selling is critical to every company. What many people don't realize is (a) we all like to BUY stuff (so selling stuff shouldn't be so bad), and (b) if we are in the "buying cycle" (like your "high value" customer who is in a trial period) we don't mind a polite, knowledgeable sales person helping us through the process. Your advice allows for such a polite, knowledgeable process. Thanks for the practical advice.

posted on Friday, August 27, 2010 at 9:13 PM by Desmond Pieri

Great summary of many useful tips.

posted on Monday, August 30, 2010 at 10:18 AM by John at RightOn Inventory Order Management

Very interesting article! I'm starting a digg competitor tech limelight that organizes content around products instead of categories. The traditional sales model does not really apply to my company at this stage. Does anyone have experience getting initial users for a content based site? It's a classic chicken and egg problem, but I haven't been able to find much useful information thus far. Thanks all!

posted on Thursday, September 09, 2010 at 5:16 PM by Marc MacLeod

Comments have been closed for this article.