How to Sell Me Your Technical Product

Tips from someone who buys a lot of SaaS/IaaS/YaaS stuff

Ask any CTO about their experiences with technical sales, and after they suppress the throat-vomit, they’ll begin by telling you of the cold emails and cold calls and cold 6-megawatt-spark-plug mailers. Just this past week, I’ve received ice-cold pitches for dozens of SaaS products with such instant-delete subject lines as:

• Fwd: Intros
• Appropriate person?
• Intro: Matt <> Sales Dude (SomeBullshitCo)
• RE: are you available this Friday?
• Re: Matt, post-lunch 20 minutes
• RE: Re: Final call, Matt
• I am doing my best and trying to break the code to your silence 😃

Yikes.

Cold emails are the lowest-leverage sales activity imaginable. If cold emails are the way I first come to know about your product, you’ve really misallocated resources. If you’ve got your priorities so wrong in sales, I can only imagine how much worse they are in your actual product.

We’re slowly heading toward a world in which all software is sold directly to the consumer, in this case the developer. The moat around enterprise-sales-focused companies is drying up rapidly. Cold emails to CTOs will get you nowhere when businesses go the serverless, service-assembly route. Only tactics targeting large numbers of individual developers will move the needle.

If you’re a SaaS, infrastructure, or tools company, here are some future-proof, high-leverage ways to get my attention and turn me into a paying customer:

• Tell the story from my perspective. Evaluating a new tool is a huge personal and organizational cost. In a matter of seconds, I weigh that “trial cost” against the current cost of the problem your product purports to solve. To overcome the powerful effects of status quo bias, you have to convey in that tiny window why you’re 10x better than what we’re doing now. Buddybuild did this brilliantly, telling me we could throw away a rat’s nest of shell scripts and half-baked services and instead deploy iOS apps to testers in zero clicks.
• Market with documentation. Your website can be totally bereft of high-production videos and still win me over as long as it gets to the docs quickly. Well-indexed, example-filled, hyperlink-saturated documentation is evidence that my team won’t have to struggle to use your tool. If you show docs only to paying customers, you’re effectively saying “trust me, it’s really easy to work with.” I don’t trust you. Twilio has long been the standout in this category.
• Inception by open source. Open-source your API clients. Better yet, contribute back to the FOSS projects that enable your business. Have your technical leaders speak at non-proprietary conferences. Open source is the ultimate inside sales: it gets my team to sell me on your product from within my own company. TravisCI has made itself the standard for continuous integration in open source GitHub projects, making it a no-brainer for us to test our own projects with them.
• Hire engineers who blog. This is different than making your engineers blog. That engineers and leaders on your team are able to articulate technical problems in writing is a strong indicator that you design products from my perspective. Opsee is a young company with already impressive output.
• Don’t spray and pray. Download my app. Look at my LinkedIn. See if I’ve bought or worked with your product in a previous role. I’ll always respond to a thoughtful email from a company that actually relates to our needs. Of the 100+ I receive a month, maybe 3–4actually show signs of having done homework. (I don’t blame salespeople for sending me crappy emails, I blame their management for not training the difference between building relationships with humans and spamming.)
• Price transparently. I understand that things get more complicated for massive customers who demand stringent SLAs and the like, but there is no reason not to make pricing public for the 90% of your customers who won’t hit the upper tiers. If hiding your prices is how you compete, AWS is on the way to eating your lunch anyways.
• Let me try it. There’s a good argument for not having a “freemium” model, particularly if your product doesn’t have network effects. But you must offer something public and free that gives a substantial taste. If evaluation involves a webinar, an over-the-phone-walkthrough, or signing an NDA, forget it.
• Watch your language. The possessive in “I can have my engineer join the call” tells me you don’t care about the technical part of your business. Sexism immediately kills a sale. Hetero-presuming comments like “We’d love to send you and your girlfriend for a weekend upstate” make me wish bricks could be hurled via phone.

Bottom-up will be the only viable way to sell software in the near future. Start using these tactics now, and just stop it with the cold emails.

PS: If you’re in the early stages of developing a product that solves a developer problem, some of these tips might not yet apply to you. I always love fiddling with new tools—don’t hesitate to drop me a line.