#HowIBuy – I’m a Software CTO, and this is how I buy.

 In #HowIBuy

Originally published on LinkedIn https://www.linkedin.com/pulse/im-software-cto-how-i-buy-steve-woods/

As co-founder of a startup focused on helping teams sell, I talk a lot about sales and selling. In a lot of conversations, that eventually leads to the question of “okay, but how exactly do YOU buy?”.

It’s a great question, albeit a tricky one. The truth is, at Nudge, I spend a lot of money on (mainly) technology and software. However, how I buy is nothing like how many organizations are trying to sell to me. As I tried to describe how I buy, many times I had to fight the temptation to describe something that would be more familiar, even though it was not true.

That helps no one, so although this may be a bit uncomfortable to some sales teams, here is my best articulation of how I buy:

Trust my Experts: First and foremost, the majority of the decision is made on the front lines. At Nudge we have worked hard to hire an amazing team of deeply knowledgeable experts, and the last thing I’m going to do is try to “out-expert” them. They know their areas far better than I do, so my involvement is mainly around prioritization of spend, non-technology alternatives (can we think about the problem in a completely different way), poorly considered ramifications (will this affect a team or a process in a way we might not have thought through), and sizing (are we looking to spend more than the problem is worth).

Proof is Reality: We buy nothing without trying it first. That’s not a philosophy or a stance, we just don’t. I’ve looked. So proof of how good something is is purely driven by reality. Case studies are not reality. Demo systems are not reality. Videos are not reality.

Everything is a Nuance: Every situation is different. Our data, processes, use cases, hardware, etc, are all unique. Not overly so, we try to do “standard” things as much as possible, but there will always be something that is unique to us that affects our success with a service. This means that we don’t buy until we’ve been hands on, in our environment, with our data and processes.

Education is DEEP: When two or three options are brought toe-to-toe, the comparisons are deep and data oriented. Often that means learning how to run a system at a level of speed, scale, or complexity that is representative. The education resources that the team uses will be at that level of depth. Videos of track sessions at highly technical conferences, Git repositories, test data sets, etc. These resources probably don’t have the volume of views and clicks that other marketing resources do, but they need to be present.

Litmus Test with my Network: I have never asked a salesperson for a reference. I’m not sure why I would, as I know they will select one of the most glowing, perfect examples. However, it takes 30 seconds for me to drop a question into one of the CTO forums or Slack channels that I’m part of, and get a short paragraph of perspective from two or three CTOs I trust.

Positioning is Relative: None of the solutions that we bought were simply deemed “best”. All the positioning and comparisons were along the lines of “good if you need X, less good if you need Y”, or “strong if you are in situation A, weak in situation B”. This can be on any set of dimensions; price, scale, configurability, etc.

Timing is Everything: There is a LOT of stuff our team could do. What we choose to do next is driven by many, many competing factors. There are many projects, solutions, and ideas that are on the “list” but that doesn’t mean we’re getting to them right away.

Free is Addictive: We have bought more than a few services that were free up to a certain generous usage tier. We went in knowing that it would get embedded, we’d get hooked, and we’d end up paying significant amounts for it down the road. It still happened.

People are Relationships: When people at a vendor have featured in the process, it’s about the relationship we have with them or that they bring to the table. Great service people have boosted a solution’s perceived level of support. Great sales people have introduced us to experts in the community on a technical topic, often not at their own firms. These efforts all matter a great deal.


So, if my situation is representative of the current reality of selling technology to CTOs, how does one sell into that reality?

  1. First, think through the overall buying experience, especially the parts that do NOT involve salespeople.
  2. Second, make education available. Deep, technical, and highly specific. It might not be high in views and clicks, but it’s powerful.
  3. Third, understand and embrace your position. You’re great at X, but not at Y. Don’t try to pretend to be great at X and Y.
  4. Fourth, focus your sales efforts on what you can provide. Additional resources a buyer might not have seen, data repositories, technical tools, tests for running actual comparisons.
  5. Fifth, think of your network as being a big part of your core value as a salesperson. What access can you provide to experts in the network, within your team, etc.
  6. Sixth, build an amazing product. More than ever before, the reputation of a great product becomes known on its own merits.

Glad to answer any questions on what does or does not work if I’ve missed anything. Good luck, and happy selling!


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Experienced SaaS CTO. Founded and guided the building of Eloqua to a market leading position in Marketing Automation. Now Co-founder and CTO at Nudge. Author of the book “Digital Body Language" with a passion for innovation, cloud computing and software evolution.
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