How to land a big fish

Startups often want to sign up well recognized brands as customers. It increases the credibility of their own brand and provides social proof to their smaller customers.

However, the sales approach that worked for a smaller customer doesn’t always work for a larger one. This post details a situation where I failed to recognize the difference in approaches and some tips to avoid similar missteps. I find myself drawing upon these lessons every day at Filestack.

Before Filestack I was at Wipro for about 7 years where we went from being a small company to a $6bn corporation. During this period, I met Richard, an engineering lead at a prospective customer. We met at a conference and we spoke about his work, my product and we seemed to generally connect. I knew that our product was awesome and provided tangible performance benefits for his project. To follow up, I offered him additional information on our offerings, answered his technical questions, and shared case studies of other customers.

We went back and forth for a couple of weeks and then the trail went cold. It seemed like we were making progress on working together but somehow the conversation never progressed to a point where Richard wanted try us out. So, I mustered courage and asked Richard out for a drink to figure out where he was in the decision making process.

As we chatted, I learned that one of our larger competitors had already started a proof of concept with them the previous week. But how could they beat me to the punch? I had a more cost effective & technically superior solution. I had managed to convey (or I thought I did!) these benefits to the engineering lead who was responsible for implementing it.

Well it turns out that Richard was not the only person in the buying process and our competitor had effectively tapped other stakeholders to engage them in the buying process.

Lesson 1: In larger organizations there are multiple individuals with separate motivations involved in the buying process

In this case, the competitor had mapped out and addressed the motivations of each of the individuals below:

  • VP of product: He was interested in whether the product helped achieve business goals-user engagement, adoption?
  • VP of engineering: He was interested in whether the product was easy to integrate and maintain? Was it easier & cheaper to build it in-house instead of buying it?
  • Front-end engineering lead (UX): He was concerned if the product would screw up his UX?
  • Back-end engineering lead: He was concerned if the implementation was scalable and met performance requirements?
  • Principal security engineer: He was concerned if the product would add security holes?

I realized that it is important to map the various people in the prospect organization and understand what their individual motivations are. Once I mapped them I would need to tweak my product messaging to address the needs of each of these stakeholders.

Lesson 2: Your buyer is very busy. Help them help you.

One of the things that Richard mentioned was that it would take him a lot of time and effort to bring all the stakeholder on the same page, get their inputs on the choices and build consensus on the right product to pick. And Richard was busy; he was a part of 3 scrum teams at the same time.

The competitor had done all this work by going around the organization, interviewing the stakeholders, putting together presentations and data dockets that addressed their needs. This was work that Richard would have had to do otherwise. Thus, the competitor had helped Richard help him!

You will notice in the example that it must have taken the competitor a lot of time and effort to do this. Be ready to invest that time and effort if your aspirations are to sign on a larger customer.

If you are ready for it, then the next question is what are the key questions that you can ask to map the stakeholders and their motivations? Here are some examples of questions I wish I had asked Richard.

  • “How will you take the decision on which projects to invest time in?”
  • “What is the definition of success for this project and who else will be positively impacted if the project succeeds?”
  • “Who are the other individuals in your organization that you suggest I meet?”

In summary, in larger organizations there are multiple individuals with separate motivations involved in the buying process. Help your contact by doing all the leg work for him that he would have to do otherwise. Yes it is a lot of work but signing a recognized customer increases the credibility of your brand by providing social proof to your smaller customers.

And if you’re really interested in evangelizing a technical product to customers, let us know, we’re hiring.

Find out more about what we do at, and Discuss on HN.

-Anand Dass

Read More →