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Started a company that sells SAAS to US investment banks. I was a former banker and spent a lot of time priming my colleagues for the service prior to starting it assuming they would be willing customers when it was ready (we addressed a niche that was quite a problem for the banks). I thought that if we built a better mouse trap that significantly improved the user experience (for investors, the under writers and the issuers - the companies that actually raise the money) and saved everyone thousands of dollars it would be a no brainier for the banks to use us. Didn't happen. When the time came, bankers who, contrary to public perception are highly risk averse and focus on risk mitigation, didn't want to migrate to something untested despite our domain knowledge and demonstrable improvements. They didn't say this of course - it was always another reason such as "it's not my choice" or whatever.

The way we established a foot hold was to go straight to the issuers. What made our service unique is that while a bank was our user the service was often chosen on behalf of someone else (their client, the issuer). 99% of the time the issuer is silent on which service the banks use, after all they pay the banks to advise them. So we instead sold the service to them (well in the beginning let them use it for free). They in turn told the banks that they needed to use our service and the banks, who ultimately serve the issuers, simply complied. Once we had 2-3 of the banks onboard, network effects kicked in. With each sale we would go to another bank and say "let me show you what we did for XYZ"

Moral of the story (for us at least): 1) someone may indicate they are a champion but when the time comes, most are unlikely to be there. For every team of 40-50 you can at best expect 1-2 people willing to be champions 2) if possible (and I can appreciate that not all services can do this) sell to the person that ultimately benefits from this. In our case, banks use our software in relation to capital markets deals for other companies like John Deere so go to John Deere directly. 3) random point not mentioned above but worth highlighting ... I find that enterprise customers care more about making a dollar than saving a dollar. Our sales improved dramatically by tweaking the message to focus on this. If possible, focus on how you help these organizations grow P&L 4) I am a HUGE believer in Trojan Horses (and I don't mean hacking software). If possible, figure out a way to get your prospects using or benefiting from your software immediately by giving some service away (maybe not even your core service) weekly or if possible daily. The more they interact with you, the easier it is to bridge the divide and get through the process. 5) last point, don't get hung up on engagement letters. I know the lawyers will advise against this but a lot of deals die in the engagement letter phase. I appreciate not every business can do this but I made it crystal clear to my accounts that if they don't like my service they don't need to pay for it - that gave gem the comfort to use it regularly and at the end, they all paid for every use.

I can go on further on some of the tactical nuances of the above and other strategies. Feel free to ping me.




Yeah I'd like to hear more. What are the specific ways you tweaked your message to focus on making a dollar?


In a typical enterprise sale, the people making the decision (to buy your solution) are usually too senior to be the ones actually using it. There is a subtle corollary to this that I did not appreciate at first... often, these people are responsible for the profit of their group but less responsible for the costs associated with the technology. Thus, teams are less sensitive to cost than they are top-line revenue. There is a lot of theory about how silly focusing on top line is instead of profit but we all know the difference between theory and practice.

So how did I change my pitch: I ripped out all the slides that walked through my site and all the neat ways we saved time, automated workflows, etc. I focused on the data we generated (in one page) and threw in two case studies that highlighted how decisions made with our data generated more revenue.

It is important to highlight that the pitch-deck is not what is selling your solution, you are. The key is to tell a story worth listening to and I use my pitch decks to guide that story. My pitch today has X pages:

- Cover Page - Page with client logos (demonstrating social acceptance) - Page with big picture showing our platform works on all browser enabled devices (a major innovation on wall street) - Page demonstrating the insights our data creates - 2x case studies

Hard to put an exact number on how well this new method of focusing on the outcome rather than the solution has helped but I do not believe I am exaggerating by saying it improved close rate by 1-2 order of magnitudes.

If you want to read some great books that I believe will dramatically improve your close rate, I recommend the following in order:

1) Dale Carnegie's How to Win Friends and Influence People - if put in practice, this will pay a life-time of dividends. I wish this was taught in schools.

2) Getting to Yes (on negotiation theory) - a powerful negotiation framework allows you to create and preserve value in very measurable ways.

3) the Psychology of Influence - great case studies on how people make decisions, often in ways that are irrational. I incorporated a lot of the learning points into my pitch and in our slides and absolutely saw a shift.

I love thinking through this stuff so to the extent you want to chat more, happy to hop on a call or grab a coffee if you're in NYC. Shoot me an email (in my profile).


Thanks, it's so useful to get this kind of detailed advice from someone who has worked through these challenges. I may take you up on that offer!




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