FinTech at scale requires great products and services, market intelligence, and a high sales win rate.  Analyzing the reasons for won and lost deals in a competitive market is therefore crucial.  Lacking that information, innovation is intermittent at best.  Companies that scale, and survive long term, continually innovate – in their products, technology, business models, and sales methods.  Rigorous win/loss analysis is a structured way for salespeople, sales managers, marketers, and product managers to understand their competitive position, unmet market needs, and buyers’ behavior.

“When there is no technological advancement, companies tend to ossify. They’ll keep doing what they’ve always done because it’s worked, except now it doesn’t work…” [Video

Teams of general practitioners and domain experts are needed to systematically perform a data-driven, actionable investigation program in a unique vertical market.  The following interview series presents discussions between Richard Case and Dan Hubscher on topics affecting win/loss analysis in sales of financial technology.  These topics include what is win/loss analysis, who is it for, why is FinTech different, and how to run an effective analysis program in that market.

Richard H. Case, Principal, founded PSP Enterprises to directly address the shortfalls in the win/loss analysis industry.  He has over 30 years of win/loss experience, and has advised many of the largest high tech software and hardware companies in the world.  By using IT professionals and leveraging his own decades of knowledge, Richard has redefined market research in a way that leads to direct, actionable results.

Dan Hubscher, founder of Changing Market Strategies, is a stakeholder analyst and agent for quant funds and FinTech companies.  He has over 20 years of deep subject-matter expertise in quantitative investing and electronic trading technologies across cash and derivatives markets, market structure, regulation, and industry advocacy.

PSP Enterprises has partnered with Changing Market Strategies, specifically to provide FinTech specialized, peer-level, confidential interviews, and to deliver PSP’s patented analysis services, to vendors serving the financial services industry.

Richard:  Dan, Why don’t we get started with a definition.  How would you describe win/loss analysis in Fintech?

Dan:  Sure.  A simple definition of win/loss analysis is that it’s about gathering insights directly from buyers into competitive sales deals that companies win or lose.  This way, companies can understand why prospects make the decisions that they do.  And then the companies can take the actions needed to improve future sales outcomes.

Some people look at a win/loss exercise as some kind of “secret shopper” program, something you could hire a relatively inexperienced, robotic interviewer with a script to do.  But, it’s not what you might imagine.  Getting to the truth, and harvesting actionable insights from that truth, takes trust. You need expertise, confidentiality, and strong analytical methods.  Basically, you need to be from the Street to talk to people from the Street, to really extract what they’re thinking from the conversation.

Therefore, one of the questions that we will need to dig into together is, how does win/loss analysis work differently in FinTech vs. other industries?

Richard:  Yes.  But to do that, you need to understand the background of how this works in any industry.  We can start to answer that question by examining the lessons I learned from 30 years at the “front”.  Such as, why not just ask your sales team why they won or lost, why do you need senior interviewers, why do you need anonymous interviews, and how to avoid the mistakes that are common to win/loss analysis.

Dan:  Yes. And then we can look at some unique FinTech perspectives:  how the build vs. buy decision is different, why the reasons you win aren’t the same as the reasons you lose, and why it’s so much more difficult to uncover the truth where profitable trading is at stake.

Richard:  And finally, we have to look at the bottom line: how do you build actionable analytics into a program.  How do you answer the great “What if’s” of product and service development.  How do you measure the prospective impact of future changes.  And why you need to win both hearts and minds in order to win the numbers game.

Dan:  I think quants would appreciate analytics based on a lot of data. But the narrative that speaks to hearts and minds is something everyone can relate to.  I think that just like financial markets have their boom and bust cycles, FinTech itself has its own boom and bust cycles.  I’d say we’re at the beginning of another technological boom cycle in automated trading and investing right now.  But that’s hot off the heels of a long period of little innovation, and it might not be long before we’re back there again.  If I’m right, why would you need to understand the intricacies of why you win and lose, now, in the current market?

Richard:    Because when there is no technological advancement, companies tend to ossify. They’ll keep doing what they’ve always done because it’s worked, except then it doesn’t work.

Dan:  Yes, indeed.  I  think we’ve all been there.  So let’s dig in…

… So, watch this space, as Richard and Dan tackle these win/loss analysis issues.  You can always get more depth on the issues, and the history of how the lessons were learned, at  Or for more on win/loss in FinTech, visit