Cody Bernard and Eric Holland are two awesome members of our product marketing team at °µºÚÍø.

And as product marketers, they’ve both been tasked with running win-loss analysis in-house during their careers.

No easy task.

They both have scars from this process. They both (barely) survived.

Now they’re sitting down to share their cautionary tales, and why they’ll never, ever do win-loss alone again.

Landing interviews takes oh, so much time

Eric Holland, Product Marketer at °µºÚÍø: 

At first glance, the win-loss process might seem straightforward: interview customers, gather data, and analyze. 

The reality? Well… not so much. 

When I first took on win-loss at a prior role, the lag time in just setting up interviews was nuts. 

It took roughly three months to get introductions from customer success, and another one to two months to schedule and conduct the interviews. 

The admin, the email follow ups, the calendar bookings, the rescheduling… It still gives me nightmares.

It was a part-time role in addition to my full-time product marketing job!

And by the time I could interview and collect insights, things started falling out of date. 

We’d be talking more about the customer’s ongoing experience rather than their initial decision-making process. They were in the honeymoon phase; totally different to how they’d talk and act right after purchase.

This delay led to outdated information that was less actionable and less reflective of the actual decision points that led to wins or losses during the sales cycle. 

I wasn’t getting the things my sales and marketing teams really wanted to know about.

Nailing an interview is a skill that needs developing

Cody Bernard, Director of Product Marketing:

The part of the process that I quickly appreciated when I first took on win-loss: interviewing is a learned skill.

You don’t walk into a conversation with a buyer and get immediately greeted with insight after insight on your sales process or pricing model or how that one ad on the Subway home caused them to buy.

It takes skill on the interviewer’s side to create a free-flowing conversation, while getting to the areas of focus that matter most.

But that is easier said than done.

When I took on win-loss in-house I was given a strict rubric of questions. And there was little room to deviate from the script.

I asked a question, got a response. Onto the next question. Rinse and repeat.

I felt like a teacher reading out attendance sometimes. 

But I got why they worked that way – I was a junior product marketer learning the ropes. I wasn’t an expert at extracting insights from a buyer. 

But rattling off of my script isn’t getting it done either.

It wasn’t until a full cohort of interviews that I even started feeling comfortable running a strong win-loss interview that could get beneath the surface. 


Want easier access to high-quality insights from your buyers? °µºÚÍø Win-Loss can help.


It’s impossible to check your bias at the door

Eric Holland, Product Marketer at °µºÚÍø: 

I was passionate about my company. And ironically, it made getting genuine insights interviews really tough.

My personal investment in the product led to inherent biases that inadvertently colored the interviews. 

No. Matter. How. Hard. I. Tried.

For example, I remember a specific instance where my enthusiasm for a positive comment visibly shifted the tone of the conversation. 

(In case you don’t know I’m an expressive person, and the moment they mentioned a newly launched feature that I loved… let’s say I perked right up)

The person on the other end could feel me nodding and smiling immediately.

I could feel myself steering the interviewee towards more praise rather than critical, constructive feedback. 

This emotional investment skewed the conversations, leading me down a path of confirmation bias rather than objective truth, making it challenging to draw accurate conclusions from the interviews.

Analyzing the data required an abacus (and an extra 10 hours)

Cody Bernard, Director of Product Marketing:

After I’d conducted interviews, then came the really tough stuff.

To this day, analyzing insights gathered from interviews was the most onerous and time-consuming process I’ve had to take on as a product marketer.

I would analyze the results in a Google sheet, putting all the questions along the columns and some account details across the rows.

Then I would manually enter responses into each cell. This would involve noting down the category of the questions (pricing, sales experience, etc) and then the sentiment of the response.

By the end I’d have a tl;dr bullet list for each question.

It took forever. I can’t even recall how many hours I spent on this; I’ve tried to block it out.

And we’re not even halfway yet.

The next step would be to create themes from these bullet lists. I’d need to put together a clear description of what is taking place to leadership – that requires going back into calls and pulling quotes from buyers for social proof.

This entire process would take so long that by the time I could share results, it was an out-of-date point in time. 

Product gaps that I’d identify would’ve already been filled. Functionality that was tipping deals had just been realized.

I was in a continual state of catch-up, digging up valuable insights, but just a little too late. 

(Psst, if you survived this and are now getting ready to present win-loss findings to your execs, save yourself some time our win-loss presentation template here.)

Get win-loss insights, without breaking a sweat

Cody and Eric each sunk hours of time into scheduling follow-ups, long interviews, and manual analysis of their win-loss program.

But they did this because they knew that the insights from their buyers are some of the most valuable for the business.

Thankfully, you don’t have to lose those hours. Because there’s now a smarter way to do win-loss.

Our AI and in-house experts at °µºÚÍø allow you to easily collect deep buyer insights at scale, analyzing key themes that you can bring to inform your executive leadership and enable go-to-market teams.

Learn more about °µºÚÍø Win-Loss here.