[Interview] How ‘Jump’ learned by selling
Parker Ence’s unfolding story
Parker Ence and I have pretty similar stories. We’re both MBAs (him Stanford, me Harvard). We’re both overthinkers. And we both have spent 12+ months in the pre-product-market fit pain cave.
I want to share Parker’s story as a co-founder at Jump, in part because I’m a huge fan of Parker and the business. But more importantly, Jump’s path to product-market fit is a great way to show the difference between two startup worldviews - the planning model vs. the unfolding model:
1. The planning model
Start with hypotheses and assumptions, perhaps a business model canvas if you’re feeling spicy
Do tons of customer discovery interviews
Create spreadsheets with your “riskiest” assumptions
Run experiments to “validate” product-market fit, “scientifically”
Build your minimum viable product with design partners
Nail it, then scale it
2. The unfolding model
Try to sell, using a case study to try to replicate a case study
Debug the case study to make selling & delivering easier
See what unfolds
You know where I stand: I believe the “planning” model is a mind virus; it’s the #1 killer of startups, innovation, and economic growth; it neither makes sense in theory or in practice.
So if you’re stuck in experimentation / research / discovery / pre-PMF purgatory… or you’ve banged your head against the wall trying to follow the “scientific” planning approaches… read this closely!
If you enjoy these interviews, you’ll definitely enjoy my next founder-led sales accelerator, where I’ll help you figure out your business by selling. You’ll emerge with an end-to-end founder-led sales process that you can iterate to product-market fit.
Learn more about the program here, and fill out this brief form to apply.
If you want to dig deeper into the unfolding process, check out these two newsletters (1, 2).
This interview has been edited for brevity and clarity.
For context, here’s what Jump does today:
“Wealth advisors used to take notes manually. Now they use Jump — the only way to turn conversations into tasks, notes, and compliance records with secure AI.” Jump is essentially tackling all of the admin slog that financial advisors have to deal with before and after their client meetings with some new applications of GenAI.
I love how open Parker is about his winding path to product market fit. As you read through this, how many of these things have you tried with your startup?
The reason that I originally signed up for Rob’s program was because when Rob would post about overthinking everything and running all the experiments and banging your head against the wall, that resonated.
Here’s our story: The first version of this company was basically us sitting in a room and thinking very hard. We had this massive spreadsheet of different ideas, and used a formula to tell us which idea was the best.
When we found our winning idea, we then came up with a list of assumptions and experiments and force-ranked hypotheses for what we needed to validate, in which order.
At this point, Jump’s winning idea was in the fintech space. After investing time in your typical validation exercises, Parker and his cofounders went to a conference, “and nobody cared.”
The Jump team then followed another pretty common advice point: “solve your own problem”, which led to a pivot into AI sales tech. They decided they were going to be even more rigorous about “doing it right” this time. Here’s how Parker describes that process:
So of course, we tried to do this by the book, and did about 100 customer interviews and had a beautiful spreadsheet where I was tracking everything. I even had interviewees force rank their pain points on a scale of 1-10, and then we did a lot of very scientific analysis and the math told us which pain point to focus on.
All these sales reps said that the most hated, “10 out of 10” pain point was updating Salesforce after sales calls. If you talk to any rep they will tell you they hate updating Salesforce and it totally made sense, we’d experienced that ourselves in past companies.So we leaned into that, built a design partner deck about our vision for this product. Everything made sense on paper, and everyone we talked to seemed very excited about it. We closed with a “design partner” pitch, where we’d get sales AEs or VPs of sales to co-develop the product with us in exchange for using it for free at first.
We worked alongside our design partners as we built the product for 9 months. We honestly built a lot of very cool software. And the initial feedback on the product from users was glowing.
Then we finally went and asked for money. And they were either like, “Oh, now that we think about it, we sort of have this other software for this, I don’t think this makes sense for us, but LOVE what you guys are doing.” Or, “our willingness to pay is maybe a max of $5 per user per month.” Or they’d name a competitor.
After all of that work, after all of that validation… it felt like we were back to square one. This was very frustrating.
(I have heard a version of this story ~150 times.)
Asking for peoples’ opinions without selling just doesn’t work. In Jump’s case, entering data into Salesforce is, I’m sure, annoying. It’s a pain point. But is it a business? People have a lot of pain, but they live with that pain.
There’s only one way to find out: By trying to sell. You can waste a lot of time - years, decades - doing everything but selling. Sell to learn, sell to get real.
Here’s where Jump’s story gets interesting. Parker had a chance conversation with a neighbor who was a financial advisor about what he was building. The neighbor ran a successful financial advisory firm and asked to use Jump’s product. Parker figured why not. Jump’s team set up his the financial advisory team with access along with a lot of disclaimers about how the product was not really intended for their use case.
That turned into more conversations and mutual excitement and an increasing amount of time spent with more financial advisors who were much more excited than Jump’s prior market.
This is how businesses unfold. Random, unpredictable anomalies hint at demand. The founder recognizes a strong “hell yes” signal (usually in the form of an enthusiastic purchase), then doubles down on redesigning their business for that specific customer and replicating that specific case study over and over, to the delight of real customers paying real money.
More conversations and product adjustments followed, and soon Jump was only working with financial advisors, still with the “design partner” structure.
At this point, Parker and the Jump team joined Cohort 2 of my program. My product-market fit methodology is simple: Sell to learn. Most learning happens when you hear, “no.” Here’s how Parker describes that experience:
I realized that it was time to actually sell, no amount of additional R&D was going to get us where we needed to go. The first time I gave a real proposal to a wealth advisor, I completely offended one of our favorite design partners because we asked for way too much.
Up to this point, they’d been giving glowing feedback to us. But what I realized was we asked for money, we finally got the real feedback. He basically said, “Look, it would make no sense for us to pay this much right now because of this and this and this and this.”
So that became our next product sprint.
And at the same time, we reorganized our sales deck based largely on many of Rob’s recommendations around how to put our pitch in the context of a case study and structure the slides to optimize for learning.
(Shameless plug: Startups that join my program get my to-the-point sales deck template that we develop together, use in real sales calls, and debug. That’s what Parker is referring to. OK, back to Parker.)
So towards the end of Rob’s bootcamp, we had iterated on our sales pitch a few times and were asking for money. I still remember the first time I met with someone who came in through LinkedIn. I ran through the messaging, and he signed up at the end of the call. It was our first paying customer that had no personal connection with us. This was a huge turning point for us.
These first sales are always messy. They’re often slow. They’re usually awkward. But you quickly learn and improve, so the next sale is easier and smoother and less painful.
Since joining the program earlier this year, Jump has quickly scaled to hundreds of customers. Even though they’d originally intended to bootstrap, the demand signal was strong enough that they went on to raise $4.6m in venture capital from great investors. They’re getting industry innovation awards, customer referrals, and attention from some of the most influential buyers in their market. I have no doubt they’re going to be a massive success, and I’m just glad to see good people win.
My favorite quote from Jump’s story:
During sales calls, our prospects now generally nod along and often say things like, “Wait, are you a financial advisor?” or “It feels like you’ve been sitting in on our internal meetings.”
This is the power of messaging refined by the ‘sell to learn’ unfolding process combined with a dedication to early 1:1 sales conversations.
Parting words from Parker:
If I was starting all over again, after getting to that initial spark of an idea and talking to maybe 20-30 potential customers to get the lay of the land, I’d put together a few slides and start selling something deliverable.
Here’s why I think “sell to learn” makes so much sense. If you are not asking for real money, then what you are doing is a “social” transaction. Our brain behaves in a very different way when we are in a social transaction. We are more generous, positive, encouraging, less discerning even. But when money is on the line, that’s an “economic” transaction - the other side of our brain lights up and we start actually evaluating if there’s enough value add and urgency to buy something now. The thinking is completely different.
For clarity, I’m not talking about “running experiments” where you simulate asking for money, like some landing page where you ask for a credit card as a test and then don’t actually charge the buyer or send them a product. That doesn’t go far enough. We needed to actually deliver something to a real buyer to see if they were still happy. That’s what closes out the feedback loop.
Of course this is not a magic bullet, you still need good insights and a great team and to eventually unfold your way to real demand. But of everything I’ve tried (this is my 4th tech company, I think I’ve tried everything), I believe that “sell to learn” is the worst way to find 0 to 1 PMF other than all of the other ways :)
It should be every founder’s aspiration to so deeply understand and serve customers that they feel like you’re speaking to their souls, like no other company has ever done. For Jump, this happened in a gradual unfolding process. Selling to learn. Getting into the arena with something. Iterating messaging. Being open to where the demand actually was. No shortcuts. I don’t believe it’s possible any other way. It certainly can’t be planned or validated in advance.
Parker loves to chat about this stuff, so feel free to connect with him on Linkedin: linkedin.com/in/parkerence