Rolling not round: A product management mindset from Vendasta’s Gib Olander

Vendasta is an ecosystem with three primary users joined together to form a marketplace for transactions. We serve three independent but connected user types who share the need to solve friction for six use cases: build, market, sell, bill, fulfill, and deliver. At Vendasta our three user types are channel partners, vendors and the small and medium businesses (SMBs) they and we serve. We also bring together those use cases, offering an end-to-end solution or operating system for our users.

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Fundamentally these use cases and users come together to help local economies thrive by democratizing technology. Helping channel partners, vendors, and SMBs find new people to buy the products they offer is at the heart of what we do at Vendasta. Additionally we help them find additional products or services to sell to the people they already know, driving local transactions. 

In this complex environment you can’t follow the typical product management theories of narrow focus. You can’t rely on the adage that the most important power for a product manager is saying “no”. 

Most product management advice you read in a textbook, substack or tweet thread was written from experience in a previous mindset. That mindset was formed when raising seed capital was hard, during a time when standing up a tech stack took serious time and capital. The classic refrain in that era was to have a super narrow focus, deliver features and obsessively hone in on a specific user and customer segment. This approach has been very successful and led to an explosion in the SaaS industry,  which has increased in size by around 500 percent over the past seven years. 

With this explosion we have a new competitive landscape. Our users have new problems to solve which means we have to evolve our product management philosophies to keep up.  

In the previous era finding a point solution to solve a problem felt much like discovering that crumpled up $10 bill in your winter coat. You know, that one from last winter you only discovered when you dug your coat out again for the first snow? A feeling of pure delight. 

Today, the expectations have changed. The typical software purchaser's expectations have changed. Just like how our expectations of Google have changed over the last 20 years. 

In the early days of Google search, getting a search result with 10 blue links felt satisfying, we would cobble together an answer from those disjointed but relevant choices. Today the expectation is that Google will give me a perfect single answer to my question. People don’t want to buy 10 independent software solutions, they want a platform or operating system that empowers them to grow their business.

Today an organization that makes an investment in a SaaS product is expecting it to solve an important job to be done (JTBD). To meet this evolving market desire, it means Vendasta must build software that offers solutions to the interoperability of our partners six primary use cases: 

• Build
• Market
• Sell
• Bill
• Fulfill
• Deliver

This should be achieved while also allowing our three cohorts of users to interact with each other, generating efficient transactions and seamless multi-party threaded communication.  

To do this Vendasta needs to think and behave more like what Ripplings founder Parker Conrad calls a “Compound Startup”. 

This change in the landscape means we need to take an evolved approach to product management. One where we build off shared services. Where we build for the widest possible audience, thinking about integrations. We must identify when we can be a system of record and when we can be a system of engagement but we never give up both.  We must build for the interoperability of software to complete an end-to-end experience for our customers and their customers. We must focus on maximizing the ability to bundle, and price accordingly to take advantage of this. We need to maximize the advantages of strengthening the shift left approach in DevOps.

In ushering this evolution in product management, I find myself using a favorite old saying “rolling not round.” I absconded with this phrase when a mentor said it to me many years ago. “Gib, get it rolling, cause if it rolls long enough it will eventually be round.”  

This rolling not round thinking allows us to start with a generic problem to be solved. We can think about the widest possible audience. We can focus on the result that our ecosystem needs to achieve and drive an outcome for our partners, their customers and Vendasta. We know that this first slice will offer us a Lodestone into our partners workflows and processes. Once we have this initial compass into how our partners use our software, we can roll the product to break off the rough edges in a commercially viable way, we can use efficient prioritization to tackle a wide set of problems instead of trying to solve all the specific needs with our first slice. This allows us to tackle more problems, provide more value and expand the bundle.   

Once we get this compass in place and our stone starts rolling, we get to learn which other software needs to work with our solutions leading to new product ideas or integrations. We learn why that software is important, which parts of an organization need access or a slightly different configuration. We learn what features are critical to solving the job to be done. We can see the optimized interoperability needs of various software components, as well as what types of data need to be orchestrated. All of this learning is done with real, invested users. We get the ability to use metrics and measurements to drive outcomes, not just deliver the next output of a feature. 

Rolling not round is a mindset. A product is never finished and in today's world having the most bells and whistles is important when a product gets evaluated independently. When a product gets evaluated in the context of an end-to-end business process, however, it’s not the product with the most features that will win.  It’s the seamless integration of the right features to help your user win.  

So at Vendasta we put the adage rolling not round to work by trying to find a core use case that fits squarely between our three user types. We then define a job to be done. We quickly provide value to the widest possible audience in our first slice, then adding features, functionality and configurations in each subsequent revolution making the product rounder and rounder each and every sprint which grows the product faster and faster. 

It’s funny how words like rolling not round can rattle along in your head and change nearly everything you do, but not even register with the person who said them. In this case years later, I thanked this mentor for the sage advice. He smiled and said he didn’t recall saying it. He left me saying “it looks like you’ve put it to good use, so you can say it’s yours.”