Interview with Tom Chiles from Vendavo

1. Stakeholders are more concerned with cost, speed, risks, and margins, as opposed to tech upgrades. And convincing them to invest in a back-end feature users might never “see” will demand a great deal of effort. What role does observability play in threading technical signals to business outcomes, and getting that organizational buy-in?

It’s a very good question.

In the age of AI development where vibe coding fast on localhost is easy, but getting things to production at scale is in my opinion where things always get tricky. Non-functionals and selling to IT as a secondary buyer has never been more crucial for enterprise B2B software deals.

Quantifying user drop-offs and having proper distributed tracing is a key part of making sure that system performance can be proven, and when you’re running a pricing system that runs some of the biggest manufacturers and distributors across the world, that can be just as important as the latest agentic AI feature release.

2. AI/ML-driven pricing logic has proven to be a black box for enterprise buyers. And, very specifically, internal stakeholders across finance, security, and RevOps demand more transparency into why a system suggested a specific pricing margin. Can you help product leaders understand how they can define and layer cross-functional governance without inciting chaos into workflows?

I think one of the main misconceptions about AI and machine learning pricing is that it’s all or nothing, there are many different methods available to people today.

Vendavo for example offers different options based on the organization’s maturity: price rules are always traditionally a jumping off point for B2B pricing teams, we now offer also machine learning recommended price rules, and fully fledged machine learning deal optimization.

All of these options have detailed auditability, but heuristic rules-based pricing is still the most transparent but can actually be augmented in terms of how they are created, as well as maintained, with machine learning.

Governance is the other key angle, and this is where established price management functionality is key, having clear information on why a price is being changed, and scheduled to be changed at a specific date (and other standard price change operations like this) are table stakes in the world of B2B pricing, but are incredibly crucial to ensure augmented or automated pricing processes are really going to be deployed and used across a large multi-national businesses.

3. As the Director of Product Management at Vendavo, you’re tasked with managing a diverse tech portfolio of overlapping or adjacent solutions- which, without clear positioning, can lead to sales friction and buyer confusion. Given that you’ve successfully launched major complex releases on time, do you have a blueprint or playbook that has helped you diagnose such an overlap and avoid portfolio cannibalization?

Identifying the gap is always going to come down to use cases, and are they tackled in a different way, and is it for a good reason.

A lot of the time in pricing especially, there is definitely an answer for the “good reason”, I would love it if every customer had an identical pricing process, but they are highly nuanced in every single large B2B business in the world. When there is not a good reason and it is actually cross over and we are duplicating development and maintenance effort, it is up to the product management team to be ruthless in stopping this at source and adjusting plans.

Avoiding portfolio cannibalization is always around collaborating with the best team equipped to make sure the company and customers clearly understand and rally around the product strategy.

Product marketing is key to ensure that there is clear sales and customer education on ideal solution fit for the right business, subvertical and profile. Once you define with specificity the target markets and nuance of each, these trickle down into buyer personas, user personas, problems you are prioritizing and ultimately removing the overlap from what you are shipping at the point of release.

4. Enterprise pricing managers manage billions in revenue with the help of legacy systems and muscle memory they’ve developed over the years. Even the slightest UI redesign in this case can feel risky or disruptive. In your opinion, is it really possible to map a controlled redesign- and help managers navigate their operational inertia?

Absolutely it’s possible, it’s definitely not easy in practice.

We come across a lot of pricing teams who don’t love their current workflows and excel based life, but getting users to really want to change their processes takes time, and proving that what you are offering isn’t just a shiny new product.

You have to prove that you are making their lives easier, giving hours back to their team by removing administration, and opening up use cases they didn’t think available to them across the pricing waterfall.

5. Accountability of multi-million ARR products means making hard trade-offs between technical debt reduction, platform stability, new feature velocity, and M&A integration. In such a case, what has been your praxis for allocating engineering bandwidth across multiple development teams to protect the baseline P&L?

That’s a really good question, and it’s definitely an area that does keep me up at night.

It always requires beginning with the company strategy and working with the executive team to align your product strategy to it. Once you have aligned goals that are clear and trackable, major product investment decisions absolutely must move the needle toward the company goals.

A company focusing slightly more on new logo will probably over-prioritize new feature velocity, where as an organization that is retention focused will lean more toward platform stability and technical debt.

There is unfortunately no rule of appropriate % split and is always changing and nuanced to the company. I would just say as a rule, company and portfolio goals should be set and reviewed yearly, and you should review your plan around these at least quarterly on your big bets and allocations in product development.

6. Owing to your experience in leading technical product managers (TPMs) at Vendavo, you must constantly oscillate between deep-in-the-weeds engineer speak and communicating with internal stakeholders. How have you coached TPMs to present high-level value propositions in QBRs that don’t end at API specs- without, of course, overwhelming them?

Having a product manager that is strong in all areas naturally is really rare and takes a lot of time. I am still working on areas to improve every day and I think that’s one of the most important things in a technical product manager role, growth mindset, always wanting to learn is the most important thing.

You will always be the jack of all trades but master on none, but you have to bring it all together.

Technical product manager can often come from a technical background like myself, and the QBRs, presentations and more business parts of the role definitely took time and focus.

Two key things I’ve learned is: present as often as possible and say yes, this is by far the best way to get yourself comfortable, and for technical people too in the detail during presentations, setting prep sessions to pitch with a clear short meeting time (for example 5 minutes), gets people quickly used to talking clearly and getting key points across without diving into technical detail.