Roadrunner Rebuilds CPQ for AI-Driven Pricing Complexity

Key Quotes

"probably the number one thing that used to break my back was that the underlying software with like a salesforce cpq and others just to like create a quote get it approved is horrific like you think if you think you've seen bad software you haven't until you've seen a 30 second loading screen to get from one page to another when you're trying to close a deal with like two days left in the quarter"

Joubin Mirzadegan highlights the severe inefficiency and user frustration caused by legacy CPQ (Configure, Price, Quote) software in enterprise sales. He explains that these systems, designed for a simpler era, create significant delays and bottlenecks, particularly when sales teams are under pressure to close deals quickly. This personal experience with the pain points of existing software is a foundational element of his new venture.

"I think the the transition from the CRO to the founder whatever it happened like what episode 70 or 80 when I was like because it was only cros for a while the thing that I found refreshing I'm curious if if you've seen this is that founders and ceos have an authority to speak in a different way than somebody on the executive team where they can just talk and so much of what I want to do is have like an earnest and honest conversation and it's harder to do that when you're thinking what is my boss going to think whereas if you're the founder you can just speak you can just speak you know"

Joubin Mirzadegan discusses the shift in his podcast's interview strategy from Chief Revenue Officers (CROs) to founders and CEOs. He explains that founders often speak with more candor and authority, enabling more genuine and honest conversations. This allows Mirzadegan to explore topics more deeply, as founders are less constrained by internal hierarchies or the need to consider their superiors' opinions.

"What Windsurf got right was probably a couple of things the first was a commitment from the founders that they want to both build Google class product and Salesforce class distribution yes like it was a true commitment from the beginning okay and most founders okay a lot of founders will say the product will sell itself as long as we build a good enough product people will come they'll come they'll pay 30 a month exactly and then they'll just love us so much they'll do and magically upgrade exactly which usually doesn't work that way"

Joubin Mirzadegan emphasizes the critical importance of a dual commitment to both product excellence and robust distribution, using Windsurf as an example. He contrasts this with a common founder misconception that a superior product will automatically drive sales without a dedicated go-to-market strategy. Mirzadegan argues that this integrated approach, marrying strong product development with effective sales and distribution, is essential for significant growth.

"The problem is about to get way worse okay and so it was a problem that i kind of like was feeling because i was like oh the underlying data model is just breaking because 20 years ago salesforce cpq was not designed for like all of these permutations right it was like a static world where one person is a netflix license the most you could do is a family account right okay so that happened then i joined kp and um uh lauren on my team and i started a group of tech cios 35 tech cios okay companies like uber and box and others okay that meet twice a year and this was like four years ago so like pre llms pre anything uh i i asked them what is the number one problem that you have in your company right now so it was a dinner with like five cios and they were like uh cpq and i'm like no way and they were like no i'm not kidding you they said we are getting yelled at by our chief revenue officers and sales people all the time because the underlying software that we're delivering to them doesn't work"

Joubin Mirzadegan explains the thesis behind Roadrunner, focusing on the inadequacy of current CPQ software for modern business complexity. He details how pricing models have evolved from simple per-seat licenses to intricate consumption-based and bundled structures, overwhelming legacy systems. Mirzadegan recounts how discussions with numerous tech CIOs confirmed CPQ as a pervasive and critical pain point, underscoring the need for a new solution.

"The reason is because um all of these tools were basically built in a pre llm era their data models are broken because they did not see consumption and a million skews and the sprawl that comes with that coming in order for them to basically build a product that handles all of the complexity and permutations they have to rebuild their entire data model and architecture from the ground up which is the same thing that basically most incumbents have to do today right which is why there's like so much frenzy around early stage startups in vc because in order for an incumbent to go do what a like a harvey is doing you have to literally rebuild that company from the ground up like you have to build the entire architecture differently"

Joubin Mirzadegan elaborates on why existing CPQ solutions are failing and why a complete rebuild is necessary. He states that these tools were designed before the advent of LLMs and modern pricing complexities, leading to fundamentally broken data models. Mirzadegan argues that incumbents cannot easily adapt because it would require rebuilding their entire architecture, creating an opportunity for new, AI-native startups to innovate from the ground up.

"The first is do not just go on their linkedin and look at all the fancy logos that they have gone and worked at and immediately assume that because they were at snowflake or because they were at databricks they must be good for your ai company it just doesn't work that way in fact in many cases it's the inverse is true where if you had to sell the number three product in a market and you had to fight tooth and nail and you were still successful there you're probably like if you go to a great company can i have a much higher proclivity to do well whereas if you were i don't know if you joined snowflake at 100 million of arr and you joined like their enterprise team in the bay area it's like yeah i get it but like that's not that impressive no offense to anybody that joined snowflake at that time there were some diamonds in the rough so i think that's that's one"

Joubin Mirzadegan advises against hiring sales leaders based solely on impressive past employers like Snowflake or Databricks. He contends that success in a mature, well-established company does not automatically translate to effectiveness in a startup, especially in the AI space. Mirzadegan suggests that individuals who have succeeded by selling less established products or in more challenging market positions may be better suited for early-stage companies.