Insight
Marketing Sales Rely on Storytelling While IT Sales Demand Product Quality
“On the marketing side, A lot more rests on the go-to-market and having a good go-to-market story to tell and is less, a little less about the quality of the product. The quality of product obviously always matters, especially in retention and other things like…”
Insight
Gupta: Scaling sales to IT and security is easier than marketing
“I think it's easier to scale out selling to IT and security because there is a process that they're going to go through that's well understood. They are going to be very rigorous in testing out the capabilities and making their decision. And I think on the mar…”
Insight
Executive Candidates Who Have Never Fired Someone Are a Red Flag
“Shocked how many people I interviewed that were senior directors, VPs, never fired someone before. I was like, okay, this is a pretty big red flag to me.”
Insight
Gupta: New enterprise products only need one killer differentiating feature to sell
“One thing that I've learned and I've learned this from our CEO rubric and I, it's, Just really gotten embedded into the way that I operate is that you need to just have one killer differentiating feature that you can sell on to begin with. So whatever that is,…”
Assertion Supported
A Negative WSJ Article Forced LiveRamp's Pivot to Product-Market Fit
“We ended up having this Wall Street Journal article come out about the company that was really negative about the practices that we were using around data collection on the internet. So we ended up having to really shut that down and pivot to a totally differe…”
Assertion Not checkable as stated
LiveRamp churned zero enterprise customers while stripping 90% of legacy features
“We didn't end up turning any of the customers, even in this move, because what they actually cared about was this piece of the technology really working and We did that within nine months”
Opinion
Gupta: Most Product Leaders Lack Good Commercial Sensibility
“I think about this a lot because I think it's one of the big areas that most product leaders do not have good commercial sensibility.”
Disclosure
Rubrik Mandates Sales Certification and Pitch Training for Product Managers
“We've started having new product managers go through the sales engineering training. We just launched a new first meeting deck at the company and did a big training with our sellers. All the sellers have to certify, get certified on the first meeting deck. And…”
Insight
Gupta: Emotional detachment from discarded work is essential for pivoting
“Is figuring out how do you detach yourself from the work that you've done and from what has already happened and say, well, we're learning something new. We're going to pivot our focus to this totally new thing and do that over and over and over again. You had…”
Insight
Gupta: Startup founders should shield junior employees from executive stress
“I think actually something that the founders did really, really well is keep the sense of fun and not make the work itself become super stressful. So don't like, not transferring probably the stress that they were feeling. I have to imagine they were feeling s…”
Assertion Not checkable as stated
LiveRamp Suffered Attrition Finding Product-Market Fit Because Experimentation Ended
“There was actually like a big morale hit then, even though we were so clearly finding success. We lost a lot of people because they were like, well, I want to go build. Cause I said, we selected for the people that love just experimenting and building. And now…”
Insight
Gupta: Enterprise buyers prioritize one or two flawless features over broad toolsets
“Buyers don't necessarily need all the hundred features that are particularly going to make that outcome successful, they need the top one or two, and they need a roadmap for the future. There's a lot of times also where, like, if you have a hundred features, e…”
Assertion Supported
LiveRamp scaled from $30M to over $200M ARR between 2014 and 2017
“When we were acquired, we were thirty million ARR. In 2017, we crossed two hundred million ARR on the backs of getting these Fortune 500 customers from Axiom, and then being able to use those success stories to sell to other large brands.”
Insight
Gupta: Horizontal moves accelerate upward career trajectory faster than vertical climbing
“I have told people many times, giving them career advice, that moving horizontally within the company is incredibly valuable, and a lot of people think about their career and career growth as like, I have to just keep moving up and up and up, instead of thinki…”
Insight
Gupta: Sales engineering is an ideal background for product managers
“I have a few people on my team that before they did product did sales roles, SE type role, like sales engineers. I think that's an amazing background to have because then you have an understanding of what does it really take to sell a product before you have, …”
Insight
Gupta: Execs should do tactical product work before hiring leaders
“So I actually did that work myself until I brought someone on, and that actually gave me the context to then be able to help that person on board, understand the nuances of that business so I could make sure that I could shepherd that and hand that off success…”
Insight
Gupta: Companies building a second product should dedicate 100% GTM resources early
“I think when you think about building your second big product as early as possible, identify sales, S E marketing resources that are going to be dedicated to figuring out how to get traction with this new product together. And don't make it 20% of their job, m…”
Insight
Gupta: Poor execution stems from solving problems ten steps ahead
“Some people have a really hard time with systems thinking and breaking down a problem into a set of steps that you have to go through. So they get wrapped around the axle, mudging all of the problems together and trying to solve a problem that's actually 10 st…”
Disclosure
Gupta: Approached LiveRamp CEO whenever rate of learning stagnated
“When I ever felt like in my 11 years at LiveRamp, there were stages in time at the company and with my role where I didn't feel like I was learning, I would actually just go talk to the CEO about that and be like, hey, I don't feel like I'm learning as much an…”
Assertion Contradicted
Acxiom Paid One-Third of Its Market Cap for Unprofitable Startup LiveRamp
“Axiom paid a third of its market cap for a live ramp, a thirty million ARR company when Axiom probably had like, I don't remember, like probably eight hundred million in revenue at the time and high cash flow for this company that was like not profitable and h…”
Assertion Not checkable as stated
Gupta: Rubrik Product Team Initially Had Zero Cybersecurity Domain Experience
“We had no one on my team who had ever built or sold a security product before. I was like, this is including me. So I was like, this is pretty bad. If we want to be a security company and we sell a lot to IT, but we wanted to do more in security. It was like, …”
Disclosure
Gupta: Failing to plan second acts before core growth slowed was a LiveRamp mistake
“I think one mistake I feel like I made at LiveRamp is I didn't think about where was the new growth going to come from and when is the sellable addressable market really going to tap out or slow down and the speed at which we're going to be able to acquire new…”