The Ledger, every show

“If your PLG motion is figured out, but the PLG, if you miss it, and if you build the sales teams too early, it's very hard to build later.”

“If you know that you're gonna need to build a lot for this particular customer that is outside of your normal product roadmap, and that would detract your engineering product resources from building the core product, I wouldn't do it. It's very hard to say no …”

“And I think this lack of that level of commitment early on, I think at Dropbox was what plagued us. You know, we had wonderful, fantastic go-to-market leaders at the company, but we just had them, like each one came for, you know, a couple of years and then le…”

“I would argue actually that companies like Asana or Dropbox were a little too late into enabling the enterprise motion on top of PLG.”

“I think that the self-serve team is fundamentally a product team first and foremost, and it needs to be a product engineering team and sit within the product organization to be actually able to build the experiences for the customers on that enable PLG.”

“I think at Dropbox we launched the first region outside of the US when we were over a hundred million in ERR, and I think that frankly was too late. I think you can start doing this when you are at about 20, thirty million because it just takes a very long tim…”

“So if you're a head of sales, You don't go and talk to your salespeople first. You go and talk to your head of engineering or key engineering product leaders, because if you truly as a head of sales, you are going to need to work with them for the company to b…”

“I think if the founder sort of hires salespeople who he gives the playbook to that the founder developed, it's going to be less effective and less efficient than if Founder brings in the person and lets them create something that they would feel ownership over…”

“After you close to either several deals, or maybe you are up to maybe one million in revenue, it is time to hire your first head of sales.”

“No, the founder shouldn't and it's better that, that they're not. So of course the founder is the most, most often the first seller and most often you know, and they need to link the sales playbook to the vision of the product and the company they want to buil…”

“I think first and foremost, I'm looking for people who have not done the job before. So I usually, instead of sort of hiring people who have the experience, who have done exactly the same role before, which sometimes is appropriate, but for most roles, especia…”

“The second step is as a hiring manager, I try to have very clear must have criterias. Three to five must have criterias for the role. And I ruthlessly decline candidates who don't meet at least one of those criterias on the resume stage.”

“It's only the hiring manager who really, really sets the hiring bar and your panel will not be able, your panel doesn't exactly know what you're hiring for.”

“I don't think that there is a special breed of, you know, PLG salespeople. I think that, you know, say a great salesperson is a great salesperson.”

“Nearly everybody who has like, good experience have about 40 minutes to an hour talk track that they can give you that looks impressive, right?”

“So what I try to do for every leadership hire that I make I try to free up their first months as much as possible. Like, I try to create a situation where they don't need to deliver anything in the first one months.”

“So if you're a head of sales, you don't go and talk to your sales people first. You go and talk to your head of engineering or key engineering and product leaders, because eventually as a head of sales, you are going to need to work with them for the company t…”

“Anybody in the leadership role, their role is just too important, a lot more important than, you know, person's feelings or the process that you need to follow. And I try to lean as direct as possible. So like radical candor to the extreme, right? So you care …”

“And your job as the CEO is actually to make sure that you go and practically ask them, ask all of your team members, how do they feel about the new hire? What is the value that the new hire is delivering already? How is the new hire helping them up level and d…”

“The junior rep will consume bandwidth from the founder, and the founder will need to spend time on those first few reps to enable them, to support them, to show them what to do. And the head of sales will instead create bandwidth that the founder can use to go…”

“Enterprise takes multiple years to build. So even if you start today, it's not going to be until, you know, maybe three years, four years from now that you really figured out how to be a PLG plus enterprise company.”

“In the long run, I think the best business model that you can have is PLG plus enterprise.”

“Going into the enterprise is a commitment for the entire company that starts with the CEO and that needs to take the entire, not just the go-to-market teams and sales teams, but the entire like marketing and engineering and product and the entire culture of th…”

“I feel like I think about sales playbook on three different levels. The customer level, team level, and market level. So customer level for me is all about the problem and the solution. So the question is like, what problem are you solving? Who are you solving…”

“After, you know, you closed either several deals or maybe you are up to maybe one million in revenue it is time to hire your first head of sales.”

“If you are hiring your first head of sales, and if you know, have no idea how to hire head of sales, like, and what they should be doing, go and talk to Tan heads of sales who you may possibly maybe not be able to hire much larger companies, right, for not loo…”

“At Dropbox, we had this initiative to try to replace our final interviewer for a very long time has been the co-founder. Arash has been the co-founder. He interviewed every single person of the company until we were like 500 plus people.”

“If you don't see any results delivered in the first three months, if you see the person sitting and figuring out quote unquote strategy and drawing charts and not meeting customers and you know, not delivering anybody for the early sales team in the first thre…”

“I think the purpose of the deal reviews is primarily for your sales team to learn what to do well and what not to do well. I think your audience for the deal review is not the person who did the deal, but all the people around.”

“I think the biggest one is when salespeople feel that it's like any adversity in the deal review. When the deal review for the salesperson is like a review of their personal success, then it becomes a show. They become defensive. They show you only the things …”

“The biggest one actually is about 150, the Dunbar number when you as a person, as a founder, as a leader start to not know every single person in your team and start to lose the ability to control every single thing that happens at about 150 people. That actua…”

“Yeah, I think also the biggest learning for me is that is actually in hiding is, you know, hiding a person who sits across the ocean from you is kind of five times as important as the person who sits in the same office. It's just because it's hard to notice wh…”

“The way that we wanted to find people who could potentially replace Arash, we analyzed who said no more often and who was right in the hiring decisions more often. Like we took the entire database of our interviews for the company, and then we found those two …”