Ep. 313: Today we deep dive into what startups can learn from the large SaaS incumbents of today.

Sarah Varni: CMO @ Twilio on her biggest takeaways from her time at Salesforce.

Erica Schultz: President of Field Operations @ Confluent on her biggest takeaways from her time at Oracle.

Whitney Bouck: COO @ Hellosign on her biggest takeaways from her time at Box.

Leyla Seka: Partner @ Operator Collective on her biggest takeaways from her time at Salesforce.

Ryan Bonnici: CMO @ G2 on his biggest takeaways from his time at Salesforce.

Ryan Barretto: SVP @ Sprout Social on his biggest takeaways from his time at Salesforce

Tien Tzuo: Founder & CEO @ Zuora on his biggest takeaways from his time at Salesforce.

Paul Albright: Board member @ Clarizen on his biggest takeaways from his time at SuccessFactors.

Jaleh Rezaei: Founder & CEO @ Mutiny on her biggest takeaways from her time at Gusto.

Eugenio Pace: Founder & CEO @ Auth0 on his biggest takeaways from his time at Microsoft.

Liat Bycel: VP @ Airtable on her biggest takeaways from her time at Twitter.

Mark Goldberg: Partner @ Index on his biggest takeaways from his time at Dropbox.

Pssst 🗣 Loving our podcast content? Listen to the start of the episode for a promo code to our upcoming events!


Ep. 314: According to a study from SiriusDecisions, the majority of buyers (81%) today make purchase decisions based on buying experience, over product or price. To meet buyers’ high expectations and manage the challenging sales landscape, companies must involve their entire organization in maturing the sales process- including after prospects sign on the dotted line. This session from Showpad CMO Theresa O’Neil will outline a practical approach to growing revenue and retention by aligning sales, marketing, and customer success.


This episode is sponsored by TaxJar.

SaaStr’s Founder’s Favorites Series features one of SaaStr’s best of the best sessions that you might have missed.

This podcast is an excerpt from Theresa’s session at SaaStr Europa 2019.


If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin
Harry Stebbings
Sara Varni
Whitney Bouck
Leyla Seka
Ryan Bonnici
Ryan Barretto
Tien Tzuo
Paul Albright
Jaleh Rezaei
Eugenio Pace
Liat Bycel
Mark Goldberg
Theresa O’Neil

Below, we’ve shared the transcript of episode 313.

Harry Stebbings: This is the official SaaStr podcast with me, Harry Stebbings, and we are just one week away from SaaStr Annual. So if you’d like to see all things behind the scenes from the event, simply head over to Instagram and follow @hstebbings1996 with two Bs. It’ll be awesome to see you there. But to the show today and I wanted to mix it up a little bit. So we’ve had so many guests who’ve learned their craft from some of the world’s leading institutions, including Salesforce, Dropbox, Box, you name it. And so I thought it’d be awesome to do an episode on what being at an incumbent fundamentally teaches you, and how it shapes your thinking when founding or joining start-ups. So we’ve brought together a collection of our favorite answers into a mashup almost, and I’d love to hear your thoughts on this style of episode, really. And you can let me know again on Instagram @stebbings1996 with two Bs.

Harry Stebbings: But that’s enough from me. So now I’m really excited to head into this mash up on the biggest learnings and experiences from working at some of the world’s leading incumbents.

Harry Stebbings: So we’re going to kick off today with Sara Varni, CMO at Twilio talking about her biggest takeaways from her incredible time at Salesforce.

Sara Varni: Yeah, I mean it was an incredible ride and honestly, I joined Twilio very similar time that I joined Salesforce. It was about 1100 employees [inaudible 00:02:03] million in revenue. And I just had the opportunity to pick up so many different skills, to build new programs. And I think it was just a great place to learn. You know, if I think about some of the things that really made Salesforce special, there’s just a huge diversity of talents. You had people from all different walks of life, from all different types of backgrounds. You know, I think there’s a common denominator of being hungry and really excited about the space, but I think it just made for a really interesting and unique culture.

Sara Varni: And then I think, also, it was pretty incredible to watch how Salesforce could move and pivot towards what was happening in the industry while still maintaining a foundation around CRM and the core business. And I think that all really came down to the way that Marc Benioff instituted planning process called the V2MOM process, which was about setting a big picture vision, setting values for your organization, and then the methods and the obstacles and the metrics that you need to lay out to achieve that. And that happened all the way from the top at his level to everyone throughout the organization. And it was really critical for us moving as fast as we were going, as fast as we were, to have that alignment to really do big things.

Harry Stebbings: So if we stay on Salesforce now, we’re going to hear from Leyla Seka and she’s talking about really her biggest learnings from seeing the hyper-growth of Salesforce also.

Leyla Seka: I mean I think this is where Salesforce got it right. And in many ways, because the reality is, when you’re running through scale like that, things are moving at a breakneck pace. I mean, I remember we’ve always done employee surveys at Salesforce, we’re always really trying to understand what’s going on with people. And through years we did the employee survey and I would get the results back. And the thing that everyone likes the most about Salesforce was how innovative we were, how we changed on a dime and how we made all these great things happen. And then the thing that everyone was most upset about was how everything changed all the time. And I was like, they’re the same thing.

Leyla Seka: I mean I think it, what we did a good job of early was paying attention to the human condition on scale like that is going on, when your job is changing, when new people get brought in, when the culture of the company shifts, when things start changing at–being a steward of that culture and really listening to the employees, the new ones, the old ones, that ones that live in other places, the remote ones, and trying to understand how to make each employee experience as rich and validating as possible during that scale. And that’s really the magic that Salesforce got right really well.

Harry Stebbings: And now we’re going to hear from Erica Schultz on her 16 year journey at Oracle and the biggest takeaways from her time there.

Erica Schultz: I did, I spent more than 16 years at Oracle and I learned so much throughout my tenure there. It was really an incredible experience. The experience I had was I was afforded so many different opportunities along the way and opportunities to build new routes to market, new methods of selling, taking new products to market like this offers a service offering. So I really got experienced as a builder, which sometimes people find surprising because it’s easy to paint people who come from big tech companies with one broad brush and assume that you’re always part of a mature business. But that was not my experience. Just a couple of examples, when I was a couple of years into my tenure at Oracle, I moved down to Latin America to Argentina, sight unseen, actually and built out a telesales group in Argentina. And then later in Miami,, hiring about a hundred people from 11 different countries.

Erica Schultz: And that early building experience really wet my appetite. I came back to North America, we built out the inside sales team in North America over the next five years, building hubs in multiple countries, including in Bangalore, India, and assembling a global community of practice. And then as I mentioned, in 2005 I took on the software as a service opportunity, which was a very nascent sales team and business for Oracle at the time. But I really found throughout my Oracle experience, this love for building. And of course I had the opportunity to work with really experienced operating execs who’ve taught me a lot about operating rigor, execution and working as a team. So it was a fabulous experience.

Harry Stebbings: Now we’re joined by one of my favorites, Whitney Bouck at Hellosign on her biggest learnings from her time at Box.

Whitney Bouck: Oh, a lot of big takeaways. I think the scale and rapid growth is first of all, one of the most exciting things to experience, at least for me, I love fast paced, I love high energy, I love change.

Whitney Bouck: So for me, that’s the perfect environment for me to be in. But I think the takeaways for me are that you also have to watch for burnout. You can sustain that pace for a long time, at least for me, I can do it for several years, but at some point, hey, you do need to take a break and realize that it’s not normal to run a million miles an hour, 24/7 weeks and weeks and months and months on end. So that was one of the takeaways. I think it does–It’s good for the body, it’s good for the mind to every once in a while kind of take a small break even if it’s a day to just recoup and refresh, if you will. And then I think another key takeaway was that those kinds of periods of fast growth and scale are the way to potentially earn your unfair share of a developing market. And so there’re windows of opportunity to be taken advantage of and not to be overlooked. So I think there’s kind of a combination of run fast and rest once in a while that I think is really a great learning for me out of that period.

Harry Stebbings: And now we’re going to be joined by Ryan Bonicci at G2 who talks about his learnings from HubSpot and Salesforce and really how marketing changes when you move to a startup.

Ryan Bonicci: I’ve kind of always viewed my career area, I guess is like I always want to go to a company whereby I don’t know that much about what I’m going to be doing, which is kind of sounds really counterintuitive. So when I was at Microsoft, I was doing consumer marketing and then when I moved to ExactTarget I was doing B2B. And so when I then joined Salesforce, Salesforce is very much like enterprise B2B marketing, right? So we were doing super high touch marketing activities in the sense of CMO events where we would rent a private jet and take 25 CMOs on a day trip somewhere. And it was all about relationship building with our sales reps, which is a super useful tactic. It works really well. We would generate 10 X like what we invested into that based on those people.

Ryan Bonicci: But it doesn’t really scale when you’re selling to the masses. And so to me, right, I want to run my own business in the not so distant future. And so I knew that I wouldn’t, when starting my own company, have a $10 million marketing budget to just go and stop organizing private jets through CMO events. And so I kind of realized that hey, I needed to build those skills around in that marketing really ROI focused marketing that compounds, that’s cost effective and that really works. And so that was where I was like, hey, I love HubSpot’s product and I fucking love the way they market. And so I wanted to become an expert in that. And you know, for the first six to 12 months, I was just in learning mode and I think it was from like month 12 to 24 that was really where I then felt like I started to push the needle forward for HubSpot in terms of what inbound marketing was. Cause I had learned as much as I needed to and I kind of do that with all of the companies that I move to.

Ryan Bonicci: It’s like the first six to 12 months, I am getting up to speed in what I didn’t know, then when I can kind of connect what I didn’t know in this new role with all of this stuff that I do know from my previous roles, I think that makes me then better than other folks that are coming in with just one skill set in that one space because they’ve always done the same type of marketing.

Harry Stebbings: I love that. In terms of the accumulation of knowledge, I do want to pick up, you said that about kind of your admiration for HubSpot in terms of their marketing going into the role. What did you love so much about their marketing that kind of inspired you to take the position and also be so excited to move forward with them.

Ryan Bonicci: You know, it’s a bit meta, but you know, as a, as a marketer, HubSpot marketed to marketers and you know, most of the companies that I’ve worked for, marketers have been my target audience. And so I think it just naturally felt right to me because I had already been consuming a lot of their content organically because I was a marketer and I was going to Google and I was searching for things that I was doing within my job, whether it was writing a press release, or organizing an event, or testing subject lines and HubSpot was always there to help me up level. And so I think that’s just naturally why I’ve made sense to me of this is a cool company, not only in product but also just from a philosophical point of view.

Harry Stebbings: Stay on Salesforce learnings. Now we’re talking to Ryan Barretto, Sprout Social on his biggest takeaways from his near decade at Salesforce.

Ryan Barretto: The first takeaway would be, be deliberate and explicit about your business plan. Write it down, share the rough draft with your team, debate it, prioritize it. Salesforce called it their V2MOM process and it stood for vision, values, methods, obstacles, and metrics and getting a chance to see Marc Benioff workshop that annual V2MOM with the management team was amazing. I remember a meeting when Keith Block, who’s now co-CEO, had just started. Marc actually made him go through his V2MOM in front of hundreds of people across our leadership team and Marc would be jumping in and challenging Keith on the priorities. Keith, what’s more important, method two, method three, method three or method four? Keith, why is three more important than four? It was actually a little uncomfortable to watch, but it really hammered home that if everything was important, nothing was, and that every single leader in the company needed to invest the same amount of time and energy in their own plans.

Ryan Barretto: The second takeaway I’d say, is just be maniacally focused on your customer. And I really believe that Salesforce pioneered the department we now know as customer success. Customers were at the heart of everything that we did and if you went to Dreamforce you’d see these massive posters of our customer’s faces on the side of the Moscone conference center, with the heading “Customer heroes” because they truly were the star of the show. And because the company was so dialed into what customers wanted, they’re able to disrupt the industry. All of a sudden they set this expectation that implementation should be fast and painless. A business user should be empowered to configure CRM without IT help, and you should expect free upgrades multiple times a year, and that you shouldn’t have to pay for all that upfront. And it was just a great reminder that your customers have a lot of the answers you’re looking for.

Harry Stebbings: I mean a lot of learnings and takeaways from Salesforce in this episode and we’ve got another one now with Tien from Zuora on his biggest takeaways from working closely with Marc Benioff.

Tien Tzuo: [inaudible 00:11:42] What if you look at a Salesforce trajectory, I mean from the outside it looks really smooth. I’d say there’s two big takeaways. One is for them to have been able to maintain their growth rate to where they are today. You know, $6 billion. That is a pretty significant accomplishment. And it’s not until you actually try to do one of these things, you’re on your own that you realize, to be able to deliver that consistent growth year in, year out over a five, 10, 15 year period–I think they’re 17 years old–is not easy. And so, hats off to Marc to be able to do that. The second thing is it looks all smooth from the outside, but when you’re on the inside it’s certainly crisis after crisis after crisis and that’s part of the fun. That’s part of the development. And you know, we could probably sell multiple books with stories from what we had to do to build Salesforce into what it is today.

Harry Stebbings: And now thrilled to welcome Paul Albright, who’s going to be discussing his biggest takeaways from his time with SuccessFactors.

Paul Albright: Yeah, very many. So one was to keep the perspective of the tenuous beginnings of SaaS because the model was not yet optimized. And that was clear. So for example, to get specific with it, if we looked at that vintage of company, whether it’s SuccessFactors or Salesforce, what I think of as SaaS 1.0, the sales rep, a blended sales rep across enterprise, mid market, inside sales for us was carrying a blended quota of somewhere around 780K per rep, and the attainment rate that that rep had was around 35%, so not a terribly efficient model, but good enough that you could create growth. The other interesting, interesting dimension to it was that ourselves at SuccessFactors as well as other companies were spending far less on marketing than sales. So we were spending about 30 cents on a sales dollar in marketing because marketing was more focused on product launches, brand, and events than it was efficient online marketing.

Paul Albright: And I think that was one of the big learnings was to–at that time, number one was, let’s make sure we have a value based selling model because we’re disrupting existing behaviors for how people buy and use SaaS products versus perpetual licensed products. And the second big thing was to make sure that we were efficient on onboarding reps as much as we could because that was going to move the needle in the numerator. The denominator focus was let’s make sure we’ve got customer renewals above 90% by logo and over a hundred percent dollar renewals. So there was a few key metrics and learnings from 1.0 that we could look at the next generation of SaaS companies when I was over at Marketo, which took those metrics and added some new ones to a new level because I think the technology had matured quite a bit, as well as the overall market.

Harry Stebbings: But now time for Eugenio from Auth0 to discuss his biggest takeaways from his time with Microsoft.

Eugenio Pace: Well, so many things about Microsoft. Microsoft is such a great company, really, and I feel so fortunate to be there. So the first takeaway is the platform mentality and it’s building stuff that not only does something for you but also allows others to build on top of it. And so that was one. The second one was the developer mindset, which obviously is one of multiple facets inside the Microsoft. But I took that away with us and we built our Auth0 around the developer persona and then the scale just doing things not for a handful of customers, maybe hundreds of customers, but doing something that will impact the lives of thousands or hundreds of thousands of millions in their case. You know, thinking globally, thinking about a presence around the globe, really. So those are kind of the three main things that I took away from them.

Harry Stebbings: And now we’re going to hear from Liat Bycel at Airtable and her biggest takeaways from her time with Twitter.

Liat Bycel: Yeah, I would say the biggest lesson that I took from my time at Twitter, especially in the early days, was never to shortcut on hiring. It’s so important to have a rigorous recruiting process, including checking references and back channels. You know, this was definitely a challenge for us at Twitter when we were hiring 10, 15, sometimes 20 people at a time. I mean it was so important for us to stick to the process. It was also really interesting to realize that it was really about hiring people that are flexible, resilient, and folks that really embrace change. When joining any high growth company, you need people who are amazing problem solvers, who are smart, scrappy, and can really thrive in a fast changing environment. I think you can coach business acumen and how to sell unique elements of your product and it is so much harder to coach or change attitude more in flexibility.

Harry Stebbings: But it’s now time for Jaleh Rezai at Mutiny to tell us about her biggest learnings from her time at Gusto.

Jaleh Rezai: I think the biggest takeaways for me were around culture and how do you specifically build a culture where you attract the most amazing talent and create an environment where they love coming to work every day. And for me, there’s probably three things in particular around that, that I very much adopted at Mutiny. The first one was because I was there from the early days when we were in this loft in Soma that would always get overheated right around 3:00 PM, from those days when there was just very few of us, all the way to when it was a very large company, I got to really internalize the impact of early decisions on the company’s DNA. So I could look back at 400, 500 employees and say we have a particularly analytical approach when it comes to problem solving because of X, Y, Z hire. Or because of these things that we implemented when we were very early and there’s good and bad that comes with that.

Jaleh Rezai: And so when I started Mutiny, I was very thoughtful about what type of company did I want to create? The first thing that I read was this Medium post on the values for the company. And at the time, my Co-founder and I hadn’t even finalized the plans to work together. And I really thought about what that means for me. What were the values that I wanted to be similar to Gusto? What were the values that were going to be different and more unique to me and I’ve kind of made every decision with those things in mind. The second thing that I learned there about the culture was just how to help people scale. I think watching what hyper-growth does and how people evolve in that environment was a once in a lifetime experience and I learned a lot about how to scale and nurture talent, including myself. And so leveraging external mentors, bringing in executive coaches very early on, doing monthly reflections to make sure that we’re constantly looking back at what happened the month before and what’s coming ahead and how do we want to adapt and adjust and setting expectations well with people and kind of investing in that growth was probably the second biggest takeaway.

Jaleh Rezai: And then finally this last one, you know I learned from Josh, which is all of the small tweaks and care that you need in order to build a great culture. It just takes so much commitment. Early on, I remember I joined ZenPayroll. This was like my second week or something, and I was just sitting in the kitchen doing some work and Josh walked by and there was some water on the ground and he was like in the middle of something. But he just stop, grabbed a paper towel, cleaned it, threw it away, and then left. And it’s such a small example, but it gives you the sense of, if you have this culture of, we want to take care of our office as like our home and there isn’t someone cleaning up after us and we have this humble existence as a team, small moments like that, that you watch and absorb that really kind of make the culture come alive.

Jaleh Rezai: And you know, I think as we grew, we had to scale a lot of our processes and things to maintain that culture. And you know, today at Mutiny we have a value that’s work should feel like play. And so we cook dinner together every Wednesday, we have a chore bot on flag, so that everyone can chip in. We have these like counter corporate mugs. There’s a lot of stuff that we do that creates and builds the type of company that we want to create. And I think to kind of wrap it up, like a lot of seed stage companies view things as, I’m so busy, we’re trying to get to product market fit, we’re trying to build a company. So first I’m going to build a product and a company and then once we get big then I’ll build a culture. And I think that that’s just such a mistake, culture is very much filled at that seed stage. And I feel really grateful that I got to see that at Gusto and can now take those lessons to Mutiny.

Harry Stebbings: [inaudible 00:19:52] final one now, but delighted to welcome my friend Mark Goldberg at Index on his biggest learnings from his three years at Dropbox.

Mark Goldberg: I learned a huge amount from my time at Dropbox. As I said earlier, it was a period of extreme hyper-growth. So I have a lot of lessons and it’s informed how I think about investing now on this side of the world. But the number one thing I learned was the importance of hiring. And just to give you an anecdote, when I joined, I had had I think like an eight week interview process. I just finally started and my boss at the time, who’s now the CFO of Dropbox, Ajay Vashi, took me aside and said, you’re going to spend 80% of your time the next six months hiring. And I was furious. It sounded crazy to me. All I wanted to do, there was so much work was to put my head down and do the job I’d been hired for. And I was just totally wrong. The right decision when you’re in hyper-growth like that is to make the investment in people. And it’s so funny looking back, because we hired tens of people into the organization together, and those people all created wonderful talent pyramids beneath them. So it was one of those things where it was counterintuitive in the time, but absolutely the right thing to do for the company. And it’s something I think a lot about now as an investor.

Harry Stebbings: I have to say, I so enjoyed putting this episode together. And I’d love to hear your thoughts. What do you think of this type of show? Do you enjoy the mash up? Do you not? Any feedback’s hugely welcome. You can do that on Instagram @hstebbings1996 with two Bs. I’d love to see you there. As always, I so appreciate all your support and I can’t wait to bring you a phenomenal episode next week.


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