Welcome to Episode 208! Anne Raimondi has more than 20 years experience driving growth at startups and building them into nationally recognized brands. She has served as a leader and executive for technology innovators including Zendesk, Survey Monkey, Blue Nile, and eBay. Anne is also a Lecturer in Management at Stanford Graduate School of Business, teaching two popular courses, “Startup Garage” and “POWer: Building the Entrepreneurial Mindset.” She currently serves on the board of directors for SendGrid (NYSE: SEND) and MyHealthTeams. If that was not enough, Anne is also an active angel investor with an incredible portfolio including the likes of Canva, ipsy, and Minted just to name a few.

In Today’s Episode We Discuss:

* How Anne made her way into the world of startups with Zendesk? How did seeing the hyperscaling of Zendesk impact Anne’s operational approach and mindset?

* Does Anne agree that certain individuals are destined for certain stages of company development? What are the leading indicators that one can or cannot scale? What are the inflection points in company growth where process tend to break? What can managers do to provide security in these times of change?

* Why does Anne believe that everyone should be a product person in SaaS? What are the inherent benefits of this product-centricity? How does the element of product-centricity change when catering to 2 customers, CIO and consumer? How does Anne advise on this issue of agency?

* How does Anne approach optimizing internal decision-making processes? Where do many leadership teams make mistakes here? What is the right way for leadership teams to communicate their decisions to the wider team? How does Anne approach ensuring cross-functional communication at scale?

* How has Anne seen her style of board membership change over the last 8 years? What has been an inflection point that has changed the way she thinks about what it takes to be a great board member? Who has been the best board member Anne has worked with? What made them so special?

Anne’s 60 Second SaaStr:

* What does Anne know now that she wishes she had known at the beginning?

* The right way for founders to view competition?

* What would Anne most like to change in the world of SaaS today?

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Jason Lemkin
Harry Stebbings
Anne Raimondi


Harry S: We are back for another very special episode of the official SaaStr Podcast with me, Harry Stebbings. If you’ve ever thought, “Oh, I wonder who is coming on the show over the next few episodes?” Well, head over to hstebbings1996 with two b’s on Instagram, and there we will be posting the schedules for the upcoming episodes. It will be great to see you there.

Harry S: However, to our episode today, and I’m so thrilled to welcome Anne Raimondi to the hot seat today. Now, Anne has more than 20 years experience driving growth at startups and building them into nationally recognized brands. She’s served as a leader and exec for technology innovators including Zendesk, Survey Monkey, Blue Nile, and eBay. Anne is also a lecturer in management at Stanford Graduate School of Business teaching two really popular courses: Startup Garage and POWer: Building the Entrepreneurial Mindset and she currently serves on board of directors for SendGrid and MyHealthTeams.

Harry S: And if that wasn’t enough, Anne’s also an active angel investor with an incredible portfolio, including the likes of previous guests in Melanie at Canva, ipsy, and Minted, just to name a few. I do also want to say a huge thank you to Karen Peacock for the intro to Anne today. I really do so appreciate that, Karen.

Harry S: However, it’s now time for the show, and I’m so happy to welcome Anne Raimondi.

Harry S: Anne, it is absolutely fantastic to have you on the show. I’ve been looking forward to this one for a very long time, having heard so many great things both from Karen Peacock at Intercom.Thank you so much for joining me today, Anne.

Anne R: Thank you for having me. It was very kind.

Harry S: Not at all, but I would love to kick off today, Anne, with a little on you. Tell me, how did you make your way into what I always call the wonderful world of SaaS–I know I need to get out more–and come to be one of the leading execs and investors that you are today?

Anne R: Well, I didn’t start out in SaaS. My background had been in product management and product marketing, actually, in consumer companies. So Blue Nile, eBay during a growth period, Zazzle, but I came to SaaS really through products that I loved.

Anne R: First company that was B2B that I joined was Survey Monkey. I’d been a customer a number of times over the years, and I understood the approach. It was really focused on the end user, what are her needs, how do you make her life better, and building a product around that. It just happens that the people paying the bills are companies versus the end consumer. So that was my entry, really, into SaaS.

Harry S: I absolutely love it. I do have to ask though Anne,given that introduction and your early days spent at eBay and Zazzle, as you mentioned, two of the most prominent consumer companies of the day, we constantly hear about the consumerization of enterprise. I actually chatted with your fellow board member at SendGrid, Byron Deeter before the show, but he and I are super interested, how do you think that a start in consumer affected your enterprise mindset today?

Anne R: I think the way it affected my mindset going into enterprise was to always keep that end customer experience in mind. I really believe if you build a great product for that end customer and really focus on how we are making her life better, you’ll build a great business around that. And I’ve had the privilege of working with great founders with that mindset and I think what happens is when there are hard decisions to make–trade-offs on prioritization, where to invest resources–if you have that guiding principle of doing right by the end customer, it does help you make those tough trade-offs and really build enduring brands and companies.

Harry S: Yes for sure it does and that kind of customer-centricity often leads to growth and I want to discuss the growth element. I’m really aligned to the scaling of people starting today. You’ve seen many organizations where employees scale within a very high-growth environment, so starting on the macro, many on the show, have said to me before that certain people are destined for certain stages of a company life cycle. From your experience really at the forefront of many companies scaling, would you agree that’s there’s a lack of human plasticity to scale with the company?

Anne R: A great boss of mine once shared super helpful insight on this front and that it is nearly impossible for people to grow at over 100 percent year over year. You can be think about the only time in our lives where we experience that rate of change in our ability and our intelligence is when we’re babies in the first three years of life and change is just hard for people. No matter if we intellectually understand that growth and being in a growth company is good for us and good for our careers. The day to day of adapting and changing at that pace can be really exhausting and so I think that when I think about that as the context, it does help explain why not everybody is going to stay with the company through all the phases of growth.

Harry S: Can I ask you, you said that about why some and some maybe not. Are there any leading indicators that suggest some can move with the scaling of the company and some maybe can’t scale like others can?

Anne R: I do think that what I’ve seen with employees that really thrive in growth environments and stick with it through many phases is they’re able to adapt and change and they don’t mind the ambiguity. In fact, more than that, they thrive in environments that are uncertain because they find the ways and places to create solutions and they really enjoy that aspect of it so they’re really focused on what can I do to make something better versus wow, all the stuff around me is changing. I think those are the types of folks who can stay with it longer and actually really enjoy it and thrive.

Harry S: I love that kind of thriving on adaptation, but a lot of founders listen to the show, Anne. The kind of big question is when they’re scaling their organizations, what are the inflection points within company growth where maybe existing systems and processes break down? What have you seen those twinges of pain in company scaling?

Anne R: I definitely have seen sort of the first one being when the company gets past around 30 people and that original team that built everything together when titles didn’t matter and you all knew what the next milestone was or which customers you’re going after. I think that’s the first inflection point where change happens, so that’s one to think about as a founder.

Anne R: The next is what I would say is around doubling from like 100 people to 200. Often times that’s where experienced leaders are brought in, maybe to manage a function that before was shared across a couple people or didn’t … Wasn’t really official. Maybe you didn’t have a marketing team. There’s just a few people doing marketing and then all of a sudden, we’re going to hire a VP of marketing. I think those are inflection points where leaders often can tend to bring their own people and processes with them and that creates a lot of change. And then there’s definitely the point when you get past 500 employees and it’s really just hard to know everyone at that point.

Anne R: And there’re times where you don’t meet colleagues face to face and you only talk to them on Slack or email and some symptoms that are culturally hard is all of a sudden people talk about colleagues as, oh, the people in marketing, the people in finance versus oh, it’s Jim, my colleague who’s helping me with this. I would say those inflection points are ones for founders and leaders to watch and be really conscious of and help manage through.

Harry S: I love that element of kind of when you lose the naming and I’ve never quite heard it like that. Can I ask, Anne, have you seen any great cases, great examples, or what advice would you have to really encourage seamless communication, maybe across company, across function, across location. Are there any kind of secrets to really enjoying the benefits of good communication that have worked well?

Anne R: I wish I could tell you there is a secret or a silver bullet. I think it’s hard work, so perhaps the first is just acknowledging that it takes a lot of work to communicate well and something that we used to talk about a lot at Zendesk as a leadership team is we may have exhausted ourselves talking about and debating a certain strategy or decision. The number of hours spent on some of the toughest decisions were really high across the executive team. And then we’d make a decision and we go roll it out. And we can sometimes forget that everyone else in the company hadn’t gone along that journey of that debate.

Anne R: The discussions, the pros and cons, and we were just launching an answer to them and so even if we had exhausted ourselves talking about it, we had more talking to do. More bringing people along with us, sharing the context, sharing the why, answering questions, getting input… That those hours spent after a decision had been made are more critical to success often times, especially in a growing company. So I think the short answer is you just have to put the time in and you have to remember and empathize with the experience that everyone else is going through, not just your own as a leader.

Harry S: You mentioned that the communication from leadership teams down to the broader team itself. I do want to touch on kind of both sides of the table there. In those times of super high growth as often a Fabian element of the vulnerability or insecurity on behalf of the employees. Is there anything that managers can do to really provide context and security with all the rapid change that’s going on?

Anne R: I think one is just make it a priority, make time for it. Whether that’s just the continual check ins, whether that’s having open office hours where people can drop by and ask questions. I like asking open ended questions of people on the team too to make sure I’m listening well. Asking what have I shared that’s confusing or uncertain because I’m positive there’s something that I’m doing that doesn’t make sense. Taking that input of what’s confusing or challenging right now, what doesn’t seem to make sense, what could we all do better? If there’s one thing we could change as a company or I could change or do differently as a leader, what would that be? And just asking those questions and those open ended questions. It’s remarkable what you can learn. It’s remarkable what employees want to share because they want the company and they want the team to be better. I think making the time for that is really critical.

Harry S: I’m really pleased you said about employees wanting the company and the team to be better. Because on the flip side, what could maybe employees do, to really be empowered and thrive in these high growth times?

Anne R: I think there’s a few things I see people do to really thrive. The first is learning to be comfortable being uncomfortable, to be able to handle a certain level of constant ambiguity. And I don’t think that you’re born with it or not. I really think it’s something that people who do really well, they work on it and part of that is focusing on enjoying problem solving versus feeling like stuff’s happening to you. It’s changing–the moment you feel like this stuff is happening to me… I see people who practice being comfortable being uncomfortable, they pause and they think about, what’s my role in this and how do I make this situation better and how do I solve this problem and who do I involve? And who do I ask for help from? They pause instead of letting it run over them and feel overwhelmed.

Anne R: They know how to stop and actually change their mindset. The second that helps out a lot is I see people thrive who build strong relationships across the company, not just with the cohort of people they join with or if they were a veteran of the early days. It’s not just those friendships. It’s really people who build relationships with new employees who really care about new employee boarding and who build relationships across teams because they just genuinely like their colleague, but it also helps them stay much more informed and engaged. And then probably last is, people who really love what they do. They allow the customers they serve, they love the problem being followed, and that goes a long way to keeping you motivated and happy during all these periods of change.

Harry S: These very special people that you identified with those characteristics are available but they’re also rare. And I do have to ask, in terms of determining whether you have one in the interview process, my obsession is always with the interview process itself. I’m interested on do you have a favorite question to ask in an interview that you find maybe to be the most revealing of an individual’s character?

Anne R: One I really like asking is about someone’s values, what their core values are, and how they would describe them, why those are their core values, how they were formed, whether it’s influenced by their family or their education or number of things? I learn a lot about somebody by hearing how they describe their core values. And for me some of what comes out is, back to your question on people who are these special people who thrive in these growth environments. I find that they’re often people who are very intellectually curious. They just are. They’re really engaged. They ask questions. They are a wonderful balance of humility and confidence, knowing that they don’t know, and so being willing to ask questions and grow and develop and embrace feedback. As well as competent in their ability to work through a situation and to persevere. That blend often comes out when I listen to people talk about their core values.

Harry S: Staying on the theme of people. I do want to stay on this, but speaking about something that you said to me before which is kind of about the product-centricity of people and the requirement to be so. Can I ask what did you mean by this and why is it so important to have this product-centricity maybe throughout every function within the organization?

Anne R: Yes, and I definitely will put my bias out. Starting my career as a product manager and I’m definitely biased toward product people but what I mean–and not everybody has to have been a product manager to be a product person. What I mean by a product person is, really again focused on what do we provide for our customer? What is her life look like? What’s the complete solution she needs to reduce her pain point and make her life better? And part of why I think great organizations, everybody in across the company has a product mindset is because it’s increasingly easier and faster to build software and a truly standout product is what you need to win. And a good example of why I think having that product mindset and understanding what your product provides and who your customer is, is important regardless of function.

Anne R: Let’s take people ops. If you’re in people ops and you know who your end customer is and you know what the product is that you build today and also where it’s headed and how it’s used, that helps you find better people for the company. Recruiting is better and helps you coach employees so that they can thrive in their career. You can anticipate what departments are going to grow and how do you coach someone to be able to build the skills and experiences so they can take on the next role and the next role. And that same philosophy goes for every team, whether you sit in finance or IT or workplace. It’s not just salespeople, the support folks or the product folks who need to know the customer and the product. It also helps build a unifying organization around a central mission and purpose and if everybody is focused on the customer.

Harry S: And, Anne, I did love the customer focus there. The kind of element that always strikes me though, when there is such customer focus is how do you think about the balance maybe between being customer-informed versus customer-driven and taking the Henry Ford quote of building a faster horse and is that a thought for you?

Anne R: We do hear that a lot and I think people also mentioned they think about Apple. Would a customer have told you I want a mini computer in my hand that does all these things with these apps? To me, the customer driven means you are really paying attention and listening to an empathizing with customer pain points. You’re not asking your customer to design the end solution, but what you care about and you care deeply about is, what is causing friction in his or her life. What is a really hard problem that they’re facing that they would value you solving for them. And then you use all your creativity to brainstorm and test the possible solutions to meet that need, but it’s picturing and living their life. To me, customer informed feels like you’re picking and choosing what you listened to because you think you know better than your customer what their pain is versus customer driven is we’re going to truly empathize with what’s going on in their life. We’re going to listen to the not so great feedback and we’re also not going to settle for providing a mediocre experience.

Harry S: One thing that immediately strikes me with this is when you serve two masters, so to speak, when you have maybe lower-end devs in an organization, but you’re selling to the CIOs, how do you think about customer-centricity and customer love that when essentially you have to serve two masters and one’s the ultimate buyer and there’s that problem of agency, does that change the situation at all?

Anne R: I wouldn’t be honest if I didn’t say there is that tension as you move up-market and have enterprise customers where the ultimate decision maker and the budget owner is unlikely to be the person who’s using the product day to day. But I will say the good news is that, modern companies care deeply about employee experience with any software tool. Right? And the beauty of SaaS and self-serve, and the ability for employees to try a product, put a credit card down and start using it, is that the employee’s voice, the end user’s voice and decision making is louder and more powerful and more meaningful.

Anne R: We saw that time and time again at Zendesk. Maybe we had chosen to be an enterprise customer of one product, but a competing product could take over and we could wake one day and this happened to us a number of times where more than half the employees were using something else. And of course we were going to switch. Right? Because that made employees more productive and happier. I do think it’s probably more a matter of how do you build relationships across and throughout an organization as a company, knowing that you’ve got a decision maker and a budget owner, but also knowing that to stay competitive and stay relevant, those end users have to love what you’re doing.

Harry S: Can I ask, do you think when selling into company and gaining those customers within the company, do you think you’d have to have multiple champions within the organization in case, especially with West Coast churn on the employment side in case they leave and you lack that internal champion? Is it important to have multiple?

Anne R: I think it is important to have multiple people within an organization know why you and your product matters, what it’s providing for the company, what value it’s generating for employees. Another way to think about it is, let’s be realistic about who’s telling your story when you’re not there. And so having multiple champions across the organization can only help. So when these discussions come up around renewals or expansion or buying more products, perhaps you’ve put out a product that’s in beta still and it’s early. Who’s going to tell the story internally that says, no, this is the company we want to bet on because we believe they’re building something that will solve our problems and they’re the one we want to be with in the long term. Absolutely making sure that those relationships are as broad and deep as possible. But that goes back to understanding your customer deeply and what goes on when you’re not there.

Harry S: Absolutely. I love that element of who’s going to tell a story when you not there. But I do want to take the chance, I’m a geek when it comes to all things boards. And I have to take this opportunity with you today, but you’re on the board of multiple incredible companies, one of which SendGrid. And I do want to discuss your style of board membership, and I’d love to start with how have you seen your style of being a board member change over the last seven years?

Anne R: I think my style has evolved certainly based on my experience at Zendesk as we grew and I grew as an executive of the company and interacted with an incredible board. It definitely influenced my style in terms of what questions to ask, right? Ultimately, as a board member, you’re not an operator and what your role is in governance is ensuring that the company and the executive and the team are able to achieve their wildest biggest goals and build an enduring company. And it’s focusing on, what questions do I ask and when to ensure that we’re thinking about things strategically and comprehensively. And also how to make sure that I’m relevant in these conversations by having context. To me that’s also building relationships, not only with the CEO but also with the exec team, with employees and so I’ve got context.

Harry S: I think that’s an often left out element in terms of building those wider relationships. In terms of change, I always love inflection points. Is there a moment that resonates with you on a board where maybe if your style and approach changed because of that moment and that realization? Is there a moment like that for you?

Anne R: I don’t know if there was one moment, but I think the hard moments are probably the ones that I learned the most from when you see a company have to make a pretty strategic decision that is going to change the course of what they do and how they do it. On the Bloc board, Clint was awesome CEO and had to make a decision of merging the company with Thinkful and that comes with it all the ramifications of, is the team going to stay, is all of the team going to stay the same way and combining with another entity is no small matter. And I do think it’s these tough junctures when CEOs and exec teams have to make decisions that they know are going to change the trajectory of the company that where either the best comes out or the worst comes out. And I’ve been really lucky that all the organizations I’ve been with, the tough situations have brought out the best in people.

Harry S: Absolutely. I love that. The tough bringing out the best. But as I said, you’ve sat on many great boards and I have to ask the tough questions, but this one I’m super intrigued by. From all the board members you’ve worked with who sticks out in your mind, Anne, as maybe one of the truly special ones and what was it about them that made them so special?

Anne R: Is it okay if I have two, because one would be too hard, even two is hard given the incredible caliber of people I’ve been privileged to be … either work with them on our board as Zendesk or serve with them. I’ll start with the Zendesk board. Michelle Wilson, who joined right as we were becoming a public company, just had such a huge impact on me. She’s a long time exec from Amazon and just her perspective, her integrity, and her willingness to spend a lot of quality time with execs on the team to learn the business and our perspectives, build relationships with us and then just seeing how she conducted herself. Again, always great questions, always a great listener and then always willing to bring out tough issues in the right context and setting to help drive decision making, drive change when it needed. Just a great mentor for me and then-

Harry S: Love that. That’s one.

Anne R: I can’t believe you’re not letting me have time to go through everybody who’s awesome, but I realized that it would take up more than the 20 minutes for the entire podcast if I got to sing praises of everybody.

Anne R: And then the second for me is Fred Ball, on the SendGrid board, and part of that was my experience joining my first public board and Fred is a great–He chairs the audit committee, he is a longtime SaaS exec, but more than that, more than all his experience, he does such a great job including everyone. And what I mean by that is, he really pays attention to who’s talking in a certain situation, who’s brought different things up and he’ll always ask if you haven’t heard from someone, he will always say, let’s take a moment. There’s a few people who haven’t spoken up and I want to hear what they have to say. And it makes such a big difference as a new board member to be welcomed in such a way. He would take time outside of board meetings to jump on calls with me, to get me up to speed on certain things and it was just the most welcoming experience I can imagine. I have to sing his praises and give him a shout out for that.

Harry S: Now I have to say that really is a special quality of a board member, that’s awesome to hear. I love hearing that. The final one, and it’s moving to the flip side and the operational perspective, what do you think founders can do to really get the most out of their board?

Anne R: I’ll talk about the strategic thing that I think founders can do and then a tactical thing that I’ve seen really work. On the strategic side. I think it is really thinking about where your journey is going, what are your big bold ambitions and therefore who are the people you’re going to need around you for that journey and what are the different diverse views and experiences that are going help you get better and be better? And really thinking about that as you build out your board and again, back to comfort and discomfort. Of course we want people around us ideally who we’ve had a relationship with and that we trust, but I think challenging yourself to build new relationships with people who again are going to bring a perspective that you might not have today, that’s going to help you in the next two, four, 10 years can really change who you look at and who you reach out to.

Anne R: And then tactically, this is again just giving credit where credit is due. Both Mikkel at Zendesk and Sameer at SendGrid both wrote letters to the board before board meetings. Even though there were a great decks produced, all the content that you would expect across the business, each of them took the time to write letters, narratives to the board ahead of time, and what it did was really point out what was on their minds, the tough things that they were working through that they wanted the board’s help on and that perspective. I think that narrative perspective gave such depth to the conversations versus just slide decks. I was privileged to learn from two of the best and I think that goes such a long way. I would love to see more founders do that.

Harry S: My word. I’m so pleased we did this segment on boards. I’m loving this, but I do want to move into my favorite of any interview, being the quick firearm, the 60 second SaaStr, Anne, I say a short statement and you give me your immediate thoughts, are you ready to dive in?

Anne R: I am.

Harry S: The right way for founders to view competition-

Anne R: Look at it clinically. What is your competitors value prop and what would your customer value from what they’re providing? And then take that and figure out how you’re going to do better.

Harry S: When is the right time to pour fuel on the company fire?

Anne R: I think when you’ve got confidence that the fundamentals are working and that your customer truly loves what you’re providing and then you’ve got this belief that there’s so many more customers out there to get. That’s when you pour fuel on it. If you’re getting a meh reaction, it’s not time.

Harry S: We constantly hear about the playbook, so to speak. Is there one? What are the dangers, the copiability, how do you feel when you hear playbook?

Anne R: I feel like it’s overused. I think there’s fundamentals, whether it’s the funnel or building pipeline that are common across. The danger of believing there is a playbook is that you’re not focusing on the uniqueness of your customer and your business and you’re thinking that somebody else’s set of rules is going to apply.

Harry S: What would you most like to change in the world of SaaS today, Anne? I’m giving you a magic wand.

Anne R: I’m going to use my magic wand to change what I think is the regression to the mean on pricing. I feel like every pricing page and packaging is all starting to blur together and look the same. I would love to see some unique, out-there different takes on pricing.

Harry S: That is far too tempting for me not to just ask. Is it bad to copy pricing if it works already? And I often have first time SaaS founders be like, “I have no idea on pricing. It works for X. Can I just copy it?” How do you feel if someone asks you that?

Anne R: I think what that misses–pricing–don’t get me wrong…. Pricing is complex, but I think if you just take what someone else is doing, again, like you miss out on having some interesting conversations with your customers and prospects around real value creation that you are providing and what then opens up the doors to how you price and package. I just think there’s more to do there that could be really interesting and then partly that then you’ll have conviction around, right? If you’re going have a tough conversation with the customer about pricing, the last thing you want to do is say, well, we priced this way because everybody else prices this way. You have nothing to stand on. If you’ve done the hard work of figuring out why and value creation, you’re going to have a much better conversation around why you’ve priced the way you’ve priced.

Harry S: Listen, I love that design to change pricing and I just stayed with you there. But I want to finish on the final element and that probably the hardest question of all, so I’m sorry for that. But what you do know now that you wish you’d known at the beginning. I’ll let you choose the beginning. It could be the first board in 2011. It could be the entry into the consumer world or then the SaaS world with Zendesk. But what do you know now that you wish you’d known at the beginning of…

Anne R: I think, and this may be the beginning might apply to any of those junctures. I think my big lesson learned that I wish I’d known earlier and I wish for others that they know as early as possible is, make sure you fall in love with something enduring, whether that’s your customer, your team, the problem you’re solving, don’t fall in love with ideas, fall in love with things that are more enduring. Because the ideas should change and evolve, but your fundamental passion for your customer, the people around you and the problem should be where you spend that precious time.

Harry S: Anne, it’s interviews like this that made me fall in love with podcasting. That’s much soppier than I meant it to sound. I cannot thank you enough for coming on this show, seriously it has been so much fun, thank you so much for joining me.

Anne R: Thank you. I’ve had the best time. I really enjoy it.

Harry S: And I have to say I really did just love that conversation with Anne. And if you’d like to see more from Anne you can find her on twitter @anneraimondi. That really is a must. And It’d be great to welcome you behind the scenes here at SaaStr. You can do that on instagram @hstebbings1996 with two b’s. It’d be great to see there.

As always, I cannot thank you enough for your support and very excited to bring you a special episode next week.


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