From exec roles to board seats - Anne Raimondi's leadership lessons for the startup C-Suite

[00:00:00] I think that that differentiates the best executives, where they're truly a team player and they care about the whole business, even if they're just responsible for marketing or sales or product from a title or on paper standpoint, that they holistically look at the business and the company. And I think that is a differentiator for the most successful executives.

And it also allows them then not to just stay in that lane that they came in, but to take on whatever the next most important initiative is for the company

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for today's episode of in depth. I am thrilled to be joined by Anne Raimondi ANZ had a long and impressive career with pit stops at some of the most interesting companies around. She was part of the founding team@bluenileduringthe.com boom. She then worked on the product marketing side of things that E-bay during its rapid growth.

And then after leading product marketing at survey monkey, when it was just 30 employees, she started a company that was acquired by task rabbit, and later shifted to operations as an SVP at Zendesk, where she led all internal facing teams for five years, she's currently the chief customer officer at guru, which is a knowledge management platform.

She also sits on the boards for Gusto, Patriot, and a sauna, and is a lecturer at Stanford's graduate school of business. What stands out of course is the breadth of these roles. Anne's been a founder operator executive and a board member at both consumer and enterprise companies at all different scales.

She's headed up product marketing, revenue and operations at big names throughout tech, giving her a unique range of functional expertise and lots of insights into different leadership teams and executive roles. And that's the focus of our conversation today. We dive deep into what makes for a great exac in board member, the pattern she's seen across her career and how leaders can grow into their roles.

What I found particularly interesting is how clearly she's crystallized the lessons from each chapter of her career, from what enables the best executives to scale up to how she's approached her own 30, 60, and 90 day plans as a new exec and doles out spot on advice for getting this critical transition, right, and sidestepping common traps.

She also touches on her systems for executive recruiting and interviewing, and when she minds executive talent internally, rather than defaulting to external hires, Finally, we discuss her impressive board work and the essential ingredients for productive, impactful boards across every growth stage today's conversation is a must listen to for executives, founders, and board members looking to level up their leadership frameworks and for folks who someday hope to step into those shoes, I hope you enjoy today's episode.

And now my company. Awesome. Well, thrilled to have you on the podcast. 

[00:03:50] want to start, was talking broadly about executives. What makes an executive great. And I'm specifically excited to talk to you about it because you've seen it from so many different angles in so many different types of companies at different scales.

And so maybe a good place to start is when you think about common characteristics across the best executives you've worked with, or when you think your best as an executive, what are the characteristics or behaviors that you see in those folks? 

[00:04:19] I think of it really as great executives are great leaders, as well as great managers and the trades specifically, I think the most successful executives, meaning that they're successful in multiple places in multiple settings, not just in one company, that's a brand name, that's grown a lot, but that they're really adaptable.

They stay curious and they're just genuinely interested in learning deeply about the customers, the products, the team, the needs. They might have a ton of amazing applicable experience, but they don't come into a situation. Trying to apply a playbook. They might rely on that once they're really grounded in the particular situation and need.

But I think that curiosity is just one of the most important traits I've seen in really successful executives and leaders. 

[00:05:21] Are there other things that tend to tie all the best folks together? 

[00:05:25] Yeah, I think that they genuinely. Want to make the team around them successful. And that means both the executive team, as well as their own team and function that there are some, I would say, good functional executives who come in and they're great at their department or their lane.

Like they're exceptionally talented and they make an impact, but they just see their team as that team versus also seeing the executive team being one of the most critical teams. To keep healthy or make healthy and continue to improve. I think that that differentiates the best executives where they're truly a team player and they care about the whole business, even if they're just responsible for marketing or sales or product from a title or on paper standpoint, that they holistically look at the business and the company.

And I think that is a differentiator for the most successful executives. And it also allows them then not to just stay in that lane that they came in, but to take on whatever the next most important initiative is for the company. 

[00:06:39] So can you share the stories or some of the folks that come to mind when you think of just really exceptional executives, a moment that stands out or some of the things you took away from watching them operate.

[00:06:52] Sure. I've been really privileged to work with number of and continue to work with a number of reasons, talented executives. I'll start with, I spend a lot of time with Lexi reset Gusto. She's just a standout, I think, both in how she's grown her teams, the business, how she's a partner to the founders, how she really is able to do, especially in a growth setting, the combination of like a deep dive, she can roll her sleeves up and dive in.

Recently the customer operations group was going through some changes and she just dove in there. She does that with sales, but then she also knows when to kind of zoom back out. And that's also a unique trait. I think that's really important with executives knowing not to be a micromanager, but knowing when.

Diving deep and getting context can help you and help the team be more successful. So Lexi's absolutely a stand out when I was at Zandesk. It was really amazing to see Adrian McDermott and his journey with that company. Having started. He's one of those executives that started when the company was small and managing engineering, and then growing into being able to manage a globally distributed engineering and product team.

Be strategic on both what should be built internally and what should be built through acquisitions. And that ability to scale from a 30 person company to a thousands of people, a company is unique as an executive and part of, I think what makes him great is he continually look at like, well, what comes next?

And how do I grow into that? I think a lot of that also comes from the DNA of Zendesk and that's how McKell the CEO and founder operates too, in terms of like challenging themselves and not getting comfortable. 

[00:08:52] Is that the key thing that allowed that executive to scale, it was just a constant questioning of what's next?

What are the gaps? How do I get there? Or was there something unique that made that individual be able to do that, which is quite rare to your point in terms of going from. Tens of people to maybe almost 10,000 people or something like that. 

[00:09:12] Let's say it begins with like a humility. And I know we're talking kind of execs.

And I went over into founders a bit too, because I was thinking of like other exceptional people. And I have the privilege of working with founder CEOs who also are in the bucket of executives. So we can spend a little more time on that too. But I think that common trait is this humility that starts with like in many cases.

Okay. I am in the biggest job I've ever been in, or I'm leading the biggest team or I'm taking on something I've never done before. And to have the humility of saying, well, what's going to make me great at it. What's gonna make this team exceptional at it. And how do I. Fill the gaps that I have, how do I go seek outside help or help from my board and investors?

Or how do I reimagine how I'm running a certain team, everything from tactical, how do I reimagine how I'm doing my one-on-ones and leading my team meetings and what my team needs to. All right. I've never led this function before. I'm going to go meet a bunch of people who are known for being great at this function or having scaled this function to three X.

What mine is right now, and I'm going to learn from them, then I'm going to hear what they've done, but then I'm going to come back and I'm actually going to. Apply it. And I'm going to get feedback on how I'm doing. I think that's a critical part of the humility is like I'm figuring this out. And so I need people to really be critical of me and help me see the gaps so I can keep working on that.

And I think that's what I've seen the most successful execs who can truly scale and then the confidence again, to hire people around them that they would work for. I think that's another really key trait of great leaders is being really confident that I'm going to find people much better than me at not just the function, but I'm going to surround myself with people that are better at me at the things that I need to work on.

And I'm not going to only hire people who have less experience than me. And that's another, I think key attribute of leaders who've built just incredible teams. Who've been able to do things that no one imagined they could do on their own. And then they achieve that as a group. 

[00:11:25] On that point. When you think about building out your own team and through the course of your career, recruiting people better than yourself, is there a specific approach or way that you did that other than sort of the obvious thing, which is starting out with a desire to hire that level of talent?

[00:11:40] of what I enjoy about hiring and building teams is understanding people's motivations because the reality and you all see this all the time, right? Is that really talented people have so much choice. They can go anywhere and people who've. Worked with them before are trying to recruit them. They have opportunities to start their own thing.

And so I think with hiring, for me in the past, it's been understanding, okay, what's going to be interesting and exciting and a growth opportunity for somebody that then fits with what I am, the company that I'm at can provide. And so in concrete terms, that might be someone who's been really successful in later stage companies, but wants to be a part of growing an earlier stage company.

And they're excited about sort of the build stage. So looking for those people in companies that might be bigger, same flip side people who've just are functional experts and I've just demonstrated they can build from the ground up and now are really interested in, okay, where's an opportunity to scale.

And so understanding kind of career motivation, understanding personal motivation and values and culture. So often again, like the most talented people, because they have choice. I find that a lot of the really outstanding leaders at any level, they actually care the most about the people around them.

They care the most about the values and the purpose of a company. And so spending a lot of time talking about that and letting them see the inside of the company and team and not just doing the traditional. Interview recruiting process. My goal is that whoever joins the team is just super excited to be part of it.

And there are no surprises there because the inside of every company has its challenges and being really honest about what those challenges are and making sure those are the challenges that someone's excited about solving, I think creates the best opportunity for people to thrive. 

[00:13:50] What have you learned or have you updated your internal frameworks from the worst hires you've made or the worst senior hires you've made over your career?

[00:13:59] There's a higher failure rate in leadership roles, or often the term is organ rejection. And the 

[00:14:08] costs of those mistakes are very high as well, because a lot of them are building a team around them and all sorts of other stuff. So it obviously makes sense to try to 

[00:14:16] get it right. Yeah. It's really true.

It's worth spending a moment on that. Cause you mentioned something really important, which is like cost and it's not just like the cost of time of having brought that person on and onboarding them or the cost of replacing them. The worst ones are aware. There's scar tissue left on the team and there's cleanup after and there's trust damage done.

And that costs a lot to the team in terms of how to fix what became broken. And usually in the vast majority of cases, none of them, this is intentional. It's not like an exact came in intending for it, not to work. Almost everyone goes into these situations very much wanting it to work. But if that upfront relationship building, if the expectations aren't aligned, if a number of things have gone wrong, that the damage can be really expensive.

Just from a human standpoint. I've definitely lived through that. I think the mistakes go back to some of the things that we were talking about, like what makes a good leader. Some of the ones that I've seen high failure around is that the exac has been exceptionally successful at their last place. They built something that worked really well.

They had a great reputation for being awesome at that thing, that function, whether that's demand generation, enterprise sales, whatever that is. And they're coming into a new situation expecting to just apply that playbook. And oftentimes they're recruited because of that playbook. They did X super well at well-named company and they kind of come in thinking, this is what I'm hired to do.

I'm going to take that and I'm going to apply it in this situation. And what they don't do is pause and really understand like who's the team around me. Is this the right playbook? Are all the plays applicable? What else might I not know about the situation about these customers? Sometimes it's a slightly different customer profile.

And just that nuance, you know, can really affect a go to market leader. This may sound like totally settled, but if they've built a great sales organization that sells into sales leaders, and now they have to sell to marketers, or they have to sell to customer support leaders and they don't pause to kind of learn the new customer profile.

There's many of those where it's like, okay, I'm going to repeat what I'm great at, where there's the highest likelihood of failure. 

[00:16:43] So, how does that inform the way that you evaluate executives now versus maybe before you learn this lesson? 

[00:16:51] Yeah. I spend a lot of time more in conversation and seeing how they would approach the very real problems and challenges that the company is dealing with.

And just also a lot of it is actually seeing what questions they have and how thoughtful those questions are. Are they really asking the questions in the sense that they're thinking about? What would I do in this role? Are they starting to picture themselves in the company in the role? It makes a huge difference.

The people who are, and they're genuinely interested, their questions are just different. Their questions are as if they're already on the team versus. I would say maybe more of the superficial questions that you would ask more from like a financial investor lens, growth rate competition threats. Yes. You should ask about those things.

You should get smart about those things, for example. Okay. Good questions I've gotten before is helped me understand some of the most important customers. What do they look like? What was the last thing they shared that they really love about working with this company or the product and what's feedback that they've given of what they don't like and what would cause them to leave people who are really starting to think about, Hey, if I were part of running this business, what would I need to know?

What would I want to know so that I can make the biggest impact as fast as possible. Those questions just are very different. 

[00:18:17] So, if you think about your own journey and you think about you had a playbook and a set of frameworks and org structures, and what have you in your role at Zendesk, and then you went to guru and I'm sure to your point, there are some elements that are transferable.

And some that aren't, they're kind of in adjacent businesses. How would you describe how the playbook was updated for guru or what are the principles that applied from your Zendesk experience and what are the principles that had to be thrown away and sort of rewritten. The 

[00:18:48] things that are broadly applicable are just understanding that different stages just the organization goes through.

And I think what I brought from Zandesk degree was more of the perspective and the experiences to be able to help the team have context on why certain things were happening at certain times. I know that sounds kind of vague. I had a number of conversations, both at guru, at a sauna at SendGrid around like what growth actually feels like on the inside and why it feels much harder than the stories that are written about high growth companies from the outside.

So I think that the context. Is something that I've found that I can bring, which is, Hey, different parts of the organization are going to grow at different rates. And that is natural, but there's some side effects that causes, right. There's going to be teams. Oftentimes they're the ops teams or the support teams that just are gonna feel more stretched and feel like things are breaking every day.

And they're going to look at some of peer organizations that feel like they're getting funded faster, and that's just a natural, all teams don't grow at the same rate at different stages. So giving people context and then saying, okay, for our company and team. What are the most important things that we get right, right now, from now until the next milestone and what are the things that we can allow to run a little hot or feel like they're a little bit breaking at the edges, but it's not going to fundamentally cripple our ability to be successful until the next milestone.

So those are just questions that we can then ask as a team and answer for ourselves versus saying, Hey, sales and marketing should always be funded and support should run lean. That's not a universal depending on your business. Right. But the concept of some teams growing faster than others is applicable and gives people context.

[00:20:50] So, can you give a few more examples of the things that you find to that point that are similar? Because you have a great set of experiences across both consumer and enterprise in different roles at different scales, and then the watching businesses from the board perspective.

And so those categories of things, or the framework that you think is broadly applicable versus maybe a story or two about some of the things that you learned and worked at one company and didn't work at another, 

[00:21:17] the applicable ones for at least in my experience, go back to team and culture and values and making sure, you know, the leadership team founders are spending time really invested in values and culture and talking about it, reinforcing it, evaluating it, making sure it works for every employee, no matter how long they've been at that company and that the system of values and the culture that's being.

Reinforced as well as like grown and adapted helps every person make great decisions and make the team better. And then the specific values, how they're worded, how they're prioritized are going to be unique in each organization. But I've definitely seen it no matter what stage, whether you have 10 people or 5,000 investing that time and energy into your team, the values and culture is so, so, so critical.

And so I would say like, that's something that's been applicable across every team I've worked with. Then there's things more, I would say like around business model and go to market that really are going to be different just because a company is a SAS company doesn't mean that it's going to have all the same attributes as any other SAS company.

I mean, just the three I'm on boards of are all in the category of SAS, but they're all very different. Isana has both a self-serve and light touch motion as well as an enterprise. And they've got expansion, like that's really the business model Gusto just serves as and BS. So that's a very different SAS go to market model.

And then patriarch has got combination of sort of a SAS business model for their creators, but then also a marketplace aspect to it with patrons. And so, yes, they're all in the category of SAS, but the actual go to market strategies and tactics and how you test that are very unique. And so. Have to be applicable specifically to that business and that stage and what's ahead.

And then knowing that sort of diving into each company, it's then focusing on like, okay, what's of all the things the leadership team could be spending time on what really are just the couple, most critical that are going to make the difference. I think that's also something just asking those questions has been really important in any situation that I'm in, because there's always more priorities and always more things that people could be doing then there's actual resources and time, no matter what size company.

[00:23:57] you think about executives making transitions from one company to another, and maybe you think about your own last transition, what is a great first three, six months look like? What should you be doing as an incoming executive to increase the probability that you'll have success there? 

[00:24:13] I'm a huge believer in very transparent, 30, 60, 90 day plans.

And in fact, I think good interview processes actually transitioned into developing those 30, 60, 90 plans really naturally. So like, if you have done a good job, finding the right person and having good conversations, those conversations naturally lead to like, okay, what are the outcomes that this person is going to drive in their first 90 days in their role, especially as a leader.

And so for me in diving into any new role, it's what are the outcomes I'm looking to drive with the team around the business? For the first 30, 60, 90 days. And what are the team outcomes, culture, building the team, maybe understanding current team and talent and helping them achieve their professional goals.

And then with a 30, 60, 90 day plan leaving room in there for the learning. So who are the customers I should be spending time with to really understand and listen to what they love and what they wish we were doing differently. Really getting to know all aspects of the team, not just the team that I'm directly responsible for.

So spending lots of time across the organization at every level, and then really understanding the metrics deeply. I think that's critical for, again, any role. Oftentimes people will come into a role and just look at the metrics for their function, but I think good leaders should look at all the most critical metrics across the business to understand where there's the biggest opportunities for improvement and where are the superpowers of that particular business.

And then laying that out. There's lots of great templates out there and I'm sure people have adapted their own, but I like one where it's just really clear where it's like, these are the things that I'm working on. These are the people I'm meeting. And then these are maybe the projects or initiatives that I'm going to be a part of, making sure really land in this period of time.

Keeping it as a draft. And sending it around and asking for input again, from everybody on the team, not just direct reports, not just the founder CEO, but making it open depending on the size of the organization. It could just be everyone in that reports up to you. If it's a small enough company, it could be every employee and getting their feedback and both for myself and people that I've hired be a really, really good way to de-risk the first 90 days and make sure the leader's making an impact.

Make sure they're having the right conversations and make sure that other people have a vested interest in their success. That's the other thing, oftentimes when leaders come into organizations, whether we intend it or not, a lot of people are, have a wait and see we're excited about them, but is this going to work out?

And that comes from past failures, way back in my E-bay days, there used to be a term people would use for new execs, which was like hero to zero. How fast is someone going to go from hero to zero? Because people were kind of waiting and seeing if they were going to be successful versus like everyone should have a vested interest in helping to make that person successful.

[00:27:22] get people to behave or act like that other than just saying. Hey, we need to take a vested interest in this new VP of this or SVP of 

[00:27:29] that. Yeah, definitely is easier said than done, right? When there's lots of everybody has their own 

[00:27:35] well. So maybe even backing up to the interview process.

I do think it begins there. I firmly firmly believe that no one should meet their new boss on their first day of the bosses job. That's just such a terrible experience. And so it doesn't mean necessarily that every single person has veto power, but I absolutely believe that any direct report has to be part of the interview process and ideally the whole.

Functional team in some form or other. And that might be group presentation that might be lunch and learn what I like to do with the team. If they're not part of the group that's been designated as a final interview team, that gives feedback. I like to ask people for feedback on two fronts, like what they would be excited about with the new leader and what they're concerned about, and then sharing all of that feedback with the person you hire.

So this is what the team's really excited about all around. They're so excited. You're going to bring these things to the team. Here's what the team was concerned about and may just be like, Hey, we didn't learn this about the person or in their last role. They didn't have responsibility for this. Kind of team or function and the concerns then become, you can do a risk mitigation plan for those great.

These are the concerns. This is how we're going to address the concerns, but just that participation in the interview process, I think, starts to create that vested interest of the team of making the person successful. And then the participation in the 30, 60, 90 day plan, right? Giving input, seeing output, seeing updates on their 30, 60, 90, then it becomes less of a wait and see, like I'm sitting on the sidelines, seeing if this person is going to be successful.

If I have an active part in giving them feedback, if I have an active part in identifying potential risks, as well as an active part in identifying the things that I'm excited that they're bringing, it just feels a lot different than having sort of a new person, a shiny as they are show up. 

Today's episode is with Anne Raimondi, Chief Customer Officer at Guru, a knowledge management platform. Across her career in tech, Anne has been a founder, operator, executive and an independent board member at companies like eBay, SurveyMonkey, Zendesk, TaskRabbit, Asana and Gusto. In addition to her most critical leadership lessons for scaling up as an executive, Anne dives into her playbook for building impactful boards.