Across her impressive career in tech, Anne Raimondi’s trajectory includes pit stops at some of the most interesting companies around. She was part of the founding team at Blue Nile during the dot-com boom. She then worked on the product marketing side at eBay amid its rapid growth. After leading product marketing at SurveyMonkey when it was just 30 employees, she started a company that was acquired by TaskRabbit, where she took on the Chief Revenue Officer role. In her next move, she shifted to operations as an SVP at Zendesk. Now the Chief Customer Officer at Guru, she’s also built up an impressive track record as a board member at companies like Gusto, Patreon and Asana. She even takes her talents to the classroom as a lecturer at Stanford’s Graduate School of Business
But what stands out on Raimondi’s stacked resume isn’t just the calibre of companies she’s had a hand in growing, but the ground she’s covered along the way. She’s seen startups from every altitude — from PM to VP, from founder to board member. She’s tackled consumer and enterprise challenges at every step of the startup growth journey. Even her functional expertise is tough to pin down — she’s headed up product, marketing, revenue and operations.
She’s also deeply thoughtful about what makes teams tick — check out her insanely-helpful “trust equation” that she’s previously shared here on the pages of the Review. So who better to turn to than Raimondi for an inside look at how to make startups’ C-Suites and board rooms more effective? From the key ingredients for a high-functioning executive team, to preparing the folks already within a company’s ranks to take their own seat at the table, Raimondi’s clearly crystallized the lessons and stumbles from each chapter of her career — with a healthy dose of modesty. “Great leaders and executives have enough humility to recognize, ‘I was on a rocket ship, and these are the mistakes I made on that rocket ship that I wouldn’t do again,” she says.
In this exclusive interview, Raimondi doles out spot-on advice for founders, executives and board members looking to level up their leadership frameworks — and for folks who someday hope to step into these same shoes. For execs, she sketches out how she approaches career transitions, and how to sidestep the traps new execs commonly fall into. For founders, Raimondi also opens up her hiring playbook for spotting your next great executive hire and developing the internal folks eager to take on more. For board members and CEOs, she outlines the tested tactics that power the most effective boards. Let's dive in.
FOR EXECS — INVEST IN HUMILITY AND CURIOSITY.
In an industry that loves a good hack, framework, or nugget of career advice that can be distilled into a quick Twitter thread, Raimondi recommends resisting this impulse. “The most successful executives are adaptable — meaning that they’re successful in multiple places and multiple settings, not just at one brand-name company. They stay curious and while they might have a ton of amazing applicable experience, they don’t come into a situation trying to apply a playbook,” she says.
It means a return, again and again, to first principles thinking. “This humility starts with, in many cases, 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. How do I fill the gaps that I have? How do I go seek outside help or help from my board and investors? How do I re-imagine how I'm running a certain team, everything from how I'm doing my one-on-ones and leading my team meetings,” says Raimondi.
To get more tactical here, she implores you to actively seek feedback — and avoid faking-it-til-you-make-it. “That's a critical part of humility. I'm figuring this out, and so I need people to really be critical of me and help me see the gaps. That's what I've seen in the most successful execs who can truly scale,” she says.
That humble streak extends to how the most impactful execs interact with the whole C-Suite.
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’s what differentiates the best executives where they're truly a team player — they care about the whole business, even if they're just responsible for marketing or sales or product.
“It also allows them to not just stay in that lane, but to take on whatever the next important initiative is for the company,” says Raimondi.
FOR EXECS — HERE’S HOW TO FIND YOUR FIT.
Of course, scaling up as an impactful executive starts with finding the right company fit. No square peg will fit into a round hole — regardless of how spectacular the square peg is. When folks come to her for advice on how to narrow in on their next career move, she points them to three key areas.
- Company mission: “Sometimes I’ll talk to people who say, ‘These are the companies on my target list.’ And I’ll ask, ‘Tell me why you’re excited about each of these companies.’ A lot of times the answer is, ‘Well, they have a good brand name and they’re growing really fast,’” says Raimondi. “You don’t have to be the product’s target customer, but it’s important to be intellectually interested, to wake up in the morning and be really excited about the problem set that you’re spending the majority of your day on.”
- Growth and impact: “This isn’t about being so wedded to a specific title, but how will this role challenge you? It could be the particular role, or the company stage is something different than you’ve worked in before.”
- Team: “This is absolutely the most important category. Who are the people around you? Who will you be working with? Frankly, the people around us change us for good or worse. I’ve seen people that skip over this third category even if they have a feeling that team fit isn’t quite there, but it checks the boxes for the other two criteria. Inevitably, they end up unhappy.”
To further suss out fit, especially for execs who are interviewing with the CEO, Raimondi flags three areas for concern.
- Turnover: “I do think they should be able to have an open conversation about other leaders who have left. If the person can’t have an honest conversation about leadership turnover with enough specificity, depth and reflection — especially if they’re regretted attrition — that’s certainly a flag that the CEO hasn’t learned from past experience. If every situation is someone else’s fault, that’s a giant flag.”
- Roadmap: “Especially if it’s a first-time founder, they may be hiring for a role that no one else has had, so they don’t have the perfect job description or all the objectives. But it shouldn’t be so vague — there should be a point of view. It’s a flag if you sense that they haven’t actually paused and thought about outcomes, or taken the time to research what those outcomes might look like. It signals that expectations are going to be all over the place.”
- Feedback: “Especially for CEOs, do they want your feedback? Have they sought it out during the interview process? When I talk to friends or colleagues who have gone to a startup and been super excited about it, but it didn’t work out, it was because the relationship with the CEO-founder wasn’t a two-way street. Really good, experienced executives expect to be able to give and listen to feedback.”
FOR FOUNDERS — HOW TO NAIL EXECUTIVE TRANSITIONS.
Whether they’re stepping into an existing pair of shoes or carving out a brand-new role, new startup leaders often face a dose of skepticism. “Whether we intend it or not, a lot of people have a wait-and-see approach. We're excited about them, but is this going to work out? People often wait and see versus having a vested interest in helping make that person successful,” says Raimondi.
Way back in my eBay days there used to be a term people would use for new execs, which was hero-to-zero. How fast is a new exec going to go from hero to zero?
To shore new leaders up with firmer footing, Raimondi takes it back to the interview process. “I firmly believe that no one should meet their new boss on their first day of the boss's job. That's such a terrible experience,” she says.
There may not be time to squeeze in 1:1s with each team member, but fitting in a group presentation or even a lunch-and-learn is critical to start building trust and avoiding the hero-to-zero trap. “It doesn't mean that every single person has veto power. But I absolutely believe that any direct report has to be part of the interview process,” she says. In these forums, Raimondi likes to ask people for feedback on two fronts: What they would be excited about with the new leader, and what they're concerned about.
Next, connect the dots between the new hire and their team. “Share all of that feedback with the person you hire. ‘This is what the team's really excited — you're going to bring these things to the team. And here's what the team was concerned about,'” she says. “It may just be, ‘We didn't learn X about the person, or in their last role, they didn't have responsibility for Y.’ And then you can do a risk mitigation plan for those areas,” she says.
“Giving input, seeing output and getting updates on their progress — then it becomes less of a wait-and-see, sitting on the sidelines evaluating if this person's going to be successful. If I have an active part in giving them feedback, 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,” she says.
FOR EXECS — AVOID THESE ONBOARDING STUMBLES.
Turning her advice to incoming execs, Raimondi maps out three common pitfalls that keep you trapped in hero-to-zero dynamics.
Pitfall #1: Jam-packing your first 3 months and ignoring quick wins.
After signing on to officially climb aboard a startup, it’s time to start putting pen to paper. “I'm a huge believer in very transparent 30, 60, 90-day plans. 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 that, ‘These are the things that I'm working on, these are the people I'm meeting, and then these are the projects or initiatives that I'm going to be a part of,’” says Raimondi.
There’s often an urge to be really ambitious here and hit the ground running, but she’s seen too many folks jam-pack their 90-day plans without leaving room for learning. “Who are the customers I should be spending time with to understand and listen to what they love and what they wish we were doing differently? It’s about getting to know all aspects of the team, not just the team that I'm directly responsible for as an exec,” she says.
Next, put on some noise-cancelling headphones and dive deep into the analytics dashboard. “Deeply understanding the metrics is critical for any role. Oftentimes, people will come into a role and just look at the metrics for their function, but good leaders look at all the most critical metrics across the business to understand where there's the biggest opportunities for improvement and what are the superpowers of that particular business,” she says.
On top of leaving space for listening and learning and diving into countless spreadsheets, keep your eyes peeled for some quick-win opportunities — bonus points if they’ve got plenty of collaboration touchpoints. “Almost all of it's going to be situational to the person's role, the team and organization, but make sure you have quick wins in your 30, 60, 90. What's actually doable, what's measurable and then — probably most important — what gives people a real opportunity to work together with you? The best way to build good bonds and de-risk is to work with someone in action on an important project or initiative,” says Raimondi.
Here’s her advice for spotting these quick-wins that move the needle. “They're in that category of ‘No one currently owns this and we think we need to do it.’ Sometimes just picking up one of those opportunities and showing people how you work, and your quality of work, can be really powerful in terms of building trusted relationships, as well as making an impact,” she says.
Her final piece of advice here? Don’t be too protective of the plan you’ve put together — you only get one first impression. “Keep it as a draft and send it around, asking for input from everybody on the team — not just direct reports, not just the CEO. Depending on the size of the organization, it could be open to everyone who reports up to you. If it's a small enough company, it could be every employee. For myself and people that I've hired it’s been a good way to de-risk the first 90 days and make sure the leader's making an impact,” says Raimondi.
Pitfall #2: Sticking to the same playbook.
Brand-new execs may not have total control over how much the new team embraces them — especially when there’s existing scar tissue from past mis-hires. But over the course of her career, Raimondi’s seen plenty of well-meaning folks stumble out of the gate. “Some that I've seen high failure around is that the exec has been exceptionally successful at their last place. They built something that worked really well — whether that's demand generation, or an enterprise sales motion, and they're coming into a new situation expecting to just apply that playbook. And what they don't do is pause and really understand, who's the team around me? What else might I not know about the situation about these customers?” she says.
Is this the right playbook and are all the plays applicable?
“Oftentimes they're recruited because of that playbook — they did X super well at a big-name company — and they come in thinking, ‘This is what I'm hired to do.’ But there’s a lot of nuance within startups, and it can really affect a go-to-market leader. This may sound subtle, but if they've built a great sales organization that sells into sales leaders and now they have to sell to marketers or customer support leaders, they’re in trouble if they don't pause to learn the new customer profile,” says Raimondi.
Pitfall #3: Skipping over the good.
Another misfire from new execs itching to make an impact? Skipping over all the good and laser-focusing on what needs work. “You're joining an existing team, and every team has its strengths and its opportunities — some are going to be healthier than others. For many executives, you're brought in because there's something that needs improving on the team. There's some dynamic that needs improvement for that next leg of the journey. The bar needs to be set at a different level,” she says.
If the company leadership operates a transparent interview process, most of these challenges will have already surfaced. “If you're a C-level exec coming in, you're going to have already spent time with a CEO, as well with board members. Through that process, oftentimes people are pretty open about sharing what the challenges are. The key is continuing to stay clear-headed and see some of it for yourself, too. The pitfall to avoid is essentially gossip. Starting with, ‘Well, I heard this about so-and-so’ — that's not helpful,” she says.
If you skip over all the goodness, you quickly lose trust or become known as the person who’s only seeing everything that’s broken.
FOR FOUNDERS: HOW TO SPOT THE BEST TALENT — EXTERNALLY AND INTERNALLY.
Raimondi’s been on many hiring loops for open exec roles, and of course, gone through the process herself several times. “Another key trait of great leaders is being confident that 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,” she says.
But in-demand folks have plenty of options. Here’s how Raimondi approaches nabbing the best hires. “Really talented people have so much choice. People who've worked with them before are trying to recruit them and they have opportunities to start their own thing. It’s key to understand what's going to be interesting, exciting and a growth opportunity for somebody that then fits with what the company can provide,” she says. “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. Same flip side for people who are functional experts and have demonstrated that they can build from the ground-up and now are really interested in an opportunity to scale.”
Her goal on aligning these challenges and growth opportunities? No surprises. “Every company has its challenges. Being really honest about what those challenges are — and making sure those are the challenges that someone's excited about solving — creates the best opportunity for people to thrive,” says Raimondi.
During the interview process, she’s on the lookout for three key ingredients:
- Perspective. “I spend a lot of time seeing how a candidate would approach the very real problems and challenges that the company is dealing with. Are they starting to picture themselves actually in the company and in the role? A lot of that is actually seeing what questions they have and how thoughtful those questions are,” she says. “The people who are genuinely interested in the role ask questions as if they're already on the team. It’s the difference between just asking more of the superficial questions from a financial investor lens — growth rate, competition threats — versus ‘Help me understand some of the most important customers, what do they look like?’”
- Stumbles. “When you're interviewing executives, if they can't honestly talk about mistakes, that's another sign that they might not be a good fit. I don't know a single great executive or leader who hasn't made mistakes that they are happy to unpack and talk to you about.”
- Humility. “Great candidates will say, ‘Oh, the best thing I did was bring this other person on because I learned so much from them.’ How they talk about success is often broader than themselves. All the work in the knowledge economy is team-based and it's people-based. I find that great leaders will talk about their experience by bringing in the teams that they are a part of — we learned this and these are some of the things we tried versus I did this and I made this happen.
And if you're a CEO-founder who's hiring for a brand-new role, it's time to pull in some reinforcements. "You as the CEO should still interview the candidate for values and behavior fit, for how well you'll be able to communicate and solve hard problems together and for how passionate they are about the company you're building," she says. "But it's okay to ask someone who is a great CMO to interview CMO candidates. And for candidates, this practice communicates a seriousness and thoughtfulness about the function, even if you're still learning as a founder."
Mining internal talent for your next generation of leadership.
But hiring new talent and bringing them into the fold is just one piece of the puzzle. The best leaders have a nose for internal folks who have more in the tank. “Whether it's going from Series D to Series E or whether it's preparing to be a public company, I don’t think the only answer is bringing in someone from the outside. With one of the companies I’m working with, there was a conversation around executives and if we're planning to be a public company in the future, do we need to start looking for a C-level exec who's been part of a public company?” says Raimondi. “But it's not an either or. There’s a really talented person on the team who's doing the role today, who has raised their hand to say that they want to stay in the role, but is also very self-aware that it's the biggest role they’ve ever been in.”
To calibrate whether the employee is ready for the next step on the executive ladder, the company partnered with an outside firm for an in-depth leadership assessment, which includes external benchmarking for the role, 360 interviews, and conversations with the board about expectations. “What it will give us is basically a roadmap to say if this person were to continue growing in this role over the next couple of years, where are the biggest development areas? And how easy or hard is it to move the needle for those development areas?” she says.
Even if the final assessment is that the team member isn’t quite ready to step into those shoes, it’s a worthwhile exercise that uncovers a few key insights. “It allows us to have an honest conversation with the person and they get a roadmap on development, which is awesome. And it can also open up the possibility of hiring a very different profile person from the outside. Someone we can be honest and say ‘Hey, there's a great person on the team already. They have ambition to take on this role and grow into this role over time. We want to find someone who's super excited about that.’” she says. “Maybe this is the last C-level role they want to take, and they want to be able to groom someone — that type of candidate might be better than bringing on someone who caps the development of the person we already have on the team.”
Raimondi’s got a strong passion for folks who are excited to step out of their comfort zone, because she’s done the same in her own career. “When I took on people operations at Zendesk, I'd never run that function before. Mikkel Svane, the CEO, was super generous and introduced me to a woman named Nancy Connery, who runs an HR and talent consulting organization. She was an expert at a function I'd never run before and she signed up to be a resource for me throughout my journey. There's things that you can do to help support someone's growth, instead of just telling them that they haven't done it before, or they're not ready,” she says.
It's really hard for any human to grow their skills and capabilities at 100% year over year. I think the fastest rate of growth for humans is from age zero to one.
FOR MORE EFFECTIVE BOARDS: IMPLEMENT THESE HEALTHY HABITS.
Raimondi took on her first board member post a decade ago. Along the way, she’s found that sinking into a steady rhythm as a board member has required suppressing some of her basic instincts. “As an operator board member, hear this advice: You’re not there to operate,” she says.
Great operators often will go into solution mode, but good board members are more often quiet than they are talking.
“You’re actually there to ask critical questions. You’re representing the shareholders and ensuring that the leadership team is building an enduring company in a sustainable way. You’re learning about the business, what the key issues are, and the different perspectives of the other people on the team, or around the board room table,” she says.
And just as she’s carefully honed her process for transitioning into a new executive role, Raimondi also comes into each board position ready to be a sponge. “I love asking existing board members their thoughts on what's working really well. Where are the opportunities for growth? What's that one thing they would like to see change?” she says. “I like asking, especially as boards evolve, what works with the format of the board meeting itself? Because oftentimes as the first independent board member at a number of the companies I'm working with, the company is growing into a new set board interactions. Oftentimes the company has outgrown how they're doing board meetings, but they haven't updated it yet.”
As a new board member, on top of her individual meetings with the CEO and fellow board members, she gets time on the calendar with a wide range of folks. “I personally like to spend time 1:1 not only with the CEO, but with the other leaders and with frontline employees in different departments. It helps me get a better, deeper, rounded view of the business. It’s all in the spirit of the more context that I have, the more relevant and better the critical questions that I can ask to help ensure that the company is growing in a healthy way,” she says.
Currently, Raimondi sits on the boards at Gusto, Patreon and Asana (where she’s the lead independent board member), and previously sat on the boards for ThredUp and SendGrid — each with its own unique set of roadblocks in its path. But across these disparate challenges, Raimondi’s seen a number of common best practices that she recommends any board or CEO implement.
Habit #1: Stop being polite and start getting real with your discussion topics.
“From a pre-public company perspective, if you're spending a lot of your board meeting doing just updates and readouts, you're probably not getting the most out of that time. You should be digging in on the decisions that are the messiest ones,” says Raimondi.
Too often I see founders that have a lens to the next round of fundraising, so they want to show that everything’s going well. But there’s always something that’s hard at a high-growth startup. No matter how lovely it looks on the outside, on the inside it’s hard work.
Raimondi lays out a few hurdles that are worth your board sinking their teeth into. “It could be strategic roadmap decisions. You might have multiple customer segments and some are performing on some metrics better than others. If that's not discussed at a board meeting, you're missing out on an opportunity to get really smart people who have a vested interest in your business being successful to dig in,” she says.
Here’s how to lay the groundwork so that in-person time packs a punch. “If it's not a significant decision or if something's not significantly off track, those should be more like pre-reads. You should be spending in-person time on meaty topics. Frame the conversation by asking your board members to do some pre-reading and homework ahead of time on that topic to come informed and ready to have a conversation. That’s the most fruitful, instead of a stream of functional updates that they could read asynchronously,” she says.
Habit #2: Add a personal narrative for a peek behind the curtain.
When it comes to crafting a pre-read that drives value and feels less like homework, Raimondi’s seen a few different CEOs deploy a personal touch. “I’ve worked with many CEOs who write a board letter in advance of the board meeting, which is a narrative just from their perspective. Some are longer than others, but it’s almost like a voiceover for the deck — what's on their mind,” she says.
The best board letters include what the CEO is most proud of and excited about over the last quarter, but most importantly, what’s keeping the CEO up at night. “That in particular is so important for the board to know. What is the most critical issue that's preventing them from getting good sleep?” she says. “Then yes, you still get the deck and pre-read, but it gives you context around where we really need to spend time. CEOs who were open and honest in these relatively succinct letters changed the conversation with the board.”
And when a particularly thorny issue is on the docket, Raimondi recommends CEOs carve out time for individual meetings with each board member. “A number of CEOs I work with will do either board debriefs or board pre-conversations, especially if there's something big or strategic that they're working through. They'll spend time 1:1 just to make sure they're hearing everybody's perspective, but then they’ll circle back and ensure that context from those 1:1s is shared with the whole board, so it doesn't feel like they're having different conversations with different people,” she says.
It’s a critical skill for CEOs to treat your board as its own high-functioning team.
Habit #3: Implement closed sessions and feedback loops for board harmony.
To keep finely tuning your board, she recommends getting a board-only session on the calendar where everyone can speak frankly. “I think all boards should have a closed session without the CEO. And then most importantly, have a feedback loop from that closed session, where everything gets relayed back to the CEO. This habit can be life-changing for everybody, because often there are all these unsaid things from everybody's perspective,” says Raimondi.
She lays out a few wrinkles this process smooths over — from both sides of the table. “The CEO and their team can get frustrated when the board deck is like 70 pages and they only get three comments. They've spent a whole week getting ready for a board meeting and putting this beautiful deck together instead of running the business. And then they're like, ‘Okay, we got three mildly helpful comments that we probably could have gotten without putting 70-100 pages together,” she says.
But the friction doesn’t stop there. “Then there's frustration sometimes from the board perspective where it's like, ‘Hey, it doesn't feel like we're talking about the right things, it doesn't feel like we're spending enough time on strategy.’ But they don't get fixed unless everybody's sharing that,” she says.
“That's a good habit that can make a huge difference in the quality of conversation and then the strength of relationships, because the stronger the relationships are, the easier it is to have the difficult conversations. If you don't have that foundation, then the sticky conversations around, ‘Hey, is this exec really working out? Are they delivering what you had expected?’ are often skirted around until it's too late. Telling the CEO, ‘You have to fire that person,’ shouldn't be the first conversation you have with a leader about someone on their team,” says Raimondi.
Not only does it bring laser-focus to the topics most worth the board's time, it creates the repetitions needed to build that feedback muscle. “Everyone just gets better at being direct — I like this, I don't like that. Could we try something new? I'm a product manager at heart, so I think of it as applying a sprint retro to your board meeting. What's working, what's not working. What's something we want to try?” she says.
This article is a lightly-edited summary of Anne Raimondi's appearance on our new podcast, "In Depth." If you haven't listened to our show yet, be sure to check it out here.
Cover photo by Getty Images / HStocks.