Ep. 75 – Integrate Your Core Values With Allison Pickens

Values need not just be posters in your office walls. How can you integrate them into your decision-making process? Let us get the answers from Allison Pickens, COO at Gainsight. She is an international speaker, blogger, and host of The Customer Success Podcast. In this episode, she talks about how your role models help develop you as a leader. She also shares her insights on hiring energized employees and how to retain that energy within their roles. Allison dives into a company’s core values and its importance of being infused into the day-to-day company and personal life.


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Allison Pickens, Chief Operating Officer of Gainsight. She is an internationally known thought leader on driving subscription revenue and scaling teams. Allison was named one of Fortune’s Most Powerful Women. One of the top women in SaaS, the top 50 people in the Sales and Business Development industry and a top customer service influencer. She’s an international speaker, blogger and the host of The Customer Success Podcast with over 100,000 plus listeners for over two seasons. She has a passion for working with companies to scale their go-to-market operations and create an exceptional customer success initiative. Allison has a BA in Ethics, Politics and Economics from Yale University, as well as an MBA from Stanford University. On weekends, you can typically find Allison contemplating Political Philosophical questions while on a hike in the Marin Headlands, a beautiful area to be hiking in. Allison, welcome to the Second in Command Podcast.

Thanks for having me.

You were one of the smart people. I was one of the dumb people. Growing up in school, did you know that you were going to get into leadership? I was always told to be a lawyer. Were you positioned the same way?

A lot of us are probably encouraged by our parents to pursue a more conventional career path. I did not think that I would be a leader when I was younger. In second grade we were given an assignment to draw a picture of ourselves at some point in the job that we were going to have. The job that I envisioned for myself was running an ice cream shop since ice cream was my favorite thing. I had not so grand aspirations at the time, although I still want to run an ice cream shop someday. The real reason that I got interested in leadership, although I didn’t quite recognize it at a young age was that I had great examples of leadership in my family. My father is a big history buff. He’s read virtually every biography of a leader in the American Government since inception and other governments as well.

I would always hear stories about difficult decisions that leaders had to make. I would hear inspirational speeches that he would recite. I would hear passages from books that he was reading. I always found them inspiring. My mom’s side of the family, my grandparents and extended family were deeply affected by the holocaust and other religious persecution or political persecution. I always deeply admired the perseverance that they had, a perpetually positive outlook. That, coupled with the examples of servant leadership that my dad talked about has always made me feel as though it’s possible to do great things in the world and can get back to others.

I love the impact that they had on you and you still remember that too. I love that you even started with that because so many people don’t even go there right away. What do you think your mom or father would say, what area do they think that they’re the proudest of that you have taken from them, but have used in your business career?

Our values are important in my family. Integrity and honesty were always the most important things that were emphasized. I’ll tell you another story from my childhood. When I was three years old, I was playing a game of Uno with my mom. You might remember that card game, Uno. She was cooking dinner simultaneously. At one point she got up to check on the stove. I had in front of me the whole deck of cards. I thought I was clever. I decided to stack the deck so that I would get all wild cards when she dealt with our hands. Being three years old, I was proud of myself. She eventually came back, dealt out the cards and realized as I was playing my cards that I had a hand of all wild cards, which is statistically improbable.

When she realized this, she looked at me and said, “I don’t play with cheaters,” and left the game. I was left to mull over the moral failure that I was at the time. That was an incredible lesson for me. It’s one of my earliest memories. My mom is certainly a strong person, a loving mother and she did it from a place of love. What I especially remember coming from that incident was that it’s different from being smart versus to do the right thing. I still carry that with me in business. I’m always looking to do the right thing and honesty continues to be a big value of mine.

I want you to tell us a little bit about Gainsight so we know some perspective of the company you’re running. I want to dive into some stuff around values and I want to go backward in your career a little bit.

Gainsight is a software and service company for SaaS companies. We’re venture-backed. We have about 650 people worldwide. We have softwares that helps your entire company become more customer-centric. We have multiple products that allow you to gather a source of truth on what’s going on in your client relationship, drive revenue growth and retention from your existing client base over time. In general, we work with B2B subscription companies that are looking to drive stronger retention and growth and their install base of revenue.

The team that you run, that 650 people worldwide, what part of the org chart flows into you? What part flows into the CEO?

The COO tends to be one of the most ambiguous functions or titles, given that it can mean a lot of different things. In my case, I’m generally responsible for strategy and execution across our business. We have a cadence of setting goals and ensuring that we’re meeting them as well as reflecting on our progress that we call the rhythm of the business. That spans the whole company. There’s also a section of our company, that solid line reporting to me, which includes all of our post-sale functions. My previous role was Chief Customer Officer at Gainsight and I promoted someone to take on that role. That organization still reports to me. That includes customer success management, professional services, customer support and the operation supporting those groups.

All those roles up to the Chief Customer Officer are reporting to me. I also run a corporate development which is our build, buy, partner strategy M&A. I run business development, which is partnerships and alliances, business operations, which is the strategic and executional glue across our company, as well as customer engineering. I also run a group of engineers and product managers who are focused on automation across our customer journey. Finally, there’s a business that I’ve acquired. It used to be called Aptrinsic, today it’s called Gainsight PX for product experience. I generally manage that part of our business, on a dotted line perspective.

You’ve got a ton on your plate right now. You did your MBA at Stanford. If you go back to your MBA, what do you think are the core skills that you’ve pulled from there that you’re using today? If you had to pick one or two.

People go to business school for a variety of reasons. In my case, the jobs that I’ve had before business school at BCG Boston Consulting Group and Bain Capital were boot camps for learning about building models and learning how to design a strategy. I came to business school with the hopes of learning those soft skills, but that makes them seem more trivial. At Stanford, in business school, they take it seriously helping to give you experiences that help you build those leadership capabilities and of course the community that you build in that environment is strong as well.

In particular, there was a program at Stanford Business School called Leadership Fellows. In which you go through a series of different courses starting with a course on interpersonal dynamics, which is fondly known as touchy-feely. You learn through deep interactions with other classmates how you are perceived and how your actions affect emotions in others, which in turn allows you to improve your communication and presence. From there as a second-year, you mentor first-year students in their leadership and generally in their personal professional growth. That program, in particular, was a great asset.

That would be a massive one in terms of coaching and developing people and then also learning about yourself. Is it like Leadership and Self-Deception, have you read that book?

I haven’t but maybe I’ll add it to my list.

It sounds like that might be where it is. It’s where we think we’re being perceived and how we’re being perceived. Then once we gain that introspection and emotional intelligence around it, we can show up a little differently. Even showing up as our true selves and then understanding how to communicate that we’re going to be that way.

I notice in my current work environment as well that people might have a certain intention. That intention isn’t always conveyed through the way that they communicate their actions or at least the way it lands on other people. What that course focuses on is helping you correctly match your communication style with your intentions about the effect on other people that you desire.

SIC 75 | Gainsight COO, Allison Pickens

Gainsight COO, Allison Pickens: The COO tends to be one of the most ambiguous functions or titles since it can mean a lot of things, like being responsible for strategy and execution across the business.


When you’re recruiting, what are you looking for as a core? I know it’s a massive generalization. If you’re trying to bring in future leaders into the company versus a frontline staff, are there any core traits, behavioral traits versus skills that you look for?

I’ll start by saying that in general. Whenever I have an open role, I’m looking to not only fill that role from the perspective of a particular set of skills that I’d like for that role to exhibit. I’m looking to leverage that open headcount to create an even richer and more cohesive team. Often, we think of roles as being siloed. There’s a certain criterion set that we have for that particular role. We need to find the best match or the A player for that particular role. A better question is, how you can leverage that goal to create a team that you’d call an A+ Team.

For example, if you’re in a work environment where you have a lot of people with a strong analytical skillset, technical skillset. For whatever reason, those particular folks don’t have a particularly collaborative sense. You might leverage an open headcount to hire someone who’s particularly collaborative and likes to create ties across those people. That way, everyone on the team improves their performance, as a result of that new hire.

I had this weird, strange flashback to the University and high school where I used to play volleyball. I remember this one guy that we brought on to the team, who was an amazing setter. We had three of us that were big power hitters and we had guys that could set the ball up. All of a sudden, this guy came in and his hands were velvet and the balls would be up and we’re like, “Boom,” all day long. I was like, “This is crazy.” They recruited the person who is our best compliment, not the person we would have thought to go out and get. I like your insight around that. You’re not just looking to hire for that role, but who can leverage the team and then it’s the one plus one equals three, right?

Absolutely. There are a few other things that I look for. One of them is precise communication. What I’ve learned is that the precision of someone’s communication typically matches the precision of their thought process. In other words, if someone is a strong thinker that manifests itself in the way that they communicate. I do look for that in interviews. Another thing that I look for is a strong understanding of “the why” behind the results that they’ve achieved or in some cases, the mistakes that they’ve made. Our CEO likes to say, “It’s hard to achieve success. It’s even harder to know what drove your success.” If you can understand that deeply, you can be more likely to achieve great results in the future. If you don’t understand why you were successful, then that success is less likely in the future.

How do you take that mindset of what you’re looking for and that introspection that you’re looking for, and how do you codify that? How do you find it in the interview process? Do you have other specific questions or tests? How do you go about digging for that to see what level that candidate is operating on?

There’s a couple of ways. One is I look to see that answers are concise, that they directly answer the question, rather than another question and that they don’t draw on for a while. That’s probably a good sign of clear thinking and the ability to relate to someone else. Secondly, I’ll ask the candidate about a particular situation, a specific situation that they’ve been through. I’ll ask them to describe the situation then I’ll have a lot of follow-up questions about, how did you measure success? What caused the success that you had? Did any conflict come up over the course of that success and how did you work through it? That way, you can understand not just do they have those reflective abilities, but also how do they behave in a work environment. That can give you a better sense of how they would deal with your team as well.

There’s another exercise that I tend to do with candidates that I found helpful. About several years ago, there was an executive coach who came to advise our leadership team. I wish I could remember his name and exactly the framework that he presented. I essentially adapted what he shared with us into an interview framework that I’ve used. In this framework, there are four different activities that you could be doing at work. For each activity, you can be highly energized by it. In other words, you’re in a flow state when you’re doing that activity or it might require energy for you to do it. You have to force yourself to do it or you might be somewhere in the middle.

Ideally, we have teams of people where everyone is spending time on the activities that drive the most energy for them. Other people on the team are spending time on the things that for that particular person doesn’t energize. That way, everyone’s thriving, we’re having a great time and we’re getting a ton of stuff done. Notably, in this framework, energy is different from strength. You might be good at something that you have to force yourself to do. For example, I can’t say that building three statement financial models is my favorite thing to do.

However, I’ve been trained in it. I’m good at it. For some reason, our FPA team, our Financial Planning Analysis team went on vacation and they needed someone to build a model. I could step in and build that but it’s not my favorite thing to do. I might be low on energy. I ask people to self-identify based on the framework, where they get their energy from, what causes them to have lower energy and we have a great conversation about it. I’ll ask them, “Why and can you give me an example of this?” It helps me understand how I could best set them up for success in a work environment.

We spent some time on that at one of our COO Alliance events and we called it Unique Ability. Trying to scope out, we categorized everything that was on the COO’s plates. We categorized everything they would do over the course of three months and categorize them in one of four ways either I for incompetence, C for competent, E for excellent and U for unique ability. The difference between excellent and unique ability was you get energized by doing it. People get energized watching and you are in that state of flow. A lot of times, we have stuff on our plate that we’re good at but we don’t love doing. If you can build that team, how do you have those tough discussions? Maybe they’re easy discussions. How do you have the discussions with someone on your team who’s working in areas or have projects on their plate that they might be excellent at but aren’t unique ability and you want to pull them off their plate to give them to somebody else? How do you have that discussion?

I have used the same framework internally on my team. I would recommend that as well. In that way, the teammate can be aligned on the types of activities that give the most energy. We can structure their role in such a way that they’re maximally focused on those over the course of their day and their week. Sometimes, if someone’s not energized by something, that activity will get postponed. It might take longer than expected or maybe the deliverable was incomplete. At that point, it’s okay to have a conversation with the team member and say, “I noticed that it took a little while to do this. It took a little bit longer than we expected. I’m curious, do you get energy from this?” Often the team members are grateful that you asked because they might be thinking, “This is the last thing I want to do. I’m not sure if I can raise it with my manager.” In asking them, you give them the permission and then you go, “We’ve got a team of capable people. There’s probably someone else who could manage this and let’s see if we can find you a better home.”

It’s amazing when you give that project to somebody who does love it. How much more excited they are, how much better the result is and how much faster they do it. Years ago, I was working on a memo that I had to send out to our 3,000 employees at 1-800-GOT- JUNK? and I was agonizing over the wording and the flow. I can’t write to save my life. I’m way better thinking out loud. I had this thing drafted and I’ve been spending a couple of days, I may be into my fourth or fifth day on it. Finally, I was like, “I need to get Katherine,” this woman who worked for us in our learning development. She’s a copywriter. “I’ll get her to see if she can take a pass out of it.”

She was excited. She was like, “I get to write your memo for you.” I’m like, “Yeah.” She was vibrating. I’m like, “You can write all my memos. If you get off on this, this is great.” She took it and it was like angels singing. I was like, “Unbelievable.” The real challenge is building those unique ability teams. It gets easier as we’re a little bigger. How would you advise companies that are maybe in the 50 employee size, where they don’t have enough of those unique abilities? What would you give them and guidance to start building out that unique ability team or that flow team? What would you call it?

You could call it the A+ Team, where they’re optimally energized. When you’re in an earlier stage company, it’s important to critically assess every hire. To your point, you have limited headcount. Every hire is a big decision. At the same time, you can mitigate the risk of hiring the wrong person by hiring people who get energized by many things. I tend to find that some of the best early-stage team members are generalists. Often they’re called athletes. If you’re not the person who likes sports, I’m sure there’s some analogy in the music or art world or some other hobby that might resonate.

I grew up playing sports, so I think of it as an athlete. You generally have a certain amount of excitement about perhaps the purpose of the company and the general trajectory you’re on. The people that you’re around with. You’re excited to do most things and be persistent in executing on most things. There are people out there that I interview with this four-part framework. The four different activities you do at work where they say, “Being totally honest, I’m equally energized by all of those things,” and I believe them. There are some people who are rounded in that sense.

They’re the Jack of all trades, master of none, which is exactly what you need that early stage. Once you progress past that into the more medium-sized enterprise-level, you do need the functional experts, right?


I’ve been obsessed with core values inside of organizations for years. When you were three, your mom did that little card walking away from the game of Uno with you. I went to church with my dad when I was around the same age. My dad went into the confessional, I thought he was going to the bathroom. He came out and I said, “How’d it go?” He’s like, “It was good. I was talking to the priest.” I’m like, “That’s weird.” He’s like, “No, I was telling the priest all the bad things I’ve done.” I’m like, “That’s even stranger.” He said, “All he had to do is say some prayers and everything was good again.” I remember going, “Wow.”

When I do bad things, we have a different discussion. I wasn’t allowed to do bad things and say a couple of prayers and they were forgotten. You don’t do the bad things. If the core values are core values, you live them. At times we have to fire people who break them. How do you go about those tough conversations internally with people who are first off the high performers? How about the results are solid but they’re not the culture fit of the core values aren’t being lived. How do you enter into those conversations?

SIC 75 | Gainsight COO, Allison Pickens

Gainsight COO, Allison Pickens: Ask your staff to self-identify where they get their energy from and what causes them to have lower energy. It helps you understand how you could best set them up for success in a work environment.


First of all, I do think that integrity is a non-negotiable aspect of any role and it’s a critical criterion for assessing someone’s performance or eligibility as a candidate. In situations we’ve had, my past work environments where there’s been someone who had some integrity violation. In my opinion, that’s typically a cause for immediate departure. You have to have a hard line about honesty and other forms of integrity. For some people, it’s not black and white maybe you’re skeptical of what this person is saying. You don’t trust them. You’ve noticed some shady things, but you’re not sure what’s going on.

I often find that those behaviors will manifest themselves in poor results. For example, they may not have the credibility from the perspective of their team. They may not be able to inspire people. There might be some frictions and cross-functional work that prevents them from achieving the results they need to achieve. Somehow all of these things tend to work together. You might make that decision about whether they’re the right person after a period of time where you’ve noticed the outcomes of what it might be more difficult to diagnose those for integrity.

Do you find that you learn about that individual more when you do some skip-level meetings too and you hop over them and talk to some of their team?

Sometimes in skip-levels, depending on your relationship with folks, people might be a little bit hesitant to speak up because they don’t want to rat out their boss. They’re worried about retribution. You have to create a culture where candid feedback is encouraged. There’s a lot of different forums to share feedback. You have a relationship with skip-levels, to begin with. They feel they can trust you and where people know that integrity is the most important thing. They’re willing to speak up. They feel comfortable and confident speaking up in situations where they see core values being violated.

At the same time, it’s important as a leader to be able to perceive those subtle signs that a skip-level is unhappy with their manager. They may not come out and say directly, “I don’t think my manager is a good manager. You should fire them.” That’s probably unlikely. They might say things like, “A decision was made that I disagreed with.” They might use the passive voice and not use their manager’s name. There might be some other more nuanced signals that you could look for.

Tell us how you do a skip-level or what skip-level meetings you are doing. There’s a bit of an art to that and it’s rarely talked about.

This becomes increasingly difficult as you manage a bigger scope. I do regular one-on-ones with my direct reports. I’m no longer at a point where I can have regular skip-levels with their direct reports as well. I do try to make sure that I reach them in a few different ways. One is that I do twice monthly round tables with groups of about ten people across the company, which can include all levels essentially below my direct report. That allows me to create an open conversation. It’s helpful to the discussion. People at this point are candid in sharing with me. I ask them a few questions. One is, what is one concern that you have? What is one thing that pleasantly surprised you recently? What is one wish that you have for our team?

I noticed if you go around and you ask people to answer at least one of those questions or more if they like to and you say, “I want everyone to participate,” eventually, you will get out those things that need to be surfaced. You also have to process the conversation by saying, “I appreciate radical candor. There’s nothing you could say that would offend me. I’ve heard it all. This is an environment in which you can share everything and I will not be sharing who said what after this meeting. You don’t have to worry about any form of retribution.” There’s another thing I do to stay in touch with skip-levels, which is weekly as well as quarterly, I’m thinking about what are my top priorities. Typically, there are between three and five. I want to make sure that I’m in touch with people in the organization who are particularly involved or their roles relate to those priorities in some way. Depending on that priority, I might be connecting with some skip-level folks more than others.

I laughed because you said, “I don’t have time to do skip-levels with my team,” and then you gave me two of the best systems that I’ve heard in years of talking when working with COO’s, skip-level meetings that you’re doing twice-monthly, doing round tables with ten people. Honestly, most leaders probably do that once a year at best.

I would be nervous for those people.

I’m nervous for them because they’re completely out of touch. I’ve always subscribed to Tom Peters from In Search of Excellence when he had to talk about MBWA, Management By Walking Around and you can leverage that by doing it in groups. I used to take five people every Wednesday for lunch for an hour at this little restaurant around the corner. It was a half a block away. We’d all sit down at the same table every Wednesday at 1:00. We do lunch and then we go back to work. It was always a mix of people. My EA would set it up for me and I would ask questions and listen. How do you prevent yourself from engaging when somebody says something and you want to engage but you know that there either is another side of the story or it’s more of their VP’s call and you got to bite your tongue? How do you prevent yourself from getting sucked down that rabbit hole or going where you maybe shouldn’t go yet? Do you go there?

You don’t want to bypass your direct reports. Typically if someone expresses a concern in a roundtable that it should be under the purview of my direct reports act on, I might say something like, “Thank you so much for sharing that, I probably wasn’t aware of this. It’s good to know,” and I might say, “Have you raised that with your manager before?” They might say, “No.” I might say, “Would you like for me to have a conversation with your manager or would you like to have a conversation with your manager about it?” I might also say, “I wasn’t aware of the impact that this decision was having. I’m sure so and so had good reasons for making that decision, but I want to understand a little bit more about how they were thinking about it. Why don’t I follow up with you later once I have a conversation with them?”

You’re showing they’ve been heard and you understand it and you’re going to look into it all and thank you. That’s all they want to. Those are huge two systems. You could write a book on skip-level meetings, doing those two things from my perspective. Go back to core values again, inside of the Gainsight. How does your organization screen employees for core values? Everybody have core values, Enron had them on the wall but they never lived them. How do you guys live your core values day-to-day? How do you continue to push them and communicate them and through the organization?

It’s important that values are not merely posters on a wall, which we have as well as great decor but it’s by no means sufficient. There are a few ways in which we infuse values in day-to-day life. One is that we refer to them a lot. Our values have catchy names. They’re easy for people to remember and we bring them up in meetings where we’re making decisions.

What are they?

There are five. One of them is the Golden Rule, which we’re all familiar with, “Do unto others as you would have them do unto you.” There is, “Success for all,” which means, in any decision that we make, we want three different stakeholders at minimum to have a win from that decision. There are employees, customers and investors. We don’t want it to be a trade-off across these three groups. We want to create win-win situations. Our third value is childlike joy, which is a fun one. This is all about having pure fun and creating fun through our work even though it’s challenging. Our fourth one is Shoshin, which is a Japanese concept that means beginner’s mind. I love all of our values but this is one that I’ve contributed to Fairbit.

When I joined Gainsight, the first three values existed and the second we all created through a lot of dialogue. Beginner’s mind to me is important. It speaks to the idea that, if we ever consider ourselves to be pure experts on a topic, we’re probably missing something. It’s easy, especially if you develop a lot of specialization that you become complacent and that you overlooked something that you could be learning. You might develop certain blind spots. Those unknown unknowns can be disastrous for business. We always want to challenge ourselves to be learning and reflecting on our current situation and our future. The fifth value is, “Stay thirsty, my friends,” which means we want to win. Our purpose statement for our business is to prove that you can win in business while being human first. That’s our overarching purpose and the values are supportive of that. The notion is that even though we have values that are dear to us, we’re leveraging those values in pursuit of winning.

You guys have done a great job with your core values. I’ve always said you limit them to 4 or 5 core values. You can’t have 8 or 10. If you get more than five, it’s impossible to live them all. I love that you have short little phrases. It’s hard when a company has a single word. Integrity or passion, it’s like, “What does that mean?” I like that they’re phrases that are easy to remember. The only time I’ve ever seen a company where I’ve said, “That’s single word makes sense,” their fifth core value is simplify and I’m like, “That’s so good.” To make it a short phrase isn’t simple, simplify is perfect. I loved it. Your dad would like the Shoshin one, the beginner’s mind, would that appeal to your dad do you think?

They would appeal deeply to both my parents. They are big fans of education and learning.

You mentioned the cadence and the rhythms for strategy and execution. I want you to walk us through a little bit of what you do related to strategy and goal setting, especially because our next COO Alliance event, that’s our core theme for the whole two days. I’m intrigued.

SIC 75 | Gainsight COO, Allison Pickens

Gainsight COO, Allison Pickens: Write your corporate values with catchy names. Bring them up in meetings where you’re making decisions. It makes it easy for people to remember.


We used to OKR framework, that’s John Doerr and others have written a lot about. OKR stands for Objectives and Key Results. The idea is that the objective captures the spirit of what we’re trying to achieve and the KR is the metric that helps us understand whether we’re achieving the spirit of that objective. It’s important to have both because often we can achieve a metric but in a way that doesn’t help us achieve our long-term goals. Sometimes we might think that we’re achieving the spirit of a goal but we don’t achieve it enough and therefore we don’t meet the metric.

Having both as a pair is important. In general, as a company, we essentially have five high-level OKR’s across the business. Those OKR’s translate into three OKR’s each. Each one matches a specific initiative that we have at our company. That has a cross-functional steering committee responsible for it, as well as an executive sponsor who’s overall accountable and a team lead that organizes the steering committee. That way, we’re taking these goals and we’re translating them into an organizational structure or framework. That allows us to execute on that in a way that’s totally aligned across the company.

Before we had this OKR framework, we found that the functions across the company were sometimes heading in different directions. Particularly when you get to a meaningful scale that can be disastrous for your company to have two functions that are not aligned on what we’re supposed to be doing. The cascading of OKR’s has allowed us to make it clear on how two functions should work together. How they should weigh trade-off and how they should support each other’s goals. Particularly in situations where there’s a clear dependency of one team on another.

You mentioned getting a meaningful size. I was thinking about the size of your organization. You’re in that approaching or already there that enterprise-level company. With 650 employees, you’re in that enterprise-level zone. How do you orbit that giant hairball and avoid all the corporate bureaucracy and red tape and bullshit that tend to happen when companies get big? What do you guys do? I have a sense that you don’t have that kind of organization. I have a sense that you have a little bit of a professional, focused, growing and fun but without the bureaucracy, am I right?

I’d like to say we’re perfect, but we’re not. There are challenges like any organization has. I would say that one thing that’s been effective for us in keeping up that entrepreneurial culture is in making clear in what stage and initiative it’s in. Especially now that we’re a multi-product company, we’re launching new products. We try to make it clear if a certain initiative is in the Zero to One stage. It refers to the book that Peter Thiel wrote about essentially how do you build things from scratch and get them to that critical threshold of truly existing and being ready for the next stage of scaling.

There are certain products that we’ve launched, for example, our CDP product, our CX product, our RO product, which is a part of our customer cloud. These products were previously in Zero to One stage, which meant that we had to execute on a product roadmap. Our product marketing team had to define the positioning in the market, how we were going to message this content for training our sales and marketing teams and other teams. We had to create certain mechanisms for delivering these products.

Most importantly, in the early stages, get a few initial customers to buy these products so that we can prove that there’s truly revenue opportunity. There’s some product market and that we can start to match early set of visionary advocates who can propel the growth of those products into the next stage. When new initiatives are being launched at a bigger company, it’s easy to deprioritize them. It’s also easy if you pointed out for red tape to get in the way of that fledgling new plant. You got to make sure that there’s a focused initiative as a part of it that a small tiger team is involved not too many people. It’s carved out in the context of your broader OKR’s.

Do you take some of those same mindsets into your meeting rhythms as well and not having too many people and not having a long drag out meetings that go nowhere? What do you do internally? I wrote a book called Meetings Suck to try to teach people how to run meetings and how to attend them, how to even participate while they’re there. What things are you doing internally to make sure that your meetings run well and have a good meeting cadence in it?

We made a lot of progress with this and it’s taken a fair bit of changed management for us. Meetings tend to run well when there’s a clear agenda. Everyone is prepared. There’s content that everyone can look at and the presenters have anticipated all the questions that will come up in advance of the meeting and I’ve prepared answers for them. There are a few things that we’ve done. One is that for the meetings that we have in the context of our rhythm we call them rhythm meetings. They might be monthly business reviews, weekly business reviews, quarterly business reviews.

For those meetings, we have a certain template agenda. It started with the executive sponsor communicating the status of a particular OKR. If that OKR were off track, they would have to prepare in advance of the meeting. A pass to green, which is essentially a waterfall chart that allows you to see what are the components of bridging the gap between where we are to stay and where we need to meet. They would go through the different OKR then there would be a final section of the agenda where the rest of our executive team could each go around the horn and offer their feedback on what they heard. That was a good start and we’ve evolved that over time. One way in which we’ve evolved it is we require the deck for these meetings to be shared in advance so that there’s a pre-read for the meeting. That being said, sometimes it’s hard to make sure that everyone does the pre-read. If you’re requiring time for the pre-read and also time for the meeting, that adds a lot of working hours to people in place.

What we’re experimenting with is having the first ten minutes of every meeting be a pre-read designated time for people. They come to the meeting. There’s ten minutes of silence where people can read the deck and then we launch into the meeting after that. There’s another thing that we’ve done recently, which is we slim down the exact composition of attendees for each meeting. The steering committee for each initiative has been largely given that they cover many functions. We’ve often had multiple people within a given function at different levels within the meeting, which ends up diluting accountability at the top in terms of senior folks. It makes it less clear who’s accountable for certain action items following the meeting. We’ve tried to reduce the meeting size to what is minimally necessary.

I love that you’re doing the pre-read. Jeff Bezos and Amazon have been huge on that since the earliest days.

They’re a huge inspiration to us.

I talked to one of the prior interviews, a guy named Andrew Way, who I had on the show. I’m going to say he was Amazon employee number 120 and he left when they were 15,000. I might be off by 5% or 2%. He was in the first 200 or 250 and then left when there were 15,000, 20,000. He was saying that that meeting cadence was there when he started. He’s been doing it ever since with his company. He’s COO, this has been huge. As you identified, people either don’t have time or they don’t spend enough time or they gloss over it. If it’s that important to tell people to do it, make it a part of the meeting.

One of the things that made this rhythm process successful is I hired a Director of Business Operations who’s helped us build out that rhythm cadence even more with all the depths of the templates exactly who’s in each meeting, helped us refine the wording of our OKR’s and how they cascade. I would recommend that COO’s have that function. Note that business operations are separate from sales operations or maintenance operations. In this case, it’s more of a strategic planning and execution type of glue.

I’ve got a couple of final questions. One, I’d love to know about your skillset. You’re skilled. You know what you’re doing. You got all the experience and the theory behind you to back it up, which has been amazing, but we’re human. Every day we wake up and this is the biggest thing we’ve ever done. It’s like, “How am I going to do this one?” Where are you working on your skills? What are you focusing on growing and getting better at do you think?

I’m not perfect. I’m always trying to learn. Especially, in that spirit of Shoshin, where you constantly recognize that you’re a beginner. In particular, what we’re learning and what I’m learning is how to run a multi-product company. There is a lot of complexity to that. There are big questions such as should you build that new product or should you acquire? If you acquire a company, how exactly should you integrate it to leverage the resources of your current company? To fulfill the notion of synergy that you had that motivated the acquisition of being with while also giving enough space to that entrepreneurial initiative so that it can grow.

SIC 75 | Gainsight COO, Allison Pickens

Gainsight COO, Allison Pickens: To avoid meetings that go nowhere, designate the first ten minutes of every rhythm meeting for a pre-read of the presentation deck and reduce meeting size.


How do we position ourselves in an expansive set of categories that were operating and not that we have a multi-product environment? How do we enable folks across our company to understand and learn about the technical aspects of these new products as well as how to message them? How do you help construct roles where people might be focused on multiple products and need to do well in all of them? These are some of the big questions that we’re working through the company and that I’m in particular learning a lot of.

I love it when you can apply some of the learning to specific things. Often people are just reading the next business book or going to the next conference to learn in general. It’s random and you might stumble across something. If you can apply your learning to what you’re working on or what you’re thinking, you go and look for those resources to learn. It becomes a much stronger ROI. Final question, Allison Pickens. If you were giving the 21-year-old you or the 22-year-old you some business advice, what advice would you give yourself that you now know to be true?

In some ways, I was smarter when I was younger. I remember when I was eighteen years old, I had to fill out a form when I was graduating high school. That would then be returned to me ten years later. I remember when I received that ten-year-old letter from myself, there was a line at the end that says, “Always focus on what you’re passionate about.” To an eighteen-year-old, it’s clear that you’ve got to go where your energy is. I often think back to my eighteen-year-old self to remind myself to focus on what energizes me. Great teams and great performance are all about channeling energy.

Who sent you back the letter after ten years? The school?

High school. Yeah, it was a wonderful service.

That’s cool. It’s a great idea. Allison Pickens, the Chief Operating Officer from Gainsight, thank you very much for sharing with us on the show. I appreciate your time.

Thanks for having me.

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About Allison Pickins

SIC 75 | Gainsight COO, Allison PickensAs COO at Gainsight, Allison Pickens has been right-hand to the CEO in scaling the company from $1 million in revenue in early 2014 to 650 employees today. Along the way, Allison developed industry-recognized thought leadership on scaling a SaaS company.

Allison was named one of the top women in SaaS and top 50 people in the sales and business development industry. She is part of the Fortune Most Powerful Women community. She has spoken at dozens of conferences, written many dozens of blog posts, is the host of The Customer Success Podcast (50+ episodes), and has recorded dozens of other podcasts. She has served as an Independent Board Director for two companies and is an Executive-in-Residence at Bessemer Venture Partners. She has a passion for working with CEOs to help them grow their companies.

Allison started her career in management consulting for Fortune 500 companies while at BCG and later worked in private equity investing at Bain Capital. Allison has degrees from Yale University and Stanford University. On weekends you can find Allison geeking out about philosophical topics, learning about the gut biome, or hiking in the Marin Headlands.


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