Productboard COO Greg Strickland on how to balance growth and innovation, collecting mentors and personal development, managing through change, SMB to enterprise shift, and the competitive advantage of startups

00:06 - Michael Koenig (Host)
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01:01
Hello and welcome to Between Two COOs, where phenomenal chief operating officers come to share their knowledge, advice and, at the very end, a crazy story. I'm your host, michael Koenig, and our guest today is Greg Strickland, coo of Product Board, which is the leading product management system, helping product teams from companies like Microsoft, zendesk and Avast get the right products to market faster. I'm a former customer and I can attest to that, and it's no surprise that they're nearing 100 million in annual recurring revenue. Prior to Product Board, greg was the COO at Periscope Data and before that, the International General Manager and VP of Global Ops at Box. Greg, welcome, thanks for being here. 

01:40 - Greg Strickland (Guest)
Thanks for having me, Michael. I'm excited for this. 

01:42 - Michael Koenig (Host)
Fantastic. In a previous podcast that you gave, you mentioned that you're, and I'm just diving right in here. 

01:51 - Greg Strickland (Guest)
Let's do it, I love it. 

01:54 - Michael Koenig (Host)
You mentioned that your success has come from saying yes to new opportunities, especially those ones where you feel out of your depths and this is not only quite common for COOs, but it's my entire career as well has just been through saying yes. A question that I often get is how do you know what to say yes to? And I have that question for you what guides your decision making? 

02:23 - Greg Strickland (Guest)
Yeah, I think if you approach it as what the business needs in order to succeed or in order to continue to push forward and then is anybody else able to do it or willing to do it or have the amount of sort of passion and buy in for the business that can push themselves to go achieve it, I think usually the answer is yes Most times. 

02:44
There's certainly things that if you prioritize your career over this aspect of learning and progressing the business forward, then you tend to say no more often and I've just never had that mentality and this is why I love startups, because it's the amount that you can learn in a year is like three to five acts. If you just went and took a singular IC role inside of a large organization and I've spent in a 20 plus years doing that and through it there's a ton of work that has to get done and there's never enough people, there's never enough resources. And if it's a big, meaty, important project or initiative and you have some level of confidence in yourself and you like to figure things out on the fly and push, then it's always a great option to say yes, I think, yeah, I think it's against like personal career versus like business outcomes and I always optimize for business outcomes. 

03:33 - Michael Koenig (Host)
That's interesting. So it's experience over title. Get the experience, the title will come eventually. 

03:40 - Greg Strickland (Guest)
That's how I've always believed. That's what I've always believed and I know there's a path to COO and I don't know if there's any sort of magical path, but for me it's always just been fundamentally saying yes so that I could develop a broad brush of experience across multiple disciplines and departments, understand what it takes to run certain aspects of the business. And you get that by saying yes to cross functional projects. You get that to say yes by standing up new departments, going from zero to one, interviewing a bunch of people, hiring really great people, learning from them and putting your ego in check and making sure that they're successful. And I've done that my entire career and I just love that aspect of learning and trying new things, like this podcast, for example, is out on my comfort zone, as I mentioned. 

04:21 - Michael Koenig (Host)
But I said yes, so here we are. Yeah, I appreciate it. Thanks for saying yes. Have you ever said no? 

04:28 - Greg Strickland (Guest)
I'm sure I have, but I tend not to remember those ones because they're few and far between, and for me to say no, it's usually probably one or two camps. One. I actually think there's somebody better to do it and so I'll recommend someone. And if it's an up and comer and I've just seen them operate and I have a lot of faith in them and I want them to stretch and push I'll actually default and say let's give this person a chance to spearhead and drive this initiative. 

04:51
And that certainly happens more and more as you get later in your career. You try to, whatever it is, pay it forward or get other folks to experience that career journey. And then there's other ones, like certainly when startup land, first time founders, the ability to make quality decisions based on experience is all over the map, and so sometimes I say no because I don't think it's the right business decision. And that's less around, like taking an opportunity that we think is all aligned is going to drive business outcomes. It's more around. I just fundamentally disagree with the strategy and that's pushing back and having that dialogue before. We just need your can do what the CEO wants to do. 

05:28 - Michael Koenig (Host)
We have a similar background in that we both spend time in early stage companies. One of the challenges that you get that's great, as you mentioned is the ability to just dive into all sorts of different things that you otherwise wouldn't necessarily get the opportunity to do. A pitfall, though, especially as you're early in your career and I know I experienced this at certain points is that in going to those early stage companies, I didn't necessarily have someone I could learn from in doing that thing. It was trial by fire, right, and I learned from doing it the hard way. Did you have that similar experience? Because that's also when you're early in your career learning from someone is so valuable. 

06:14 - Greg Strickland (Guest)
It really is, and I think this is for sure one of the challenges not having a mentor or an expert in the company that can help you guide yourself through it, find the pitfalls, not walk over the cliff, but sometimes you need to walk over the cliff. 

06:27
So I'd say there's learnings in that as well, as long as the sort of whole analogy of one-way doors and two-way doors. There's a lot of two-way doors and organizations. There's like 90%. So you make a mistake, you walk back, and so making sure it's not a company ending project that you're going to fumble, I think is important. But I'd also say like over the last I think 10 years, it feels like the access to mentors, the willingness for people to jump in quick-link ping. They're willing to share some of their expertise. There's so much content being produced out there right now blogs from season VCs and operators that allow you to do a level of homework and really understand, because there's this academic aspect of it, not just blindly charging up the hill and I think if you balance that and you can get a solid mentor or a group that you can bounce ideas off of, you can alleviate some of those chances of going over the cliff, blamely. 

07:17 - Michael Koenig (Host)
That's so funny that you said that I've been reading Matt Blumberg's blog for 20 years and there's so much good content there and I'll link to this in the show notes. Matt Blumberg, CEO and founder of Return Path, which was a Union Square Ventures company. Fred Wilson has called him one of the best CEOs out there and he's written prolifically a ton of books. There's my bookshelf startup, CXO, which is one of his. But nonetheless, like you said, I've read this guy's blog for so long and then, after 20 years this is a couple of months ago I actually just reached out to him and I said like I longed you know, long time listener, first time caller type of thing and so generous with his time and, like you said, there are people who are really willing to give you that opportunity, to give you that time to ask some questions. But you mentioned that now more than ever, or rather over the last 10 years, that's picked up speed. Why do you think? Just out of curiosity, and we can hypothesize here. 

08:25 - Greg Strickland (Guest)
I don't have a sort of grand hypothesis on it. I just I think startups have gone through amazing ebbs and flows over the last decade and a half. Certainly, when I came out of college was calm bustin, we lived through the 2008 macro recession and went through my own experiences with layoffs and risks and downsizing and IPOs and acquisitions, and so even myself doing this podcast is a bit of content that I'm now sharing, a journey, and I think there's more folks that cut their teeth over the last 10, 15 years that are now sharing their learnings, and it's wonderful. I think it's great. I also say that there's there's always luminaries and there's always books that exist. 

09:03
The hard thing about hard things with Horowitz and even Frank Slutman's amp it up like just the operating style and radical candor. There's just, I think, a greater willingness to adopt and have this aspect of perpetual learning and the learning culture that I think is very present in startups and has been over the last 10 years, and so I think that feeds the content engine and feeds the mentor engine and overall I think it's great. There's nothing better than working with a former operator and having them share their kind of war stories and hearing that you're not alone. You're not going through it for the first time. 

09:37 - Michael Koenig (Host)
Let's talk about the first time. You mentioned working with first time founders. That is a challenge. It's painful, it's incredibly rewarding because you get to meet some of those luminaries that you talked about, some real incredible people with genius, but you've kept doing it. 

09:58 - Greg Strickland (Guest)
Yeah, glutton for punishment for sure what's going on there. 

10:02
Yeah, the honest answer is I've always been entrepreneurial. I always wanted to start my own company. I'm just not that creative. I've had maybe three great ideas that I thought of that have eventually turned into. Someone else had the idea. They turned into great businesses and that's awesome, but I just never had that idea that kept me awake at nine, said I can't stop thinking about this. 

10:23
So my way of living that dream is by partnering with people who have a great vision, who are on a path to realize their vision, and I want to help them. And it is painful. It's physically, emotionally, mentally painful, and I really think there's a spectrum here. If you really buy in and you're all, in which I am, I tend to be either all in or all out. I'm pretty binary in that way. 

10:45
And if I'm all in, then I care a lot about the business. I take a lot on my shoulders. I want to shoulder the burden and do as much as I possibly can, because I know how hard that job is. I know how hard the CEO job is and how lonely it is, and the more I do that, then that inherently gives you more responsibility because people can feel that you actually care. And yeah, I just I love that aspect of buying all the way into something and going as hard as you can to try to help somebody realize their vision, but then also bring everybody else in the company along for the right, because I think it creates amazing opportunities. 

11:18 - Michael Koenig (Host)
And even with first time founders, there's always something to learn right, absolutely. 

11:23 - Greg Strickland (Guest)
Oh my god. Every founder that I've worked with I've learned something. I've worked with incredibly product-oriented engineering background founders who think and solve a problem in a very different way than I would. I've worked with very operational, data intensive founders. I've worked with ones that are just there's the Aaron Levy of the world, this sort of Nick Metta cohort that came out of that incredibly expressive, very creative, very inspiring and, almost accidentally, in how they operate. And so everyone, every person, is obviously different. They have their strengths and weaknesses, but you can constantly learn and develop from working with these folks. 

11:58 - Michael Koenig (Host)
You've worked with quite a variety that you just identified. Which have you found you most gravitate to? Which type of founder do you love working with from, say, a complementary perspective? 

12:11 - Greg Strickland (Guest)
Yeah, I've never owned product or engineering. You know I have worked with them extensively when trying to accomplish goals, but I tend to enjoy working with product and technical founders. I think my strength is in helping scale up the other aspects of the business finding go-to-market leaders as well as like finance and people, ops and figuring out how to operationalize the cadence of the business, and those are things that usually are not core competencies of those types of founders and something that they appreciate and fits into a natural slot. That said, I've worked. When I was doing some level of consulting for about two and a half years I worked with second time so who tended to be more go-to-market oriented, but there's still a lot at which you can augment and support them on. But, yeah, if I were to have to choose, I love the product, I love the engineering focused founders. 

12:58 - Michael Koenig (Host)
Who obsess over what they're building right. Just absolute obsession, which you have to have in a founder in order to be successful. Let me ask you it's interesting we'll see companies launch that essentially do the exact same thing, the launch at the same time. One of them will fail, one of them doesn't. How does? 

13:18 - Greg Strickland (Guest)
that happen. 

13:19 - Michael Koenig (Host)
What are the conditions between the failure and the success? And I ask this because you've been on the success side- yeah, you were in the valley long enough. 

13:31 - Greg Strickland (Guest)
You've seen the failure side too. But that's also obviously learnings. 

13:34 - Michael Koenig (Host)
Yeah. 

13:35 - Greg Strickland (Guest)
I don't know that. There's no silver bullet with anything right. It's the combination of a bunch of lead bullets and I don't think you can discount the amount of passion and vision that is required from a founder. Do they have? Not only do they build something because they thought it was interesting and cool, but they can actually see where it's headed and they bring people along for the journey. And then, if that is well defined and constantly reiterated with the team, then the decisions behind that wake, if you will, are much easier and you start to stack them up, if you want to like, with Product Board as an example. 

14:07
I think the vision really is to be almost the sales force for engineering product design. It starts with workflow management and then, through workflow management, you start to capture a ton of data and that data becomes valuable in and of itself, just like when you run Salesforce reports. And if you have that strong vision and the decisions that you need to make and where you're headed as a business start to slot behind it and you get greater execution. I think if you don't have the vision and you just start with a product that's feature functionality and solving a basic problem and you're not heading and driving the team in the direction. 

14:41
From the perspective of sort of 12 to 24 months, it's really easy to get sidetracked, it's really easy to lose focus, it's easy to chase the shiny object and when you're in a startup, you have only so many resources and you really need them all pulling in the same direction. So, yeah, I'll give shout out to Sluteman's Amped Up book. It's really focus and execution is the big piece that is mapped behind a really strong vision, and I think that is the difference. But also, if you've ever played poker, some element is luck. Let's not ignore that. 

15:14 - Michael Koenig (Host)
There's always luck. That, what is it on how I built this Skyrouse, will ask. At the end, you know how much of it was skill, how much of it was luck, right? Anyone who says it's all skill, come on. 

15:25 - Greg Strickland (Guest)
Yeah, I mean, you know, like Box, I think, was a good example. Aaron was maniacal, had a vision, constantly pushing, selling the dream, and we would scaffold up a ton of resources behind that to go execute on it. But the iPad dropped in the middle of that journey and he ran through the organization screaming we're going to be the first business app on the iPad. And so you have these like market dynamics that sometimes shift in your favor or sometimes against you, and how you react is incredibly important, and I think some of that has to come from the founders and CEOs, but also the nimbleness of the organization in order to ingest it and actually make it real. 

16:00 - Michael Koenig (Host)
Let's talk about that part of ingesting change, especially with startups, and I know a lot of startups right now are having a holy crap moment with generative AI and it's forcing a lot of people to look at their business model and go, okay, how do we have to pivot in order to stay alive? At this point, what's your approach to managing through that change and keeping your team focused and motivated? 

16:29 - Greg Strickland (Guest)
Yeah, I think there's two sides right. There's the product side and then there's operational side. I think the operational side it's incredibly exciting being able to leverage what the sort of promise of AI across all of the organizations on how we can operate more efficiently and effectively. On the product side, I do think AI is a product problem. Now. It's not like an engineering problem, because it's a product that has to figure out how and where to insert AI into the existing flow or how to reimagine existing feature functionality by putting either AI at the front or on the side. And so, for a company like Product Board, we I think we ran a survey where everybody is effectively 70 or 80% are trying to figure out their AI strategy in their own product, and it's going at the speed of light which you'd expect and it's overall, I think, really exciting. 

17:15
We've gone through monumental shifts as well. This one feels like another one and the people who can adapt and see the new use cases and reimagine their own product and the functionality. In a world where manual processes go away, data insights are automatically generated. You don't have to have spend three hours crafting content anymore. That just, I think, frees people up to go and be creative and in order to adapt. Again, that's the nimbleness of the organization. The competitive advantage of a startup is that you can move fast. You have less people, you can reorient OKRs and goals in a month's time, in a week's time maybe, and you can deprioritize things and reprioritize things. That type of work takes weeks, months, years in large organizations, and so it's that speed. I think that is the competitive advantage for startups. 

18:05 - Michael Koenig (Host)
As a leader? How do you, let's say, buffer your team from some of the whiplash that can come with that? 

18:11 - Greg Strickland (Guest)
One is just that expectation up front. I think you can't ignore it and you have to say it and you have to source for it in your interview process. Like this is a dynamic place. Everyone says dynamic, fast moving, like that's what everybody talks about, but the reality is you need to give some level stability to actually get things out the door and learn from them and then others. You have to realize that your reporting cadence and your goal setting cadence it needs to be faster, and so goals will change, resources will move, and so one is just like building a culture around that and making sure people understand it and then protecting initiatives that are longer term, that you fundamentally believe need to be true, and you kind of rank, fence them, you protect those teams, you give them a charter. 

18:51
That's a little bit longer. And then other parts. You just know that you're on sprints. You're on a. We're going to take you off this one sprint with this one experiment and we're going to go in this other direction and we're going to see which one actually materializes better results. So there's no. I think the easy answer is there's long term initiatives that are going to be true because they're attached to your vision and you need to invest because they take a long time to materialize. And then there's everything else, that is, you're trying and experimenting and figuring out and launching new campaigns and you're doing new product releases, and so you should be able to insert into that nimbleness of most of the organization. 

19:28 - Michael Koenig (Host)
In there. You mentioned how the operations have changed. Right, the need to generate content and you have a go-to-market focus. You are a largely commercial focused COO. At this point in your career, how has generative AI and just large language models gone about and impacted? How are you all applying it? To be more nimble and I Can't think of the word right now, but you get what I'm saying leverage the power. 

19:58 - Greg Strickland (Guest)
Yeah, right the light, yeah, yeah. 

20:00
Yeah. So my career has gone through multiple iterations. So I've been like the more CFO, operational, hr kind of finance COO. I've also been like the interim kind of take over all the go-to-market and align the teams. So I've seen a wide spectrum of it. 

20:14
I would say for us we're constantly experimenting with, with generative AI. There's a couple very obvious use cases. There's the content piece, there's product marketing, there's summaries and no building and design elements that you can get really creative with. We're using it in sales outreach. You can do an amazing amount of research on a prospect to start to build bespoke Outreach sequences and I think there's a healthy amount of experimentation for our own product. There's a lot of applications that we can do. 

20:44
We effectively have these kind of three modules. You have the insights platform, prioritization and road mapping. If you think about the insights bucket, we're doing integrations with all these companies. We're pulling in all this customer research. Like it's a very obvious place for us to apply AI to where Product managers go to research and if we can automatically Highlight some themes by segment the biggest customer, smallest customers, customers in certain regions, customers in certain industries Like that's incredibly valuable and time-saving for product teams. So I think from our product perspective, there's a lot going on and we can probably apply it on multiple places, and then in our go-to-market machine, it's certainly around outreach, content creation, product marketing, summaries and even design. Everything is being experimented with right now. 

21:28 - Michael Koenig (Host)
Now the product piece is really interesting because you have proprietary data. But that data is proprietary right. It is customer data. You can't very well go and drop it into chat, gpt. How are you all thinking about that in terms of leveraging, being able to leverage that data? 

21:45 - Greg Strickland (Guest)
And. 

21:45 - Michael Koenig (Host)
I know we're getting way down the pipe in product, but just something I'm keenly interested in. 

21:51 - Greg Strickland (Guest)
Yeah, this is I mean, this is gonna be a great topic for a long time of how do you get people to opt in to beta programs around AI that are using outsourced language models and something that we're all Grappling with with, like everybody else and so I think there is one. You can't do anything unless your customers know what you're doing and they proactively buy into it and Absorb the risk and I think that's gonna be the reality for quite some time is that companies absorb the risk Because they want to try this beta field filter, or you can apply it to things that are not effectively touching customer data as a first crack. I don't know that there's an easy answer right now unless you're developing your own language models that are closed. So I think we're we're figuring it out and navigating it like everybody else, but I certainly the biggest piece is is communication with customers, acknowledgement of it, just like you would in your normal sort of T's and C's, but making sure that it's understood and the risks applied to it. 

22:47 - Michael Koenig (Host)
We'll be right back, okay. Does this sound familiar? Wake up, take a look at your calendar and see it's filled with meetings project meetings, stand-ups, weekly check-ins, one-on-ones, town halls and those are just the internal ones. Some are productive, but some are total waste of time and treasure. Be honest with yourself how many times have you thought this meeting could have totally been an email? I bet a bunch. Now consider that in the US there are 55 million meetings happening each day and 85 to 90 percent have no agenda. 

23:20
Fellow is on a mission to solve the meeting problem by offering the only meeting management tool that covers every part of your meeting workflow. By offering 500 meeting templates, integrated action items, collaborative meeting notes and AI recording and transcription, fellow helps teams and organizations get more done with less. Between two COO's listeners yes, you get five free AI meeting recordings. Go to fellow co to start your free trial and start having better meetings today. So I'm interested because, as I mentioned, I've used product board before, really loved it. My current company doesn't use it at the moment. How do you see ops folks being able to use product board? And I'm not trying to like give you all a promo. This is a product management tool, right that management piece having better operational efficiency. How do you think that operational folks, whether they're GTM or whether they're GNA focused, can use it? 

24:22 - Greg Strickland (Guest)
Yeah, I think maybe two veins I'll talk about, just so, the evolution of like ops people in general that are oriented around, go to market. So. So you think about CRM solutions and the creation of real-source sales ops. You think about like Marketto and HubSpot and Eloquah and the sort of the orientation or marketing ops, and I've got gain site and vitally and all these other companies that are coming around for CS ops. The same will be true with product and product operations. So there is there's a growing movement around product ops, companies that are orientated individuals that manage the system of record but are also driving the insights Through it and are effectively like running the process of product management. And we've seen that. And then we've seen it in large organizations and small organizations that make that investment. So I think there's that piece of the ops that is following the natural curve of some of these other organizations and then how other Operational teams can leverage it. If you do product Well, it's a very inclusive and collaborative process. You're gathering information from a bunch of different stakeholders and you're organizing it in such a way that allows you to prioritize the right things for the right business outcome, and so that's one piece of which there's a lot of collaboration between sales and sass and marketing. 

25:39
The second piece is every CFO right now Is trying to figure out the effectiveness of their engineering work. Right, like we hired a bunch of engineers, we have a bunch of product. People like what is the value, what is the ROI of this team? And it's never been as indexed as the go-to-market team. Sales people have a quota and you have a quota ratio of four to five X. Ote Marketing has ROI calculators and all their pipelines. Yes, has portfolio management of the book of business and the NRR associated with it. Engineering roughly and product roughly haven't had that level of scrutiny and I think that's changing, and I think it's changing in a good way, because you want to understand your inputs and outputs, your throughput and the effectiveness of it, and, and so I think this is another tie-in where your, your finance and your ops team Will eventually start to play a bigger role in how effective is your product org setting aside product board. 

26:30 - Michael Koenig (Host)
That can be a scary specter For folks and it reminds me of when sales force first came around and sales folks looked at this as big brother monitoring. Lo and behold, it becomes an indispensable product, or rather tool for sales. There are companies like linear DB which help engineers measure Estimation accuracy and code that's pushed, etc, etc. But there's a lot of friction to that adoption. So I'm just curious how do you see that playing out? And this may be out of your wheelhouse saying like well, that's a stupid question. 

27:11 - Greg Strickland (Guest)
Yeah, I mean I can. I can Conceptualize things pretty easily, so I have ideas. Certainly still needs to be developed like an individual a is not gonna adopt sales force. Maybe there's value on organizing all their opportunities, but they could probably do it and excel or do something else they feel like they would be effective. It's an organizational push because it leads to predictability, it leads to accountability and it leads to organizations making better decisions. 

27:38
Yeah, if you don't know what your pipeline coverage is and you don't know what your forecast is and you don't know where you're gonna end up, how do you make decisions on where to invest and not? And if you don't know the effectiveness of your engineering product design team, like, how do you know you can actually hit milestones? How do you know you can respond to customer needs? Are you building the right things that are associated with the company objectives or not? And you're gonna have leaky funnels in engineering my product and design, just like you have in sales and marketing. And I think it's less about fear mongering and control. It's more about, like, how do we plug those? How do we get better as an organization and can and consistently iterate so that we can improve our performance across the business, and I think that's what sales force has done. 

28:18
I think, in a lot of ways, this were gain sites and hub spots, and Marquettos have done that. They've given visibility to a flow that has been a little bit back room or cobbled together, and giving visibility allows you to have data and data allows you to make good decisions. So that's how I view it. I think that's the evolution I'll go through. 

28:34 - Michael Koenig (Host)
It's hard to argue with data. 

28:37 - Greg Strickland (Guest)
Yeah, you can, but it's hard. 

28:41 - Michael Koenig (Host)
Let's talk about prioritization, which you've touched on a number of times. You as a COO, you as an executive at product board, how do you go about prioritization? What is your approach and how do you guide your team the right way Way, without being too overbearing? 

29:03 - Greg Strickland (Guest)
Yeah, again, I think you have to have a vision. So you have a vision for the product, which is great, but you also have to have a vision for the business. You can simplify it in we started as an SMV commercial business and we want to be an enterprise company. What has to be true in order for that to materialize? And that will span across on every segment? Where's your enterprise readiness roadmap on your product? What does it mean for your DNA, your sales team, your marketing programs, the messaging positioning, et cetera? And so you can create a vision that we want to head in that direction. You can set goaling around makeshift of your ARR, and then you actually have to put the pieces on the board of who's going to do what and how do we evolve over time. 

29:42
So I think, if you pick that point and that's just one example some companies that are like expanded to different geos or launch new product lines there's a thing, there's always a thing that the company is headed towards and you can orient your teams around it. And then there's millions of different opportunities to celebrate small wins and accomplishments along the way. And so I think it's the direction and the vision. And then there's the level of checking in without being overbearing, and targets make it really easy for people to feel like they're on track or off, and me personally, I tend not to be overbearing. I like to hire really solid people who are self starters and they're constantly looking, maybe, for calibration or feedback, but not direction, because they understand where we're headed and they're pushing in that direction. And yeah, I'm just not never have been micromanager. I like to hire people that are that go after it Now. 

30:34 - Michael Koenig (Host)
what's your approach to giving that feedback and helping that calibration again, without seeming like you're telling them what to do? It's an art and I'm this is something I'm keenly interested in. 

30:47 - Greg Strickland (Guest)
I really do think it's about asking questions, giving people enough direction, and then calibration is asking questions. Have they thought of this? What about this option? How are you thinking about this eventuality? How will you know if this is successful? What are you judging your success on? Because there's there tends to be, a lot of outputs call it assets or events but what's the actual outcomes that you're driving to? Where the numbers that you want to see? Over what period of time? And the more that you do that with individuals, the less you have to do it, because they internalize it and then, when they come up with the, with an experiment, has numbers now, has numbers based on baselines, has numbers based on past performance. And now you're just you're being a sounding board on the tactics and the ways to approach it. 

31:34 - Michael Koenig (Host)
Let's talk about the revenue attainment. As I mentioned, you're nearing on 100 million. I hope that is not private. Is that private? I'll have to remove this. 

31:42 - Greg Strickland (Guest)
I have no idea if that's private, it's a little generous, but we're we're on that path and so maybe we can. We'll take that one as regardless. 

31:50 - Michael Koenig (Host)
Your revenue is growing. However, you've moved into enterprise and the enterprise market has gotten tough. Historically long sales cycles have become even longer. I know personally. I'm scrutinizing every ask, as is my CFO, or we call them a CF. No, which is what a good CFO should be. How have you all experienced that? You've gone through this before? You mentioned 2008, right, and how did you recalibrate to get ready for this and continue to excel? 

32:25 - Greg Strickland (Guest)
Enterprise is always tough Moving up market. As a startup, you have a lot of startup DNA and nimbleness that is valuable at certain stages, but then you have to appear like you're stable. So it's an absolute journey One, to just get the organization ready and two, to actually empathize with it. And three, it's just this constant iterative feedback loop of hey, our biggest customers are stress testing our product. We have to scale it. A performance or permissioning, everything has to evolve. So I think there's this like organizational readiness piece, and then there's the where does your product actually add value to these companies? And there's always a sliver that tends to adopt first. 

33:08
So for us, we found very clearly that we started in a startup selling the other startups and then we started to sell the bigger software companies, which is great. But there's a sliver there of companies that building software is not their core competency. You think about retail, you think about healthcare, logistics, financial services, like they're in the business of that. They're not in the business of building software, but they all have to build software. Now, retailers have to build ecommerce sites and digital loyalty programs and mobile applications. Healthcare has to build digital patient experiences when scheduling applications all these things, some of which were accelerated through COVID and some of which have just been long term trends, and so we, as a as an expert in the space, have a lot more to offer than just a system. 

33:52
We have the best practices, we have the learnings from some of the best software businesses on how they do product that we can share with these companies. 

33:59
So the change management value is huge. And then working, obviously with external partners. So for us, companies that we put in this bucket of digital transformation or product as a software, being their sort of secondary or even their third business model, like those for us, we find a lot of adoption and a lot of success. And so it's funny, like when things get hard, you find the ones that are working, you find the silver pieces and you go hard at it and you try to operationalize everything else and if you get really good at it, when the rest of the business comes back, you're back into kind of hyper growth mode. And I think that's what a lot of startups are trying to figure out what's the silver lining, what is working, what's not, how do I get more efficient on the things that are not working and how do I double down on the signal that is still there and that's going to be true for the next four to six quarters at least, right. 

34:43 - Michael Koenig (Host)
So, from an operational perspective, particularly when it comes to sales operations and, I think, on the commercial side, what's the advice that you tend to give to those companies that want to jump from the SMB to the enterprise space? 

34:59 - Greg Strickland (Guest)
Yeah, we, what we did at product board and this we've been on this journey for three plus years we made ourselves give ourselves a sort of scorecard, enterprise writing a scorecard, and I decentralized it and we had every department evaluate it. We've all worked in different sized companies. You know how your business operates and your department operates. Give yourself a ranking like what are the categories and then what's your score, and then we've leveraged that scorecard over the last two plus years to progressively make improvements upon it. 

35:27
And it wasn't a tops down initiative of like I think engineering, you need to do X, y and Z was engineers and products saying I think we need to do this level of rearchitecture to increase our scalability. 

35:39
And so you had a level of ownership at the department level, on the individual level, which I think was incredibly important. And you know, startups are filled with people, with experience as well, and you've got companies they've worked with, ones that have sold to enterprise and some of them not, and I think you can leverage that experience to the crowdsource. And then you, as a management team, make sure that you're focusing on the right pieces in the right order and I guarantee you like moving up market as a total team sport. It's 100% a company level initiative and there's other companies that just never made that transition or have always fought against it because of the core DNA and because of the founders, and so you really have to understand, as their willingness and a belief, that this is where you're headed, and because if you don't have that, then you're just pushing a boulder uphill. 

36:22 - Michael Koenig (Host)
One of the things that we've talked about here several times now is feedback feedback from your customers to the rest of the organization, whether that be product, whether that be engineering. What have you? How have you gone about establishing that? What are some best practices that you've had? 

36:43 - Greg Strickland (Guest)
Yeah, we one product board is just designed with a module around feedback, right, it's capturing the support tickets, your sales opportunity notes, internal notes that exist, the Gong recordings, etc. And so it is this repository of just collecting it and making sure that you're thematically categorizing it which again, this is an application, for a for sure and then sharing those learnings and they actually get prioritized. But then you also have to speak to customers, right, you have to have those hinge points in an organization. Every company has these natural friction. They're all joints, right. 

37:15
Sales and marketing is a friction point, and sales and CS is a friction point, and CS and products is a friction point. 

37:20
I think there's good friction and bad friction. 

37:22
The good friction is actually pushing each other to have empathy for each other's roles and to understand the viewpoint, and so that is always something that we are constantly trying to improve upon in in a product or outside of the product, just by process, and it just it requires intentionality. 

37:38
Having your CS team and you know that you're moving up market, you orient what we call the pod zero model, which is like CS and sales and product and services oriented around our biggest customers. Knowing that model will help us clean the greatest insights and allow us to make faster improvements on our enterprise readiness, that we've been tracking our scorecard and I think that buy in like being involved in those process, hearing directly from customers where the struggling, where they're succeeding. Feedback on new features and functionalities is just so critical. And then the same thing with sales multiple whether you love or hate Slack, it's valuable multiple channels around upmarket deal feedback and you're capturing where what feature functionality we need, what we're missing, what's blocking deals or what is really help deals get done, and you just have to have that flywheel running at all times. 

38:29 - Michael Koenig (Host)
Yeah, backup pod zero model. Tell us about this. What is this? 

38:35 - Greg Strickland (Guest)
Yeah, I just kind of made up the name, but it was. You know, if you're a company that has traditionally served SMBs or mid market and now you're closed, your first 12345 enterprise companies, they're very different. They require a different delivery model or different timescale with a different statement of work. And if you just do what you've normally done with those organizations, just not going to work and you're going to get surprised at renewals. So we just, more intentionally, added a sort of dedicated services person, a strat, csm, product sort of sponsor and the AE onto an accounts, just a pod model where they're all collectively working to make sure that customer successful on the platform and then eventually expands and grows and becomes a champion. And for us, if you're moving upmarket, nothing's better than actually having customer champions that you can use in your marketing flywheel. But also who will, you know, tap their network and give you a good shout out, and so making them wildly successful, knowing that you're still a startup and immature, requires a level of investment. So we call that pod zero. 

39:37 - Michael Koenig (Host)
I love that. Let's talk about the feedback that comes in through that mechanism and again, I'm giving you some layups here. Everyone I swear product board has not paid me here. It's a really good product and we've got an experienced guy here to tell us about it. So let's talk about the let's call them feature requests. There's always a juggle between so and so enterprise. This can be, you know, 3 million ARR. We got to do it but they want X, y and Z. How do you go about doing that? Because now you've got A's pushing for something. Frustration can build, you've got engineering and product, which, yeah, it's nimble, but can you drop everything and add something new and monstrous? How do you manage that? 

40:23 - Greg Strickland (Guest)
You know, for me it's consistency of signal. Right, If you're whipsawing back and forth and building things that are completely orthogonal to your vision or what you want your platform to be, you get in trouble. And that's the companies that sell a really big enterprise a $7 million deal it's 90% of their ARR and then that company turns off and the company no longer exists. The startup dies Like. We've all heard those stories. I know those stories and that gets you into trouble. And that's by building very specific things for one specific customer that don't apply to a broader industry or use case, and so for us, you have to apply that lens and again, that's where you get the consistency of signal. 

41:04
Enterprise customers are asking for basic things like granular level permissioning and scalability of performance and exact level reporting. And we hear that oh, we know more that you hear it in your conversations than at bats the more you realize that this is this. Is it and yes, like if you're going to go industry specific or there's some industry specific product enhancements you need, or is it really just like a repackaging of your existing functionality? So there's a strategy level and a filter that has to be applied. You can't knee jerk and build everything that every enterprise person wants. 

41:34
You have to find the ones, that sort of the Venn diagram, the overlap and focus there, because the reality that probably solves 80% of your problems. And different products, different industries I'm sure that's a bit more nuanced. But for us, listening to the signal from our existing customers that we close, knowing that we said yes to an account, that we know that we're going to have to do some stuff right, we know that they're going to stretch us as an organization and that's good because you want to go through the learning. If you close an account like that without the acknowledgement that you're going to have to put a lot of work into it, you're in for a world world of hurt and so you got to have collective organizational buy in. You have to have this enterprise readiness concept and you have to listen and the more that you hear the same things it helps you really prioritize the stuff that sits in the middle of the Venn diagram. 

42:15 - Michael Koenig (Host)
COO. A lot of the time we're referees and also coaches. When you have that a coming in, I've got this great thing, but they need Bitcoin integration. How do you manage that? Because they're not going to get it. 

42:32 - Greg Strickland (Guest)
I'm a true believer in ICP. Work Like your ideal customer profile is so critical and it evolves over time. We took a more complicated approach. We took it from some best practices of the companies. We effectively built a dartboard. And the dartboard is like the bull's eyes. Where we've come from. 

42:49
We know we're really good at selling to these companies. We know what they want and we have it to offer. And, yeah, they'll always ask for new integrations and stuff, but it fits. And then there's the outer ring where we know it's a stretch like we know what they want. We may not know holistically, but we're willing to close them and work with them and co create the product, if you will, with them in order to get more companies that look like them. 

43:12
And you have like the outer ring where it's like we're just not going to sell them. You know like we sell to them and they're going to be unhappy and they're going to turn out like why would you put yourself in that business? And I think that level of focus is important for the organization to know. And those are the types of companies that really get it right on focusing on their ideal customer profile and then expanding that as they mature as a business. So, yeah, it's easy to say no to something that's just not. This is not good business. This is great, we'll get a sale and it'll leave us in six months. 

43:40 - Michael Koenig (Host)
And hopefully you're filtering those out to begin with when you're doing your outbound or even the inbound right, and so by the time your AE gets to that point, it gets to that sale. They actually don't get to that point because you have a qualified customer at this point. 

43:58 - Greg Strickland (Guest)
That's yeah, that you always aim for that level of perfection your lead scoring, your pharmacographic targeting and certainly in your named accounts. You're not going to have. You have enough understanding that you don't think you're going to get surprised at the end by some weird feature requests. But again, like every industry is different, like in the BI space, like people are incredibly nuanced in the type of charts that they want and the type of UI experience they want. So I feel and in the BI space the feature request list is long and it's real because people are incredibly particular in what they want to see. So I'm very empathetic that different industries and products have different requirements. 

44:36 - Michael Koenig (Host)
I am one of those customers. I have no empathy though for you guys, for the no, I kid, of course. Let's talk about empathy. You mentioned the importance of having empathy within different roles. What does that mean? 

44:53 - Greg Strickland (Guest)
Yeah, I think it just. It's really the acknowledgement that everybody's job is hard. It's just hard in different ways and I think if you can approach it that way, then I think you can reach a level of understanding and appreciation. Sales is very hard, but it's also like very rewarding. It's hard to hear no a bunch of times and then it's very rewarding to close a big deal and have everybody celebrate you. Cs is incredibly hard in its own way of having tough customer conversations consistently, which feels like a sales rejection almost, but then you celebrate the wins and when you've actually delivered a ton of value to a customer. So everything is like that engineering product design. They're all oriented and they're all hard in their own way and I think if you have empathy for that and you strive to have a better understanding of how they operate and how their gold and what they care about, then it goes a long way and you can make a lot of progress cross departmentally. 

45:46 - Michael Koenig (Host)
So I have empathy for engineers, because I myself tried to become one, which was so misguided. But I did learn some PHP and JavaScript and then I realized, wow, my brain does not work this way and this, if I continue down this path, is absolute folly. I got my hands dirty. I got a really great appreciation from that. But if we have AEs going off and, hey, let me learn JavaScript, that's not a path you want to go. So how do you create that empathy? Or rather, how do you connect the teams to develop that empathy? 

46:17 - Greg Strickland (Guest)
Totally so. One of the things that we're doing actually this month, later this month, is we have hackathons, like most companies do. Hackathons tend to be traditionally like engineering lead and maybe product comes along and you have these little pods and they go off and ideate and do something. What we're doing is we're actually like every pod for the hackathon is required to have a go to market participant, and so now you're having this ideation phase where you have a CS leader or you have a product marketing or maybe somebody on community or salesperson and you're building empathy, not only for the customers but also the process of what it actually takes to build product, and I think it's just seeing people do their work. 

46:55
There's really no, there's no easy answer. You can. I've been at companies where everyone starts in support, everyone's answering support tickets, everybody's responding to customer needs, and it builds a ton of empathy. Like you have to walk in their shoes and, yeah, we don't want sales people going and trying to crack together code, but if they work on a cross functional engineering team during a hackathon, they'll understand it a lot better and they'll have a. They'll have more empathy coming out of it. And the opposite will be true too, because the salesperson will be representing what's preventing them from being successful and how hard it is to navigate through a sales cycle that takes three, six, nine months sometimes. 

47:33 - Michael Koenig (Host)
I love that. That's fantastic. That's what we did at automatic both the hackathons, but also every new person who joined, regardless of if it was finance or an engineer. They all did three weeks of customer support and not only did you learn the product because you're helping people and you get to interact with your customers so valuable but support is a really hard job and you develop that appreciation for it. And then I love, through the hackathon as well, just having that sort of cross pollination and that exposure Time. For my favorite question, We've all had those moments where, as a COO or just anyone in a leadership capacity, something has come up and you have just been like I cannot believe that this is part of my life right now. I cannot believe that this is happening and I never thought I'd see that. Do you have one you can share with us? 

48:29 - Greg Strickland (Guest)
I tend to be a bit unflappable and it's not easy to surprise me but just having lived and worked in startup land, but there is a situation that sort of came to mind. There was a company that I worked with a while back and it was trying to build a business model to confluence of creating food, doing delivery, logistics and also technology, and so you can imagine like the harmony of cultures that is required in order to make that work. And we had an interview panel where we were trying to bring on another executive and we had the ranking system like everybody does right One, two, three, four and one was no, I will fight you if you try to hire this person. Two is like no, but I can be convinced. Three was yes, I can be convinced Otherwise. And four was I got, fight you, we must hire this person. 

49:16
And so seeing like, if you can imagine, like kind of Gordon Ramsay and Elon Musk in a room, like fighting over a candidate, it was a very, it was pretty surreal and it was that type of experience of the, the kit, the kitchen mentality, and this is my realm, this is my domain, like I own this decision. 

49:34
And then you have a CEO who's a tech person. Like what are you talking about? This is my company. And then you know it, like literally inserting myself into that conversation and calming down and having to explain to you know, a Michelin rated chef, that this is what it means for you to feel like a four, like you are fighting for this person because you fundamentally believe that this is true, but you're used to making all the decisions and shots in the kitchen and that's just not how this dynamic works. So, yeah, it was. Yeah, I don't know, referee, lifeguard, whatever analogy you want to be but navigated that through this like a two and a half hour conversation of just trying to get people with very different experience sets to come to the same plane and actually make a really important decision. That was wild. 

50:16 - Michael Koenig (Host)
I love that. I wish I was there. I wish I was applying on wall. It's actually. I knew one time that I was walking into a conversation that was going to be like that and I called my mom and I said mom, I'm about to walk into a conversation, people are going to be really nasty to each other and my mom goes. I wish I was there, yeah. 

50:38 - Greg Strickland (Guest)
I wish I was just observing too, but I was right in the middle. Yeah, I'm sorry. The chance to be referee. 

50:43 - Michael Koenig (Host)
That's fantastic, Greg. Thanks so much for sharing and thanks for coming on. Where can people go to keep up with you? And Product Board. 

50:51 - Greg Strickland (Guest)
Yeah, certainly, product Board has a number of different content and arms, and I would certainly follow us on LinkedIn. We produce a bunch of engaging sort of meme worthy content. That's always fun, and our blog as well. For me, I'm not a huge content creator, but if you feel like connecting on LinkedIn, we'd love to do that. And yeah, I appreciate you having me on here, michael. It's been a pleasure. Thanks so much. 

51:14 - Michael Koenig (Host)
Yeah, it's been a lot of fun. Well, thank you to you all for listening to Between Two COOs and a very special thank you to Greg Strickland for joining us. Tune in next time for our next COO chat on Between Two COOs and be sure to subscribe on Apple Podcasts, spotify or wherever you listen to podcasts, so you never miss an episode. Just visit BetweenTwoCOOscom for more and if you have a minute, please, please, please, leave us a review on Apple Podcasts and tell others about the show so they can get great advice from phenomenal COOs. Thanks for listening to this week's episode and until next time. So long.