Ep.264: Allison Pickens is the COO @ Gainsight, the company that provides everything you need to turn your customers into your biggest growth engine. To date Gainsight have raised over $184m from some of the world’s best VCs in the form of Lightspeed, Bessemer, Insight Venture Partners, Battery Ventures and Salesforce Ventures just to name a few. As for Allison, in her 5 years at Gainsight her list of achievements in endless from running all functions that drive value for Gainsight customers, now a 150 person team, to building out the corporate development function to being the right hand to the CEO. Allison is also an Entrepreneur-In-Residence at Bessemer Venture Partners and sits on the board of RainforestQA. Before Gainsight, Allison started her career in NYC with stints at Bain and The Boston Consulting Group.

Pssst 🗣 Loving our podcast content? Listen to the start of the episode for a promo code to our upcoming events!

In Today’s Episode We Discuss:

* How Allison made her way into the world of SaaS with Gainsight from her start in finance at Bain in New York?
* What does a strategic plan really mean to Allison? What is included in it? How should it be structured? In terms of ambition, how does one set ambitious enough plans to be a stretch but not a stretch too far? How does one tie their strategic plan to their financial plan? What is the right way to communicate this throughout the organisation?
* Why does Allison believe product marketing and customer success are the new sales and marketing? What have been Allison’s biggest lessons on how to effectively measure adoption? Who is accountable to this number? CS or product management? Does Allison believe that marketing needs to be held accountable to a number directly tied to revenue?
* How does Allison respond to the common negative of “services revenue”? What is an acceptable ratio of services to software revenue? How can one approach setting up a services team for scale? Why is having such a great CS team actually bad for product development in the long run? How can one mitigate this?

Ep: 265: Matt Schatz is SVP of Sales at WP Engine, responsible for defining and executing the global sales strategy. Matt has nearly two decades of senior leadership experience in sales and customer growth, specifically for technology companies with customers around the world including Bazaarvoice, CityVoice and Rackspace.

SaaStr’s Founder’s Favorites Series features one of SaaStr Annual’s best of the best sessions that you might have missed.

This podcast is an excerpt of Matt’s session at SaaStr Annual 2019.

Missed the session? Here’s what Matt  talks about:

  • Getting your “first story”
  • What is a lucky lead and how does that turn into predictable growth
  • Building trust across time zones

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin
Harry Stebbings
Allison Pickens
WP Engine

Below, we’ve shared the full transcript of Harry’s interview with Allison Pickens.

Harry Stebbings: This is the official SaaStr podcast with me, Harry Stebbings, at HStebbings1996 with two Bs on Instagram. You can head over there to provide feedback and guest suggestions for the shows. I always love to hear your thoughts there. But to our episode today, and I’m thrilled to welcome back a very special person to the hot seat. When this guest was first on the show over two years ago she was VP of Customer Success. Today she joins us as COO of the same incredible company, and so with that I’m delighted to welcome Allison Pickens, COO of Gainsight, the company that provides everything you need to turn your customers into your biggest growth engine. To date, Gainsight has raised over 184 million dollars in funding from some of the best in the business, including the likes of Lightspeed, Bessemer, Insight, Battery Ventures, and Salesforce Ventures just to name a few.

Harry Stebbings: As for Allison, in her five years at Gainsight, her list of achievements is endless, from running all functions that drive value for Gainsight customers, now a 150 person team, to building out the corporate development function, to being the right hand to the CEO. If that wasn’t enough Allison’s also an entrepreneur in residence at Bessemer Venture Partners and sits on the Board of RainforestQA. 

Harry Stebbings: However, you’ve heard quite enough from me and so now without further ado, I’m very, very excited to hand over to Allison Pickens, COO at Gainsight.

Harry Stebbings: Allison, it is such a pleasure to have you on the show today. As we said, it’s been two years since our round one, so, thank you so much for joining me for what will be a very special round two.

Allison Pickens: Thanks for having me back. It was great the first time and I’m excited for the second time.

Harry Stebbings: As am I. But, I want to get the ball rolling. For those that maybe missed our round one tell me, how did you make your way into the world of SaaS and come to be COO of the incredible Gainsight today?

Allison Pickens: Well, I’ve been at Gainsight almost six years actually, which in the realm of tech might feel like an eternity. But, because we’ve been through, fortunately, a lot of growth it’s felt like actually I’ve been through several different companies over my time at Gainsight. I initially found out about Gainsight and customer success because I had previously worked in investing at a company called Bain Capital and Bain Capital Ventures led the series B round back in 2013, so I got to know Nick, our CEO, through a Board member, as well as another Board member I got in touch with from Battery and really was excited about his vision, and especially about how there was such a notable secular trend in the rise of customer success.

Allison Pickens: As companies were shifting from on-premise software, perpetual license models, to the SaaS subscription model they were realizing, actually, that they would be making money over time, in triple, from their clients. Actually there was now a business imperative to invest in the client experience and ensure that these companies were avoiding a leaky bucket. I was excited about that growth in that market and about how actually there was now business imperative to do the right thing for your clients.

Harry Stebbings: I totally agree with you and I love the alignment there between kind of the company and the client’s success. I do have to ask, and I didn’t expect to go off schedule this early, but you mentioned the hypergrowth of Gainsight and how it’s almost felt like different companies in your tenure there. Can I ask, specifically with regards to the customer success function, how does that change and alter with scale specifically?

Allison Pickens: It definitely changes a lot. I like to think there are a few different stages for customer success, which actually map really nicely to David Skok’s model of a startup journey. David from Matrix Partners. He talks about in stage one of a startup, you’re looking to pursue product market fit, in stage two you’re looking to figure out your go to market, and then in stage three you’re actually scaling that go to market. In stage one, when we’re pursuing product market the customer success is really important for building empathy with your clients. Understanding truly what are their pain points and how can we evolve the product over time to address those pain points?

Allison Pickens: Often founders are building products for their own needs in the early days, but as they build their client base they realize, actually, it’s not enough to have that firsthand understanding with the pain point. Actually you need to truly listen to the pain points of your early clients. CSMs can be critical for that.

Allison Pickens: Then, in stage two, that go to market fit stage, it’s really important for your customer success managers to be thoughtful problem solvers, figuring out how to essentially automate their own work, optimize their workflow, and create a customer success playbook that eventually in stage three you can scale in a repeatable way.

Allison Pickens: Then in stage three we tend to see a lot more specialization. We see support functions cropping up, CS operations functions, sometimes account management, services become important. So, you tend to scale through greater specialization, selling services to offset the cost of your investment in your clients, and further automation through the product and in-app walkthroughs and things like that.

Harry Stebbings: I love that kind of segmented CS change through the stages. One thing that’s kind of prevalent throughout all the stages, there is the element of KPI setting, and really goal setting. When we spoke about it before you said about your thoughts on strategic planning at the company level, so I did want to start on this. What does a strategic plan really mean to you? I guess it’s quite a broad question, but what does it mean to you and what’s included in it?

Allison Pickens: Well, I’ll say strategic planning, first of all is super relevant to customer success, because strategic planning is the process by which you align all functions at your company around the most important priorities in your organization. In order to deliver successfully on the needs of your clients, you need everyone in your organization oriented around the customer. So, for all the customer success leaders out there, if you don’t have a cross-functional strategic planning process that’s working for you I would say this is a core thing that you should implement. To me, strategic planning, like I said, is about alignment and it’s about alignment around this essential unit of the OKR, which is not a term that I came up with. John Doerr came up with it and it stands for Objective and Key Result. Key result refers to a metric, a target, that you’re looking to achieve, and objective is sort of the more strategic, it’s the spirit of the metric, it’s the way that you’re going to tackle that metric.

Allison Pickens: An example of an objective might be, elevate the way that we are working as a company with our clients by selling to a higher-level buyer as measured by a key result or KR, which is the total bookings that we have at our company. So, notably I think at the highest level of your company the KRs should tie to the key metrics in your P&L. There might be a KR related to bookings, there might be a KR related to your gross margin, to your operating margin, and the objectives that you pursue will be tied to those KRs. Once we identify the most important priorities of our company, we also have to ensure that the primary focus of our team members is in line with those priorities.

Harry Stebbings: Totally agree with you in terms of that alignment and the importance of it. Can I ask, how does the creation of OKRs look like to you in terms of who’s involved? How long does it take? What’s that actual process in terms of the setting of them themselves?

Allison Pickens: Well, I can’t say that we’ve 100% mastered this at Gainsight. We have had our strategic planning process for a couple of years, but this has been the first year where it’s been a really big focus for us at the granular level, so we’ve learned a lot along the way. I think there are a couple of key components to creating a great strategic plan. One is you need that feedback from across your organization on what’s going well and what’s not going well. Some people might call that bottom up feedback. If we truly believe in inverted organizational structure where actually leaders are servants supporting the rest of their team, then perhaps the team members are on the top, leaders are on the bottom. In any case, we’re trying to gather feedback around the organization on what’s going on. That gathering can be conducted through round tables, off sites, through anonymous feedback forms, and other types of feedback-gathering mechanisms that should be conducted on an ongoing basis in, I think, a really healthy company.

Allison Pickens: In addition, often there should be some sort of forum where the extended leadership team can get together and talk about what they’re noticing in the business. Then from there, you want to make sure that you are designing a strategic plan that’s also in line with your financial objectives, so there’s often an iteration process between the strategic plan and your financial plan, as well. Very important that they’re tied together in that as part of the strategic plan you decide that an initiative is going to be super important, but actually in your financial plan you don’t have the budget to invest in that initiative. Obviously that’s going to create some issues down the road.

Harry Stebbings: Totally. I absolutely agree in terms of that resource allocation constraints. I do have to ask though, in terms of the actual planning themselves really more with the key results where you’re driving towards certain tangible metrics, how do you think about setting key results that are both achievable and challenging, but also won’t cause massive disincentive and real kind of damage to the team morale if not hit? How do you think about striking that balance?

Allison Pickens: This is a really important question. There is a type of metric that could be called a moon shot, which is, it’s a shot in the dark. You’re doing your best to achieve something that is unlikely. It’s high risk but it’s high reward. In situations like that it’s important to note that that number is a moon shot, and you might actually compensate your team members, not on that number but on some other basis, for example on whether they’ve achieved objectives that are more within their control.

Allison Pickens: There’s another kind of key result which you could call a roof shot which is, you know the roof is within reach, it’s something that we can achieve and, therefore, we need commitment around it and it might be that compensation and other forms of performance management are tied to that roof shot. There are also situations in which a metric might be something that we believe to be important but we haven’t measured it in the past so we don’t have historical knowledge about what level of that metric is achievable. In those situations, what I recommend is starting to track the metric for a period of time to get a baseline and then after that, using that metric as a KR.

Harry Stebbings: Can I ask, once the KRs are displayed and then we run through the process and, as a result whether we’ve hit it or not, how do you think about doing a postmortem post, either successful or not? Do you do it on both sides of the equation if successful and if not successful, and what does that structure for the postmortem look like?

Allison Pickens: Definitely. During the quarter when we’re tracking progress against our KRs, we always want to make sure that when forecasting to be below our key result, the target, that we have an understanding of why it is that we’re forecasting lower than the target, what’s actually driving that? Similarly, if we’re forecasting above the target, we want to know what’s contributing to that success. So, we have postmortems, which I’ll get to, but we also want to make sure that we’re actually learning along the way.

Allison Pickens: In addition, when we’re forecasting below a KR during the quarter, we want to make sure that we have what we call a path degree to actually achieve that target. A path degree can actually be a simple waterfall chart where you’re showing what are the steps that you need to take that will contribute to meaningful improvements in that KR up until the target. Then, at the end of the quarter, once we’ve actually deemed where we landed relative to our KRs, we want to, as you said, do retrospective and a learning. One of the things we started doing recently is following the Amazon model, but more of actually writing up Word documents about layout, what we learned and why. Sometimes actually writing something is a forcing function for testing your understanding. It can be pretty easy for anyone to put together a slide, but it’s a lot harder to actually write what you’re thinking.

Harry Stebbings: I totally agree with you. I think my kind of thinking definitely where making investments in doing memos exceeds just kind of normal thinking when you do the memo itself and write it down. But I do want to continue, though, with the theme of kind of expansion across the org. We chatted before, and I titled this next element, When Product Management Marries Customer Success. I thought that was rather brilliant of a title, I have to say. But, I do want to talk about the integration of the two.

Harry Stebbings: What makes you say about this incredibly close alignment between product marketing and customer success, almost similar to that of sales and marketing before? What was driving your thinking here?

Allison Pickens: Definitely. I think there’s always been an essential collaborative relationship that needs to take place between customer success and product management, but I don’t think anyone fully realized how married these two functions need to be in order to drive the success of the company until recently. So, we do like to think of product management and customer success as being the new sales and marketing. It’s driven by both sides. In customer success we tend to see a very important gain point, which is that these teams are trying to figure out how to scale. Now, the most scalable asset in your organization is the product itself, so we find that in customer success teams where the CSMs are plugging gaps in the product by creating workarounds and band aid solutions, they have an opportunity to work more closely with their product teams to help the product team fill those gaps. That way the customer success team can spend less of their time on the technical troubleshooting, the band aid solutions, and more of their time fostering the path to renewal, to success, and in even helping to drive expansion over time.

Allison Pickens: Now, from the product team’s perspective, often the number one pain point is knowing whether you’re building the right things, getting greater confidence around your roadmap. The customer success team has a wealth of information that can be valuable. Now, interestingly, from the product team’s perspective, the customer success team is not often sharing feedback and using language and in a way that tends to resonate with product teams. I tend to find that customer success people are often situational thinkers. They’re very good at looking across the situation and all the people involved, the product features, the different dynamics, and understanding holistically what’s going on with the client.

Allison Pickens: The product teams don’t tend to think about problems on an individual client-by-client basis. They’re more systems thinkers, looking all the way across a client base and looking at the trends. So, I think customer success with a situational thinking can point to anecdotes and hunches that the product team can then explore in terms of developing hypotheses or detecting trends. So, both of these functions truly do need each other and I think we need to create better processes and systems for allowing them to collaborate.

Harry Stebbings: I totally agree in terms of the need for seamless collaboration between the two. I actually had a guest on the show recently that said something very interesting. He said, “I don’t actually think that customer success should be amazing, because if customer success is too good then they will cover up blind spots in product that need to actually be solved by product.” How do you think about this? Is that actually pretty unfair and it’s solved by seamless communication between the two, or do you think he’s actually got a point in terms of they can’t be too good to cover blind spots?

Allison Pickens: I absolutely agree with that. I do think that, and I’ve seen it actually on our own team at Gainsight, sometimes when the customer success manager takes so much ownership, they run the risk of solving the problem in a way that’s not scalable. I think what we need to do is redefine what it means to be a great or amazing customer success manager. Perhaps amazing customer success managers don’t try to own the problem entirely on their own, they see part of their job as relaying feedback to the product team, who can then help create an ever better product experiences and also help that customer success manager scale their job even more.

Harry Stebbings: I’m totally with you in terms of that scalability. Speaking of scalability, though, and one way that a lot of people think about scaling CS today is through ABM in a way, but pushed down through the funnel. How do you think about using content as a scalable method of customer success today? Is that central to your thinking or actually it’s still removed from the core customer relationship?

Allison Pickens: Content is really important. Historically, content usually took the form of PowerPoint presentations that a customer success team would share with its clients, perhaps in executive business reviews, or best practice sharing sessions, historically often took the form of knowledge-based articles. Over time, we started using online communities, so there’d be wealth of content built up there, largely by your clients. More recently we’ve been seeing in-app walkthroughs as being an important venue for distributing content, and I think that’s often the best way to do it. Share content with your clients when they need it in the place where they are operating, which is your product.

Harry Stebbings: I love that in terms of in-app walkthroughs and actually I haven’t seen that as much, so that’s super interesting. To me you’ve got in-app walkthroughs, and a driver for both functions, essentially, is driving adoption and increasing adoption. What’s been your biggest lessons, Allison, on how to measure effective adoption? It’s not actually as easy and simple as it seems.

Allison Pickens: It’s not. I think one of the biggest challenges and also opportunities for companies is to identify what’s that north star adoption metric that we’re all aiming for. It might be number of times that your clients are completing a certain high value action in your product, and by the company you might want to see the volume that those actions go up over time. It might be the best proxy for the health of your client base and also the growth of your company. Often as well, that north star metric actually drives the pricing model. For example, in more consumption-based pricing models within companies, so actually that north star metric truly could be a revenue driver as well.

Allison Pickens: Now, once we’ve identified the north star metric, the question is how does it apply to the work of customer success and also product management? In customer success, we’re often looking at problems and opportunities at a customer level. The more customers that we move to the direction of health, the better. It’s a risk sometimes, actually, if we’re looking at total aggregate volume of a particular adoption action and customer success, because that volume might be concentrated in only a couple of clients so it may not actually represent whether your client base as a whole is healthy. What we need to do in customer success is create a health score which is based on that north star metric. Essentially we’re trying to move as many clients as we can into the green level of that health score based on that north star metric that that particular client is representing.

Allison Pickens: Then, on the product side, product managers tend to think about adoption metrics more on a feature level or a module level, so in that world of product we might want to look at how do we contribute to that north star metric through the appropriate adoption of specific features?

Harry Stebbings: Can I ask, in terms of the accountability, do you have split accountability then between the two different functions of products and CS? Is there a unified accountability metric that one is driving toward? How do you think about kind of effective accountability establishment with product and CS?

Allison Pickens: I do see many companies actually increasingly having joint accountability for that north star metric across the two functions. That can sometimes create great collaboration. On the other hand it can sometimes create a dilution of accountability, particularly if you don’t have the right culture. So, in that situation I think it can be valuable to have two different contributing metrics for each of those two functions. For example, in customer success, the primary metric might be the average health score across our client base which, as I mentioned earlier, could be driven by that north star metric. Whereas in the product organization the metric might be more oriented towards measuring the ROI of a new feature release, or the adoption of the product overall.

Harry Stebbings: Got it. No, that makes total sense. I think I can get my head around the segmented accountability more easily. I do want to touch on one element there that I spoke to Nick before the show about, and I would love to have more context on this because he left me with a cliffhanger. He said, “You have to speak to Allison about creating elements as a prescriptive CS methodology.” He left it there, very kindly of him. Tell me, what did he mean by this and how does that come into the fore with your thinking today?

Allison Pickens: I love that cliffhanger. So, what he is referring to is the elements of customer success that sort of a knock off of the periodic table in chemistry, which some of us might remember from high school, or maybe later if we were particularly interested in the subject. We created the elements of customer success based on tons of conversations we were having with customer success leaders across the industry, understanding what their pain points are. Each element is a pain point or objective that a customer success leader might have. Over time throughout these conversations we’ve built up all the best practices that allow you to actually fulfill that objective, or element. Now, what’s interesting is that these elements are mapped to different stages of maturity in customer success. So, as you move from one stage to the next by rolling out these elements, actually you achieve very meaningful improvements in gross retention and net retention.

Allison Pickens: As you move from stage zero to three you achieve a 13 percentage point increase in gross retention on average and a 33 percentage point increase in net retention. So, there’s a lot of data to support that rolling out these elements is a good idea.

Harry Stebbings: I absolutely love that. Is it actually a periodic table that you’ve created? I mean is it structured in that way?

Allison Pickens: Structured that way, yeah. Actually you could Google it, and you’ll see it.

Harry Stebbings: I’m excited to Google it. I haven’t seen that before. I do want to finish, before we move into the quickfire, on a topic that I’m super interested by, because I speak to, obviously, a lot of investors on the show, and a lot of them when I speak to them about services revenue, they pull this face and then stress some form of concern or another. I want to ask, how do you feel about services revenue and is it always bad?

Allison Pickens: I think services sometimes has a bad name in the SaaS industry. We are software people. We’re trying to automate things, create technology that scales. I think the reality is that sometimes we underestimate the value of human interaction with our clients both in and of itself but also for learning purposes so that we can know what to build in our product. Now, what’s tricky is that sometimes it’s hard to actually invest in that human effort that can contribute to learnings and also greater outcomes for clients beyond what the software can do out of the box.

Allison Pickens: So, in situations like that it’s beneficial to us to sell services merely to offset the cost of that human investment. We’re not looking to create a super profitable services business, especially in the earlier stages of the company, we’re merely looking for ways to sustainably invest in that kind of human interaction. What I recommend is, when you’re in the early stages of a company, even if you’ve got a self-serve model, have people on your team, including the executives, but also customer success folks, services folks, who are reaching out to your clients to listen, understand how the product is solving their pain points, or not, and then feed feedback to the product, as we mentioned earlier. As you grow larger … When you’re serving small clients, your products should start to automate that human work and automate the services away, so that you don’t have to sell services to your clients.

Allison Pickens: Now, on the enterprise side, actually services can be a very interesting lever for driving higher renewal rates and also driving expansion. In enterprise, especially, clients are often looking for advisory help. They want the vendor to truly be a thought leader on overall their strategic objectives not just on solving tactical problems. If you can frame yourself as being a strategic advisor to a client through advisory services, you will likely sell more software.

Harry Stebbings: So I’m totally aligned to you in terms of the benefits in terms of retention, upsell, what it does for product evolution, and kind of those feedback loops. I guess my question to you is at what stage does it become an unhealthy ratio of revenue and where’s the balance between the two? Is 80/20 the right split between kind of software to services? What’s your thoughts on the degree to which it’s good?

Allison Pickens: I think it really depends on the company, and I know Tomasz from Redpoint actually has produced some interesting analysis about attach rates and services and how they compare with valuation. So, I’d recommend actually looking up some of his blog posts on that. What I would say is, even though it does depend on the company, I think in the enterprise, based on what the data that I’ve seen, it’s quite normal for enterprise-oriented companies with more complex products to have attach rates that are north of 50%. What that means is you’re selling 50 cent services for every dollar of subscription revenue that you bring in. Then, on the SMB side your attach rate might be zero, or it might be 10 or 20%.

Harry Stebbings: Got you. No, that totally made sense and I love Tom’s writing on it. We mentioned like upsell and adding extra juice to the revenue stream there. I do want to talk about one final element before the quickfire there, which is another way to add extra juice to the revenue which is, obviously, expansion of product line, something that you at Gainsight have done incredibly well. I’d love to hear your learnings on what the journey has been like from a single-product company to a multi-product company. What have been some of those learnings and takeaways for you from that transition?

Allison Pickens: Great question. I think a lot of companies are grappling with how do I handle customer success especially, and also sales, in a multi-product environment? For us I think there have been a few things that have been critical to our success in the transition. One is having a holistic framing of your products and how they work together. We don’t want to be holding companies, we want to be software companies where the products mutually reinforce each other, there are benefits to a client from using multiple of your products beyond just the siloed value that they get from each product. So, having sort of a holistic framework explain how these products relate to each other and how your clients should consume these products over time, perhaps a long maturity curve, is very valuable.

Allison Pickens: The second thing is that you want to be really clear on your organizational structure and how it’s equipped to sell, and deliver, and build multiple products. When you’re starting out with a given product line, it can be valuable to have specialized teams that are building, selling, and delivering them. That ensures that you have a focus group, that this product isn’t diluted by your core business, by the focus there. It ensures that you have a core team that can learn over time on what’s required to make this product successful. Assuming that you choose some initial success, at some point you want to integrate that specialized team back into your core business.

Harry Stebbings: I am totally with you. Can I ask, in terms of the integration back, are there some core challenges that you faced, or maybe you see others facing in the ecosystem around you, that you think should be highlighted.

Allison Pickens: I think it’s important for folks to understand the timeline for having a specialized team and the intention in the long run to integrate. For example, your core team needs to understand that this other team is a specialized team that needs to be supported, it’s not meant to distract the core team. It’s to the benefit of the core team to have the specialized team and that over time greater collaboration will be created. I think the communication around that is very important.

Harry Stebbings: I do agree with you in terms of that communication. I do want to finish on, my favorite element, as you know of any episode, being the quickfire, Allison. So, I say a short statement and then you hit me with your immediate thoughts. Are you ready to rock and roll?

Allison Pickens: Let’s do it.

Harry Stebbings: How often should CS check in with their customers? What’s the right cadence?

Allison Pickens: It definitely depends on the segment and your product. I would recommend having a cadence for executive business reviews, stakeholder alignment calls where executives from your company are talking with executives at your clients’ and also separately a process for reaching out to your clients when the data warrants it, when adoption is heading in the wrong direction, or the right direction and you’d like to ask for some sort of an advocacy engagement from your client.

Allison Pickens: But, in general I would recommend letting your touch basis with your client be informed by a success plan where you map out the objectives the client has and then together you come up with a plan of action for pursuing those objectives. So, instead of having a lot of recurring calls, we should be letting the success plan drive the touchpoints.

Harry Stebbings: Hedgehog versus the fox. Which one are you Allison?

Allison Pickens: I love this. Do people have context on hedgehog and fox? Do you want me to explain that?

Harry Stebbings: I have absolutely no idea myself, so I would love some context.

Allison Pickens: It sounds like Nick asked you to do this. That’s the basis.

Harry Stebbings: This was Nick.

Allison Pickens: Amazing. So, Isaiah Berlin is a philosopher who wrote an essay about the distinction between a hedgehog-type thinker and a fox-type thinker. The hedgehog has one defense, which is their prickles. So, hedgehogs tend to think about the world in terms of a unifying single framework. Foxes, on the other hand, see the complexity in the world. They see the world in terms of its multiplicity, there being many things. I would call myself a fox with aspirations of being a hedgehog. I see all the different complexity and my constant pursuit is to try to synthesize all the complexities of the world into that single framework.

Harry Stebbings: If on a tight budget, how should one staff a CS team?

Allison Pickens: If you’ve got a tight budget and you’re a startup, I recommend having a dual role between product manager and customer success manager. That way you have a single person who is gathering feedback from your clients, learning from the client experience, and then trying to improve the client experience by building better products.

Harry Stebbings: What would you most like to change about the world of SaaS today, Allison?

Allison Pickens: What I would love to see is a SaaS industry, and tech industry more broadly, that’s focused on building what I call human-first products. I think often we build with the goal of higher engagement, more users, greater conversions, scale. I think we need to put the humanity back into the products that we build. Actually, I’m not the first one to say this. Caterina Fake has actually been saying this for many years and I think it’s a really important mission that we should all be adopting.

Harry Stebbings: Allison, it has been such a pleasure to have you back on the show. Thank you so much for putting up with my dulcet British tones for one more episode kindly. It has been so much fun.

Allison Pickens: Thanks, Harry. This is great.

Harry Stebbings: Absolutely love having Allison on the show. If you would like to see more from Allison, you can find her on Twitter @PickensAllison. Likewise, it would be great to welcome you behind the scenes here at SaaStr. You can do that on Instagram at HStebbings1996, with two Bs. It’d be great to see you there. As always I so appreciate all your support and I can’t wait to bring you another fantastic episode next week.


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