How To Make or Fix Your 2026 Annual Plan with Jason Lyman, CMO of Customer.io | Ep. 373

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0:24Welcome to the Marketing Millennials, the no BS marketing podcast. I'm Daniel Murray and join me for unfiltered conversations with the brains behind marketing's coolest companies. The one request I tell our guests, stories or it didn't happen. Get ready to turn the f*** up. We are back with another episode of the Marketing Millennials podcast. I'm here with the chief marketing officer of customer.io, Jason Lyman. I'm excited to chat about annual planning. I think this is a good time to chat. We're approaching end of year and you might have made mistakes if you've already done it, or you might need to fix some things right now, but I hope this conversation will help.

1:13But I want Jason first to go into like, explain your background a little bit, how you got into marketing, and then we can get into the detail. Perfect. Well, Daniel, thank you for having me. Yeah, just a little bit about me. I actually didn't start my career in marketing. I spent about four and a half years working as a strategy consultant. So maybe that's a little bit about why I have a passion for planning and strategy development. But over the course of four and a half years, I spent a lot of time working with media companies who were being disrupted by new media technology. So this was a while ago.

1:46This was back when streaming was this new thing. The iPhone had just come out. Free-to-play games were blowing up. Through a lot of my casework, I was able to see firsthand the power that technology could have on end users, on business models. I knew that I wanted to work in tech and try to drive innovation forward by working more closely with products that are really pushing the envelope or experimenting with something new. I decided to go back to grad school and did two years at Berkeley and use that to transition into tech. So my career spanned both kind of big companies and small. So I started my career up at Microsoft working in the Office 365 group up there.

2:25That's kind of where I learned how to market and sell a SaaS solution, learned what marketing looked like at scale, but also kind of realized that I wasn't a big company guy. I kind of wanted to go places where I could have more ownership, more direct impact. I was lucky enough to join Dropbox pretty early. There, I was the second product marketer and worked through the IPO. So I saw multiple stages of growth and maturity. And that really seeded my desire to work in the high growth phase of a company's maturity. So since then, I've worked at a handful of startups. And most recently, I currently serve as the CMO here at Customer.io.

3:05Fun fact, I was actually a customer of Customer.io at Dropbox, Podium, BetterCloud, and Ethos. So the four companies I worked with prior. So I was able to kind of know firsthand the power of the platform. But as an outsider, I saw a lot of potential from how we think about our overall marketing strategy. And so that's really what drew me to the role. And I've been here about almost three years now. And so it's been an amazing ride during that time. Yeah, I always found that you could find really good marketers if you just get bringing in a customer who's like really understands the product and really understands how to use it as the marketer it always becomes some of the best employees in your company like people who actually love and have passion for the product but i want to go into something that is happening right right now was happened a month ago but or as people are still doing it, but I think a lot of people annual plan for the next year of marketing, but you think of it as more of a way of being a growth engine for your company.

4:12So what is the number one mistake marketers make during the planning that immediately limits their growth potential? Yeah, I think for me, you need to make sure that whatever marketing strategy you develop is connected to the broader company strategy and where those priorities and goals are. Because it can be failure mode for a marketing team if their approach is built in a silo and their plan doesn't take into account some of the goals or metrics that the broader organization is trying to achieve. I think a really tangible example that a lot of teams might face is there's a lot of excitement, for instance, around a new product investment and that EPD is really putting a lot of resources behind.

5:02But then the equivalent go-to-market investment to drive the launch of that isn't built into the plan. And that then creates this disconnect. I saw this firsthand when I was at Dropbox. We were building, at the time, Dropbox Paper, which has a lot of similarities to Notion today. And we had made a lot of great progress as far as some of the desires of our earliest adopters. And we wanted to make this a really big swing and an anchor of our broader marketing strategy for the second half of the year. But we didn't align early enough in our planning process to have the budget necessary around promotion, having the right level of investment in our PMM resources to support this evolution and storytelling that was required.

5:56And so for me, it's one of those examples that I go back to pretty regularly. And it speaks, I think, to me at least, the importance of having that conversation and connectiveness between what you want to do from a company perspective and what you need to be doing from a marketing perspective to really support the broader goals of the organization. I want to go high level first, and then we'll go deeper and tactical of how other people could do it. But I want to start with what does it look like as a CMO to start the annual planning? What questions do you ask the CEO, the board, whatever, to make sure you start building the correct plan for 2026 or the next year?

6:42Yeah, so I use a framework that I've seen that I've had a lot of success with that is the play to win framework. And as part of that, there's a few questions that you have to answer as a part of building that out that I think translates into a pretty tangible set of outcomes and actions that a marketing team can rally around. So the framework really starts with this concept of what's our winning aspiration. And so it really kind of anchors the broader goal and the broader team around this aspirational goal that we're going after. The next question is, where will marketing play? And so that really helps anchor the team around who is the ICP we're going after?

7:30How big is that audience? What are the characteristics? Where are they located so that we know where to try to find them as we go out into the world with our broader communication approach? The third question then is, how will marketing win? And so that then becomes a question around what are the opinionated things that we believe as a marketing team we need to be doing to reach that audience and drive action from them. And I like to think about these as marketing's strategic pillars for the year. And so these tend to be three to five opinionated statements around what we feel like we need to do or where we need to invest most of our time, energy, and resources.

8:15And then the fourth question is, well, what capabilities must be in place to deliver on that winning strategy? And so then you can then take those core strategic pillars and decide what are then the specific activities or actions that you need to take to deliver on those strategic pillars. And so then it starts to really break down what is a higher-level approach into more tangible sets of activities that the team can then really rally around. And then the last question that you need to ask yourself is, what are the management systems required? And so this is where you can then align resourcing and any new headcount request.

8:59Budget, what do you need to invest in from software and programs perspective to deliver those activities that you've outlined to make sure you can execute on the strategic pillars that you have. So it allows you to build that operational plan to support the broader kind of strategy that you've just developed as a marketing team. And so if you have alignment around those five questions, then it becomes a really easy conversation with the CEO or with your peers across the organization because they can then see how your work ladders or connects into the broader work that the company is trying to deliver.

9:40So that's at least, I think, a common framework that I've used and found a lot of success with to drive that alignment at the company level. Yeah, I think that's a solid framework. And I think it's great to put aligning CEO, other stakeholders that are the same, because that's probably one of the most number one job of a CMO is making sure that all the leaders on the same page and making sure marketing is in the talks of every room. But I want to also go into, as the CMO, once you've made this plan, what are you looking for your leaders under you to build to make sure that it fits your plan? So what does it look like when you say, okay, here's the question if I've answered.

10:26Now I'm with my VPs or SVPs or whoever's under you. What are you looking for them to build to make sure that they hit that ultimate marketing goal? Yeah. So two concepts here that I think are important. One is driving towards multi-level alignment. So that plan covers everything that marketing is going to be doing. And so that plan then needs to be communicated from the CMO to their peers, like the CFO or the CRO. And then similarly, I want my leaders that report into me to be having similar conversations, but with a mind to what aspects of that plan are their cross-functional partners most interested in.

11:15So my head of demand gen needs to be having a similar conversation with the VP of sales that's over AEs and BDRs. Or the head of product marketing needs to be having an equivalent conversation with the VP of product around, hey, here's the marketing plan, but these are the pieces that you should care the most about. And are these the things that you believe we should be kind of focused on? And then I think you can even go a layer deeper than that where, you know, maybe individual like ICs are communicating with kind of their peers that they're working with and making sure that they're bought in.

11:57So, you know, you almost have this kind of layer cake of alignment that needs to be articulated. And then the second concept that I think is important is strategies can sometimes feel a little bit broad and ambiguous as far as what does that mean to me in the short term. And so you need to then lean into the kind of operating rhythm that you have around planning and start to translate that into what does that mean in the short term. So my teams, we tend to use OKRs. And so I like to pair together the annual plan with, hey, this is what our Q1 OKRs actually look like so that you're able to then see and practice what does this mean?

12:42What are the commitments that we are going to deliver? What are the core results that we are looking to drive in the short term? And so that starts to make the plan become more real for those cross-functional partners when you're able to pair the strategy with a set of OKRs or, again, whatever your monthly or quarterly kind of planning cadence looks like, that then drives conviction and understanding around the approach because you're able to make it more real and more tangible for them. One question I also have is a lot of annual planning is always based on like historical, like reporting, historicals, historicals, and historicals.

13:23So how do you like bake in future opportunities that have not been like proven by historical? Because obviously you can forecast based on this is what we're going to do and expected revenues, expected ops. But there are some things that are swings that you're going to do that there's no historical based data that you can prove. But how do you how do you bake that into the plan to make sure that you're telling the right story that we should take this one big swing for the next year? Yeah, so two things I think that I'll kind of add here is maybe mental models to help. So the first one is, I've used this framework before, but it's the 70-20-10 framework.

14:08So 70 % of the commitments that you have as part of a strategy should fall in this higher confidence bucket. So you don't want to bet the farm on a strategy that you feel like has a lot of beta in it, where there's these big upsides, but also could potentially have big downsides. You want to anchor around the things that you know are working, but then you need to make sure you're allocating 20 % of your time and budget towards things that are medium confidence, where they have these higher upside associated with them so that you're able to have this opportunity to really kind of overperform what you're currently planning And that's what drives motivation, kind of excitement.

14:58And also, too, it's the only way you learn enough to really continue to augment your approach. And then the last 10 % should be in these lower confidence, but truly game-changing bets that you're trying to make. And so that allows enough... To me, the risk-reward trade-off feels really strong when you allocate a portion to activities that would maybe fall in that bucket. And so I think that that's one way to drive that mental model of, hey, we want to do some things that are outside of the norm, is if you think about your budget and you think about your time spent and making sure that they loosely align to this breakdown.

15:45I think the second thing that you can do here is, a lot of times, people get in the habit of just rolling over the budget, for instance, that they had last year, where it's like, hey, this is what we did. We know we're going to have 10 % more. So do we just start to grow things at a roughly equivalent rate year over year that aligns to the overall number? And what I've really tried to push my teams to do is to have it effectively build it bottoms up every year. So that way you're looking at every line item that you have and assessing, is this something that I trust in, that I believe, or is this something that maybe isn't quite working or the performance has started to decline?

16:31And as a result, I want to reallocate that budget to something else or something new. And so I find that that kind of, starting from effectively a zero basis plan and then building up from there tries to control a bit more for getting into the same rhythms, and it forces you to assess each line item and decide, is that something I want to double down on or not? And so I think those two mental models can kind of get you out of the loop of doing the same things over and can incentivize more experimentation as a broader team. Yeah, I also want to ask you, because a lot of annual plans die after like a q1 q2 because everything market happens the marketing happens things happen all the time in marketing i get thrown and you don't know this happens in the market this happens in the market but how do you want like build in flexibility to make sure that okay if something if something goes wrong in my annual plan we have backup plans we know we could shift instead of being, I've been in companies where it's so rigid that we were not going off the plan, even though we're headed down that wrong road, because that's the annual plan and we're not going to shift away from it.

17:50Yeah. So for me, the thing I want to kind of keep consistent is these high level strategic pillars, because hopefully there's enough conviction around, hey, these are the core investment areas that we believe will drive the impact that we're looking for. But the way to achieve those pillars has a lot of different paths. And so I really try to make sure that I feel conviction around those pillars. And then that's where you need to pair the annual planning process with a really strong either monthly or quarterly planning effort, because that allows you, that builds in the agility that you can change things or tweak things every quarter or every month once you've started to learn things.

18:42And so that allows you to change your path or change your course if you learn something new or if things are kind of going off the rails. And so I think that that pairing kind of works really well. You know, another concept that you might think about is when you think about metrics in particular, because a lot of times that's where, you know, marketing gets a lot of pressure to perform. You know, think about what metrics are your KPIs versus what metrics are your OKRs. So I think about KPIs as like 100 % we can't miss these metrics versus OKRs. Those are ones where they can be stretched. They can, you know, change quarter over quarter.

19:25You know, you can adjust them as you learn more. And so that way the team stays focused around, look, we're not going to miss on revenue. We're not going to miss on pipeline. We're not going to miss on MQLs. But the things where we have flex on is maybe some of the performance of different marketing channels or the impact of different product launches. Like, you know, those can be OKRs and be things that, you know, we set these ambitious goals on or they're things that can honestly drop out of a plan if they're not working. And then the last thing I would say is, this is where you need to have a tight relationship with your finance partner.

20:03So if things are going off the rails and things aren't aligning, then you need to be driving as a marketing leader, a CMO, a VP of marketing with the CFO to be like, look, there were some inherent flaws in the financial plan that we built. Let's take a step back and reassess. And so I've been at companies where we've re-forecasted things after six months to better align with what expectations should be. And then that then cascades through the plan that marketing has for the second half of the year. So as long as you have that open, transparent conversation, you can more effectively navigate some of that complexity that you might face when headwinds arise.

20:48all right this is a two-fold question but how has ai helped you do annual planning um because this is the the question that probably you'll get a lot and then what are some things that are built into your plan that are this would say like ai first principles that we your team should follow to help them be better to help hit the goal so one is like how you used it to plan and how are are like AI first principles that people can use to be better at their, hit those OKRs? Yeah. So the first, the first, so for the first question as far as like how AI is like kind of helped out that process, I think one has been through just the helping streamline the synthesis of data that we've gathered throughout the year that should then inform what we think our priorities should be next year.

21:41So whether that is, you know, working through the summary of performance data across the funnel, or whether it is amalgamating a bunch of customer feedback that we've gathered from all of the sales calls and customer case study interviews. And so that way, we're starting with a really solid foundation of here's all the data inputs that we believe should inform the strategy. The time to collect that and synthesize that into takeaways has been kind of dramatically reduced. I think the second way is that it helps to stress test some of the opinions that you developed as part of the strategy development process and helping you assess if there's anything that you're missing in that.

22:30So it serves a little bit as kind of a validator of, well, have you thought about this piece? Or what about, you know, this feels in conflict with some of the data that you provided as part of the collection process. And so it really helps you build conviction and refine your point of view. And then third, it helps with the synthesis and content creation piece of that. So translating what can be discussions and design thinking efforts as a marketing leadership team into the tangible outputs that you're then going to be sharing with your team and cross-functional partners. So those are three ways in which it streamlines, shortens, and hardens the process.

23:19And then as far as how to use AI to future-proof the strategy and what you want to do, one of the key ways that we've done it as a marketing team at Customer.io is one of our strategic pillars is around investing in our marketing foundation. And we have dedicated activities around investing in different tooling, like building out the right workflows to enable AI adoption more easily. We're building into our plan commitments to rethink the way that certain processes work with AI in mind at streamlining that process. And then additionally, we've pushed ourselves when we have headcount requests. Are those headcount truly needed or can we leverage AI to push out those hires or replace those hires?

24:19Those are a few ways in which we're kind of building it into our normal planning rhythms so that we're staying ahead and making sure that we are kind of AI first and how we think about our marketing strategy. And I wonder, because you said that you've used Customer.io at four other roles before. So I want to know how to best use a tool like Customer.io for annual planning. What are you doing? because I'm pretty sure you are in Customer.io here as well. You're using it. So how should people best use Customer.io to do annual planning and how has it helped your process be easier and make better decisions?

25:05Yeah, so for those that aren't aware, Customer.io is a customer engagement platform that allows teams to create automated customer journeys that engage and convert. And so we're used in common use cases around onboarding, activation, retention, cross-sell, up-sell. If you're doing any marketing in those stages of a customer's lifecycle, you could benefit from a tool like Customer.io. So our team has dozens of campaigns set up at each of those stages to try to drive our leads and customers through everywhere from onboarding, activation, retention, and then we use it to drive engagement to potentially upsell them into our premium plans and they have to interact with our sales team.

25:56And so as part of our planning process, we're actually going through all of our campaigns that we have set up and assessing the impact around what's working and what's not working. And thankfully, inside of Customer.io, we have an AI assistant that can help to do that at scale for us. So we can actually query the AI assistant to look at relative performance of different campaigns, and it can kind of come back and let us know this is what's working and what's not working. And so we're able to then suss out using AI capabilities in our platform to identify where we believe opportunities exist as we think about the kind of life cycle investments that we're making.

26:43And the performance of those campaigns as far as what's working, what's not working, serves as an input into our broader annual planning process. And so that is at least a high-level way of how our tool provides the necessary data and feedback to inform some of our decision-making from a marketing perspective. I mean, this is another way to use AI too, which I mean, your tool has it. And I think if your goals are to improve these metrics, a lot of those lifecycle metrics, this is definitely a tool that is really great at that and inputting data and easy to use and flexible. But I also want to go into another question too, because I think it'll be helpful to marketers listening.

27:27is what are some ways that like successful ICs or successful managers could go into annual planning to like help them accelerate in their career? Like what have you seen that you did to accelerate your career too that helped you win when it went to annual planning time and then hitting your goals and making sure you set up goals to help you win and be seen in an org? We are all marketers here. So I'll say it. I hate batch and blast messages. It's not 2010 anymore. We've got data. Let's actually use it. That's why I love customer.io. It helps you turn first party data into personal messages across email, SMS, and push.

28:06Build it, automate it, and make it not suck. Start a trial and join 7 ,800 plus brands already doing smarter marketing with customer.io. Visit customer.io to start your free trial today. Yeah. So I think the best strategies are ones that come together through top-down thinking and bottoms-up thinking. And so a lot of times the marketing leadership team thinks about things maybe a bit more tops-down in a sense of like, hey, these are the big areas that we know we want to make progress on. And this is kind of why we think that. I think where you can then augment that thinking is, hey, these are some of the bottoms-up themes that we're seeing in how we work day to day.

28:54And those should either validate some of the concepts or ideas that have come more tops down, or they might identify gaps in the plan as far as like, we are seeing pain in this part of our broader marketing approach. How do we want to build solutions into our plan to address those? And so I would recommend that the ICs that are out there that want to get involved and want to help. Can you, for your area of the business that you own and drive, what are some of the insights and takeaways that you're seeing in your day-to-day? And then taking those inputs and laddering it up into an opinionated point of view around what the team should be doing.

29:41Because I do think that it's important people remember, strategy is a set of integrated choices that requires trade-offs. And so therefore, you need to be opinionated around, we're going to do this and we're not going to do this. And I think that's where I see that a lot of benefit is they're closer to some of the day-to-day insights. And they can be really, really impactful if they're able to ladder those insights into these opinionated takeaways and being really clear around, hey, this is where I think we should invest. and this is where I think we should not invest. Because I think a lot of times where teams struggle is saying no to doing something.

30:25In the end, they want to do everything, but you end up peanut buttering all the work and you don't see the impact. And so I would really lean on the team that's closest to what's going on day-to-day to provide some of that color and that insights around what we should not be doing to make sure that's really clear. And then providing, making sure they're bubbling up these opportunities where, hey, there's a chance to double down based upon the data that I'm seeing in my scope or in my role. Yeah, I think that's great. I mean, a couple of things that I did to do this and based on what you're saying too is one is like, how could I do something that helps my boss hit their goal easily?