The Art of Marketing Leadership: Emily Singer

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Mark Evans: Hi. I'm Mark Evans, and you're listening to Marketing Spark. Senior marketing leaders face many challenges in today's rapidly evolving business landscape. From balancing the pressure of delivering immediate results and maintaining a robust brand identity in a competitive market, the role of a marketing leader has never been more complex and demanding. One of the topics that I'm curious about is the relationship between marketing leaders and the senior management team, particularly the CEO. When the business landscape is challenging, I suspect the strength of the CEO marketing and the relationship is also challenging. For more insight into this and other marketing topics, I'm excited to have Emily Singer, VP and head of marketing at Drift on Marketing Spark. Welcome to the show.

Emily Singer: Thanks, Mark. Great to be here.

Mark Evans: Why don't we start by sharing your journey to becoming the VP and head of marketing at Drift? It's a role that you've had since September, but you've been at Drift for about three years. Right?

Emily Singer: Yes. About two and a half years now. And I joined Drift originally to lead and build out their communications and branding organization that involve that evolved as the company continued to develop and shift strategies into a a more comprehensive corporate marketing and customer marketing role. And then, yes, more recently, back in September, our CEO asked me to step into the vice president marketing role to lead the entire marketing team, which has been very exciting and humbling.

Mark Evans: Before we talk about your relationship with the senior management team, can you talk about the job that you had as the communications branding person trying to lead? Maybe I don't know if you were reinventing the Drift story or helping it evolve. How much of a challenge was that, and what were some of the key things to being successful in that engagement?

Emily Singer: One of the evolutions that even in my first interview with David Cancel, who was our one of our founders before I joined the company, was really the need to evolve and mature the Drift story as we were continuing to move upmarket into the enterprise. So Drift built, as you know, this incredibly scrappy in at sometimes controversial outspoken brand to really break into and invent the conversational marketing space. But the product offerings and the strategy continued to develop to become more mature, and we were penetrating more enterprise customers. And so the brand needed to evolve and the messaging needed to evolve to really address those customers as we continue to move upmarket. So that was a lot of the charter joining Drift and building out the communications and brand organization to align with that strategy.

Mark Evans: Now in your experience, I I'm really interested in how the dynamic between you as the head of marketing and the CEO has evolved, especially in at a time when market conditions are volatile. I've often heard about CMOs and marketing leaders seeking partnerships with the CEO and increasingly the CFO. Discuss your relationship with Scott Ernst, Drift's CEO, and Tim Redfern, Drift's CFO and COO.

Emily Singer: The relationship with Scott has been incredibly, collaborative and successful in really partnering on the new Drift strategy, the new Drift messaging that we rolled out back in October, and collaborating on how we wanted to evolve, not just the marketing organization, but the entire company. Scott has given all of us as the leadership team a charter of really acting what we call as team one, similar to what you would talk about in a parent child relationship where the parents need to be very united and treat each other with mutual respect and alignment in order to foster the outcomes that they wanna see in their children. While not directly applicable in a familial sense, he's really brought our entire leadership team together to take on this team one mindset of aligning and adopting all of what we call our strategic growth initiatives, which are our five primary initiatives to lead the entire strategy for the year of really owning and taking extreme ownership, one of our leadership principles across every function and not trading them as marketing owns the go to market, one with sales, product owns the product initiative, but that we all have buy in and collaboration on how that works. And so he's really set the foundation for that. And then our relationship has developed from being his communications adviser into leaning in to lead all of marketing and the evolution of what that has looked like. And then Tim, more recently joining us as CFO and now chief operating officer, has also been a key stakeholder for me and my team.

Mark Evans: A couple of avenues to go down. One, conceptually, team one sounds good. It sounds like a a good business leadership concept. But practically and tactically, how does that happen in terms of building that relationship, maintaining great lines of communication, making sure that both parties are on the same page. What does the day to day look like, in terms of making sure that dynamic is collaborative and at the same time challenging each other strategically and tactically? Can you talk about how that relationship is established and how you keep it going?

Emily Singer: I'll answer it in two different ways. One more tactically, the idea of team one was explored and discussed as recently as November in an off-site that we had just North Of Boston where we came together as a more newly formed leadership team to really discuss how we wanted to operate as a team, what we wanted to hold ourselves accountable to, and the guiding principles for how we would lead the business. And so there was joint commitment as we exited that leadership off-site to acting and adopting that team one, mindset. And what that looks like in practicality on a day to day and week to week basis will lead me to the second way that I'll answer the question, and that is the regular touch points of the points of collaboration be outside of our functional leadership areas. So every other week, we have a two hour leadership meeting together where we look at tier one, tier two, and tier three metrics across the business and share where things are going well, where they're not going well, challenges that we're facing, and then have very collaborative discussions on how we can solve challenges or how we can do more of the things that are working. And one of the guiding principles that we also aligned on was embracing those critical conversations and embracing productive conflict of being willing to go to the mat and disagree and commit when necessary and really have those open conversations within a safe space of our leadership team to then go out to the market, out to the team, whatever those audiences may be out to the board, completely aligned on what that strategy, is going to look like and what we need to go do. And then the second way that I'll answer that question related to more of the tactical application is, you know, I'm a communications leader by background and trade. I think internal communications is often one of the most undervalued levers to use within an organization, and that is so critical for me as a marketing leader, but also for us as a leadership team to have those regular touch points and one on ones across all of the functional leaders to get really aligned on what we're sharing with our teams and when to cascade the most important points that need to get down to our frontline managers, to the individual contributors that make up our team. And we really on the side of overcommunicating what our teams are focused on and what we're doing next.

Mark Evans: From the outside looking in, a lot of marketing decisions these days are made by committee. Obviously, in many organizations, the CEO is the final decision maker. But increasingly, the way that I've heard things is that the CFO plays a very big role in marketing decisions, particularly around ROI, bang for the buck, making sure that capital is spent as efficiently as possible. Is that something you've seen change during your tenure as a marketing leader? And is that something that's front and center at Drift as the company tries to make sure that everything it does from a marketing perspective and, obviously, other parts of the business is as efficient and drives maximum ROI? What interactions would you have with your CFO in terms of making marketing decisions?

Emily Singer: We've all seen that naturally shift with the macroeconomic conditions that we've faced in the last year, and Drift has certainly not been immune to that. And I know you connected with Andrew, our former CRO, about this time last year talking about how 2023 would be the year of measurement. And that has certainly carried its way into 2024. And so having that alignment with Tim as our CFO to both really prioritize how we're making data decisions, data driven decisions as a marketing team. So, naturally, we're having the conversations around where that marketing spend is going to be allocated as we look at what we'll call fiscal year 2025, which starts in February for us. So we're really in the in the trenches as we speak on designing that marketing budget and having conversations of where we're making our investments. But where Scott has really been a strong leader and partner in this to elaborate on the connection with the CEO, but also in how we work with the CFO, is ensuring that those conversations between me and Tim or Tim and anyone else in the business is not happening in a silo. So how we're thinking about structuring our our marketing ROI, our marketing budget, we're really looking at that through the lens of the entire organization and what we need to go next go do next year. And a very specific example of that is we have a quickly evolving product road map and strategy that will continue to evolve and roll out into next year. And so market aligning our marketing programs, campaigns, and strategy all around at from a thought leadership level, providing the air cover on market education and what that's going to look like, aligning campaigns with the same messaging that we're sharing as far as the product evolution as AI continues to impact our business and everyone else's and what that looks like. So, naturally, to circle back to the original statement, I've definitely seen more CFO involvement as we get maniacal about how we're using more limited resources for maximum output, But I do think that's beyond just the CFO and the marketing team's responsibility and really goes back to that cross functional senior leadership alignment.

Mark Evans: I wanted to circle back on your comment about having tough conversations and the ability to have them in a safe environment. Like a sports team, everyone's happy when an organization is doing well, but it's a different story when things don't go as well as expected. Just curious about how you and Drift senior management team deal with marketing that doesn't perform. These are always tough conversations because marketing comes in with high expectations, and they're optimistic about their campaigns and everything they're gonna do. But some things are in your control and some things aren't. So what happens when a strategic initiative doesn't go as well as expected or campaigns fail to resonate? What do those discussions look like, and what happens in terms of trying to get things back on track or doing something completely different?

Emily Singer: As far as when those conversations happen, I would address that first because I think that's a key piece back to my communications comment on having those conversations before it actually happens. So as we do get more detailed and focused on where marketing ROI is and how we're seeing that realized in the output of our work. We're having those conversations on a daily, weekly, monthly basis in those leadership touch points so that we can predict to the best of our ability with the data that we have where things are going well and where they aren't so that we can come together to hopefully remove whatever those obstacles are. But us, like any other marketing team and any other business, have certainly had failures or things that we've tried that haven't worked and then coming back to why that didn't work. And the why, I think, is really the critical piece of that is really understanding, was it the seasonality? Was it the messaging? Was it the actual offer? Whatever that may be and really digging into the why so that we can make the best plan forward. And we were back to operating on principles that we've all aligned to. We focus on attacking the problem and not attacking each other. We try to assume good intent, and there are large challenges that that marketing teams are all trying to solve. A more tactical example is marketing pipeline attribution to expansion or how adoption, retention, and expansion all need to work together and at what points is our marketing influencing that when we're partnering with the customer team and how we account for that and how we pull levers together to ensure that we're retaining our customers and helping them get the most out of the Drift platform together. And there's no easy answer for that. So we've all come from different perspectives from a product led growth perspective on the product team, from the customer perspective on what they need to deliver those outcomes for customers from a marketing perspective of what's possible to be measured. And so some of those conversations are, you know, ongoing that we don't have a perfect solution for yet, but really leaning into what that challenge is and taking a collaborative extreme ownership approach to it.

Mark Evans: Sounds like a mature, if I can use that word, approach to marketing performance. But one of the realities is that there's a lot of pressure on senior marketing leaders to perform, and increasingly, a lot of them don't last very long. If you look at, some of the recent surveys, average Fortune 500 CMO last four point two years, and that's increasingly declining. What do you think why do you think that happens? Why do you think that marketing leaders have such short tenures? Is it that dynamic between the CEO and the CMO? Is it the way that companies approach success and failure? Is it simply the way of the world in terms of marketing leaders come and go? How do you explain that? And as important, what's your advice, and what's your personal view on making sure that you stay in the seat as long as possible?

Emily Singer: That is a loaded question, I would say. Where I've seen my own marketing leaders and turnover happen is usually from lack of alignment with the sales team more than anything and then ultimately the CEO. That's my personal experience and observation of where that's happened. As far as, why that is, I think I'd be remiss to also bring up that marketing is an area of business executive roles that women occupy more frequently than men. And I do think that there is some element of that, but that could be a whole other wormhole there. So I'll leave that where it lays. I think between that and then getting, like, really clear alignment on how you approach business results, I keep repeating the same sentiment. But on on the note of communication and on the note of extreme ownership together, our sales leader, Lee, and I tell both of our teams that these are owned and shared metrics. We do not break down pipeline currently by attribution. We were spending way too much time in the last fiscal year trying to assign credit, for lack of a better word, to where sales was contributing, where marketing was contributing. That's not the world that we're in right now, and we need to focus on ultimately bookings and how that's gonna influence AR together and think about all of the metrics that lead to that point. And so it's working together to ensure that we have the pipeline coverage to get us ultimately to those top line goals and focusing less on credit and attribution and more on what's working and how we're working together. Because I think anyone that's been in a sales and marketing seat understands that that line is not always clear. It may be the sales team that's initiating it and but sharing key marketing assets that helped with the education that led to that sale. It may be marketing that initially invited someone to attend a field event, but it's ultimately that salesperson that did all of the legwork to close that deal. And we see cases and cases of that. So we really take the approach of the one pipeline, one team.

Mark Evans: In many organizations, marketing and sales and sales as marketing, the lines are completely blurred. I do wanna take a step back and get a little more color on the comment that you made that a lot of CMOs don't last very long because there's a misalignment between marketing and sales. What do you mean by that? What does that look like in the wild?

Emily Singer: As an easy example in my career and observation was at a time of COVID and when that was shifting the land the landscape in an unexpected way. And we saw a a quarter in my former company, a quarter where performance did dip as we were all responding to a current pandemic and the pointing of fingers in that state of what marketing could or could not contribute when sales performance fell. And then I won't comment on the semantics of how those interpersonal relationships happen. But when you're in a state, it's easy when things are going well or even when things are going okay. But in times of crisis or in times of the unknown or uncertainty, you have to have that underlying trust that's there to be able to weather that storm. And so I think it's when you don't have that trust even in the times where things are going well or okay, then when things do start to break down, that's identified and ultimately leads to a a change there.

Mark Evans: Also wanna pick up on your comment about attribution. One of the realities of the marketing mix is that attribution is increasingly difficult, if not impossible, these days, and that some marketing activity can be quantified and some can't. There are things that don't have to be quantified because it's just part of the marketing mix, it lays the foundation for good marketing and sales and thumb some things that you do wanna lean into data, and you do wanna quantify and see if what the impact of that is. Within the Drift world and and marketing in general, what's that balancing act between qualitative and quantitative? And how do you build a marketing package or a marketing engine that that embraces both and allows different types of activities to happen in different ways.

Emily Singer: We would all love to have a silver silver bullet on exactly how that that works, and you're absolutely right. There is a balancing act and a dance on how you do that. And I would come back to my earlier comment on really thinking about the marketing investments and attribution and alignment of our goals and how we're going to measure up against the broader backdrop of what is our goal and strategy as a company. I mentioned earlier the evolution of our product road map and focusing on the key product launches that we have coming up this year and providing that air cover on thought leadership. Some of the things we'll be launching this year are disrupting ourselves, disrupting what the conversational marketing category looks like. And we, as our own marketing organization, as we primarily sell to marketers, have to evolve ourselves and shift in this new new version and react react and hopefully lead through this AI change that we're all seeing. But to get back to your specific question, that needs to inform how we make those decisions. So as an example, I mentioned you talked to Andrew about a year ago around the same time, and he was absolutely spot on that we decreased investments in a lot of in a lot of brand events, etcetera, that are less dollar in, dollar out. And that happened in 2023. Our strategy heading into the next year without getting into the specifics of it, at a macro level, we're looking at about a 25% brand spend and a 75% demand spend as our breakdown. And that 25% brand spend is going to require additional communication, additional education on how those programs are paying off. We need to go tell the story in the market about how marketing is going to change when ABM is no longer the gold standard of personalization, possibly segmentation goes away as all of this automation and the playbooks that were that we originally built as part of best practices with conversational marketing are now becoming bionic and what that looks like for personalization. So really bringing the market and our key audiences along on that journey is gonna require the air cover that is not just selling Drift or high ROI programs of dollar in, dollar out. And I frequently use, Simon Sinek's analogy of going to the gym and then lifting up your shirt and expecting to see abs on one day. Brand is very much like that. You have to commit to the long term repetitive consistency. And so being able to communicate that effectively internally and get the buy in from my fellow senior leaders. That is important, and this is how it's gonna pay off. And then also offer more quantifiable, back to your question about the CFO, outputs of that. Are our EAs increasing? Is our organic site traffic increasing? What is Google Analytics telling us as just simple examples of more of that top of funnel indicators that tell us that the brand awareness, air cover, and thought leadership is paying off for us?

Mark Evans: It's interesting that brand and brand strategy may have been top not top of mind for a lot of companies in 2023. The focus, maybe the obsession was with leads and sales. And I think one of the challenges you mentioned is quantifying the impact of of brand and brand investments can be, difficult. Do you think that as a marketing leader that it's hard to educate other people because they just don't have the knowledge and the insight into brand strategy, or is it that they're more focused on the direct correlation between if I spend x, y is gonna happen, or is it maybe a lack of patience when it comes to brand building? You know, what do you see as the biggest challenges when you're trying to wave the flag for brand strategy inside any organization?

Emily Singer: The simple answer is absolutely the measurement piece. I think it's a combination as far as what the what you asked whether it's the education piece or the being able to the being able to measure. When there's either lack of education or just lack of buy in, it always comes back to the measurement of how do we know that is working, and that is the largest challenge of being able to do that. I have had the fortune in this role at Drift having joined the company when David Cancel was still our CEO and then transitioning to Scott's leadership of having both very supportive CEOs that understand marketing and also have seen the value of branding in the business performance. So I would say I'm further up that hill pushing the boulder than other marketing leaders are perhaps, but that's also critical to have alignment not just with the CEO, but across the entire team and be able to communicate and demonstrate qualitatively through things like customer feedback rather than quantitative feedback when that when those exact attributable dollar in, dollar out metrics aren't available.

Mark Evans: You've touched upon AI throughout the conversation, and it would be remiss if I didn't ask you about AI within your world. According to Drift's, third annual state of marketing AI report with the Marketing AI Institute, 32% of marketers and business leaders survey said that their CMOs either partially or fully own AI at their organization. So what is your relationship with AI, and what's been the journey so far to integrate AI into how your team does marketing strategically and tactically?

Emily Singer: I will address the journey piece of it first. Drift has really been a pioneer in conversational AI and AI in the marketing space for much longer than many of the vendors in today's time want to claim. We have the benefit from a product strategy of really having that integrated already into our product, and that's only gonna continue to evolve. And as far as the marketing team is concerned and leadership in driving that AI transformation within Drift, but also externally, really brings together two two things for me. One is actually using our own platform. So we call ourselves org one, which just refers to Drift on Drift. We feel very strongly about being authentic and practicing what we preach, so using the Drift buyer engagement platform to see the outcomes that we preach to our customers. And that means adopting these new products like Vionic chatbots that are, as I mentioned earlier, disrupting ourselves. If we have hundreds of playbooks built that have been built since Drift's inception, and now we're moving to a strategy of how do we narrow that down to one playbook, zero playbooks, if they're all becoming bionic and shifting into that that really personalized approach using our own platform and practicing what we preach. And then equally, looking at ourselves internally, Scott attended one of my monthly I'm sorry, weekly marketing huddles with the entire team, and we didn't ask me anything with him. And somebody on my team asked him specifically, can you tell us candidly one thing that you think marketing could be doing better or is an opportunity for us in the business? And his response to that was marketing has already been adopting AI in the form of our platform. We also use tools, like, with our partners with Jasper, ChatGPT, etcetera, within our own within our own organizations. But he has really asked us and challenged us to based on those report findings of the CMO and CEO really driving this transformation to asking the entire marketing team to take more of a leadership role in the organization of demonstrating what that looks like. Can we come back to our all hands meetings and share out the results that we're seeing, the best AI tools that we're incorporating, and how we're working with those alongside with our own platform to really adopt AI internally.

Mark Evans: A lot of organizations would be interested in your take on the best AI tools out there. As to you, some challenging questions, some tough questions. Let me ask you a different type of question. When you look into your crystal ball, what do you see as some of the key marketing trends in 2024, and how is Drift's marketing approach different from last year?

Emily Singer: As far as the trend piece of it goes, I I'll start on the same topic that we're on, and that really is that I think CMOs have the CMOs and marketing leaders and marketing teams in general have the opportunity to be the change agents within their own organizations as far as AI is concerned. We've seen the stat, I think, from Gartner of the 70 of a buyer's decision and research has already been done by the time they're engaging with a brand. And so that leaves only 30% of the interactions with sales. So marketing and that number is only continuing to grow. So marketing is increasingly owning more of the buyer journey, and so that means we have the opportunity to really influence what that's going to look like and leverage AI in the transformation of marketing. That'll take me to additional predictions. I I were foreseeing things like account based marketing starting to become not the gold standard of personalization as these AI capabilities emerge. We're really talking to our customers and in our own Drift deployment of one to one personalization and understanding what that individual buyer, not the account or the company, what they actually need at that one to one level and being able to deliver that. And we've seen Drift was founded on the premise of seeing the convergence of b to c and b to b buyer expectations come closer and closer together. That has only continued, but we know from Merkel data and other sources that largely vendors have continued to not meet buyer expectations. And our take on that is it's because of the lack of scale when you don't have human capital to address every single one of your customers, every single one of your prospects on a one to one level. Now we're seeing AI step in and actually make that possible. And so we need to anticipate both from a product strategy, but also as an our own enterprise company, how to anticipate that shift in marketing and what that's gonna look like.

Mark Evans: Final question. Where can people learn more about you? And Drift is obvious, but where can they learn more about you?

Emily Singer: Learning more about me specifically, I would LinkedIn would be the best resource for that, or I have the same handle on every social media, e m c c singer, which I believe is also my LinkedIn. And, yes, Drift, is more obvious, but drift.com. And I would say the most exciting thing to check out right now is our Bionic chatbot demo where you can type in your own company website and see what I'm talking about of how this is gonna shift marketing and building Bionic playbooks for yourself.

Mark Evans: Thanks, Emily, for the great insight into all things marketing, including that interesting relationship between the head of marketing and the senior management team. And thanks to everybody for listening to another episode of Marketing Spark. If you enjoyed the conversation, rate it and subscribe via Apple Podcast, Spotify, or your favorite podcast app, and share via social media. If you're a b to b or a SaaS company looking for more sales and leads but struggling to do marketing that makes an impact, we should talk. I work as a fractional CMO and strategic adviser. My services included a ninety day marketing sprint that combines strategy and tactical execution to move the needle quickly. You can reach out to me via email, mark@markEvans.ca, or connect with me on LinkedIn. I'll talk to you soon.