Ep. 574 - FAN FAVORITE | Mailchimp former Chief Operation Officer Sheldon Cummings – Watch How Resilient Leaders Win BIG Inside Corporate Giants

Summary

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Episode Overview

Title: FAN FAVORITE | Mailchimp former Chief Operation Officer Sheldon Cummings – Watch How Resilient Leaders Win BIG Inside Corporate Giants
Host: Cameron Herold
Guest: Sheldon Cummings, former COO of Mailchimp
Release Date: April 28, 2026
Theme:
This episode features Sheldon Cummings, who shares the trajectory and leadership insights that led him from consumer packaged goods (CPG) industries to top-tier roles in tech and, ultimately, to serving as COO of Mailchimp amid its acquisition by Intuit. The conversation weaves through his background, how large organizations can remain agile, strategies for melding company cultures, and the keys to resilient, connected leadership—especially during periods of change and uncertainty.

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Key Discussion Points & Insights

1. Building a Career: Prioritizing Opportunity and Adaptability

• Early influences:

  • Grew up in New York City; program for inner city youth (Albert G. Oliver Program) placed him in a prestigious prep school, which broadened his horizons and fostered “prioritizing opportunity” regardless of location.

    “As I've been looking at building my career... it’s been very focused on what’s the opportunity, wherever the location might be.”
    —Sheldon Cummings [06:10]

• Career journey:

  • Diverse experiences in both the U.S. and Europe, including senior leadership roles at CPG giants (Kimberly Clark, Kraft/Mondelez) and Intuit.
  • Strategic “toolkit-building”—actively embracing roles outside comfort zones to maximize growth and learning.

2. Lessons from CPG to Tech: General Management and Data Storytelling

• GM foundation:

  • Early general management program at McMaster Carr: exposure to multiple business functions (marketing, accounting, warehouse, sales) at a young age.

    “At a very young age, having some level of supervisory kind of experience... that cross-functional nature is critical.”
    —Sheldon Cummings [07:41]

• Consumer and data obsession:

  • Translating consumer focus from CPG to tech by always keeping the end-user at the core of business strategy.
  • Ability to synthesize data across departments and tell a compelling narrative.

    “One thing that you learn is how to decipher and tell a narrative from numbers... you had to... pull a story and say, ‘what do we do next?’”
    —Sheldon Cummings [13:48]

• Cross-functional collaboration:

  • Emphasis on “win-win-win” outcomes when partnering with others—benefits for the company, partners, and end customer.
  • End-to-end thinking: the whole customer funnel from acquisition to retention [24:21].

3. Navigating Corporate Acquisitions and Culture

Mailchimp + Intuit: Integration & Impact

• Mailchimp’s role:

  • Leading platform for email marketing and automation, helping millions of small businesses worldwide grow.
  • Acquisition by Intuit designed to couple Mailchimp’s growth/enablement tools with Intuit’s backend solutions (accounting, payroll, etc.).

    “It’s this virtuous cycle of both the growth, growing one’s business and running one’s business and how they work and interact together.”
    —Sheldon Cummings [21:10]

• Cultural bridging:

  • Challenges of integrating two organizations, especially during COVID when relationships were formed virtually.
  • Emphasis on constant communication, transparency, and rapidly building new “connective tissue” across teams.

4. Product Management: Ruthless Prioritization & Sunsetting

• Staying lean:

  • Importance of a disciplined product roadmap guided by robust customer insight—not simply building features on demand.

    “If you’re just constantly running and just launching things... your customer is going to get flooded... it becomes dilutive versus accretive.”
    —Sheldon Cummings [22:31]

• Feature “sunsetting”:

  • Actively identifying features that need to be retired to avoid clutter and confusion.
  • Ongoing testing and iteration processes to ensure feature viability before full rollout [27:26].

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Leadership, Resilience, and Development

1. Leading Teams Through Change

• First 90 days as COO:

  • Focus on vulnerability and humility—being clear about what’s not known, asking questions, and striving to be a “learn-it-all” (vs. a know-it-all).
  • Ensuring alignment in mission and values between Mailchimp and Intuit.

    “People know... if someone’s coming in thinking they know everything. I try to be more of a learn it all than know it all.”
    —Sheldon Cummings [31:44]

• Mid-level manager development:

  • Teaching leaders the art of leading through uncertainty, embracing change, and accelerating team growth.
  • Feedback loops: regular employee engagement surveys; making actionable changes in response to feedback.

    “That notion of leading through change I think is one that we are continuing to work with and reinforce...”
    —Sheldon Cummings [34:23]

2. Personal Professional Growth

• Maintaining the “bridge” between organizations:
  • Leveraging strengths of both Mailchimp and Intuit to accelerate business objectives.
• Community and connection:
  • Post-pandemic, prioritizing in-office moments of connection, informal collaboration (“hallway conversations”), and fostering community.

    “There is power that comes from those hallway conversations... I’m trying to continue to build that sense of community.”
    —Sheldon Cummings [38:27]

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Notable Quotes & Memorable Moments

• On resilience and comfort zones:

  “The benefit that is immediate... is this notion of resiliency, this notion of putting yourself into environments where you’re not comfortable and sort of relying on yourself and quickly building a network and quickly building trust.”
  —Sheldon Cummings [09:17]

• On scaling product organizations:

  “Understanding what you sunset is important too... you want to prevent as much as you can that long tail, which could be confusing to customers and sort of muddy down the experience.”
  —Sheldon Cummings [27:26]

• Advice to his younger self:

  “Pick your head up from time to time and—what else can you absorb? ...Are you truly getting as much as possible from... the various people that you’re bumping up sort of against? Are you maintaining those connections, relationships over time?”
  —Sheldon Cummings [39:20]

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Timestamps for Key Segments

• 02:00–08:00 — Sheldon’s background, early education, international experience, building a career toolkit
• 11:40–13:40 — Lessons from Switzerland, importing user experience and efficiency into business practices
• 13:38–16:23 — Lessons from CPG: narrative from numbers, consumer obsession, and cross-functional work
• 16:37–19:38 — Mailchimp’s business model, impact of acquisition, leading a global organization
• 22:13–23:46 — Product roadmap discipline; keeping features focused
• 24:21–27:26 — Data selection at scale, instrumenting user journeys, feature sunsetting
• 31:44–34:23 — Leading post-merger, building trust as a new executive, aligning missions
• 34:23–36:47 — Training and elevating mid-level management through change
• 36:51–39:04 — Personal leadership development, community building post-pandemic
• 39:16–40:20 — Advice to young leaders and reflections on career priorities

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In Summary

Sheldon Cummings’ journey from New York’s public schools to the C-suite at Mailchimp is a masterclass in seeking and shaping opportunity, shepherding teams through uncertainty, and building lasting impact inside complex organizations. His emphasis on humility, data-driven storytelling, and staying genuinely customer-obsessed offers actionable wisdom for Second in Commands and aspiring leaders alike. The episode is peppered with stories of resilience, lessons in cross-functional leadership, and strategies for maintaining connection—reminding listeners that scalable success depends just as much on human relationships as it does on strategy and systems.

Transcript

[Cameron Herold]

Hey there. Just a quick note before we dive in. This is actually one of our older episodes, but we're bringing it back because it's one of the most downloaded ones we've ever released. Clearly it struck a chord with a lot of listeners and I know there's so much value packed inside. So whether you're hearing it for the first time or revisiting it, enjoy this fan favorite.

[Podcast Announcer]

Welcome to the Second in Command podcast produced by the COO alliance and brought to you by its founder, Cameron Herold. In the Second in Command podcast, we Talk to top COOs who share the insights, strategies and tactics that made him the Chief behind the Chief. And now, here's your host, Cameron Herold.

[Cameron Herold]

Our guest today is mailchimp's Chief Operating Officer, Sheldon Cummings. Before stepping into his leadership role at mailchimp, Sheldon had a dual role as vp, Intuit Sales, in addition to serving as Intuit's Chief Diversity, Equity and Inclusion Officer. Since Joining Intuit in 2017, Sheldon has led a number of leadership division or positions across Intuit's sales, marketing, global partnerships and global operations teams. Prior to Intuit, Sheldon had a number of roles across industries and countries, including leading a European business for six years. Headquartered in Zurich, Switzerland. Sheldon, a native of New York City, graduated with a BA from Wesleyan University and received his MBA from Northwestern University's Kellogg School of Management with concentrations in finance, marketing and strategy. Sheldon, welcome to the MCRAN podcast.

[Sheldon Cummings]

Thank you so much, Cameron. Great to be here.

[Cameron Herold]

Yeah, you are one of the smart guys.

[Sheldon Cummings]

If only. If only. If only.

[Cameron Herold]

Yeah. Kellogg is not exactly a C level school. That's a pretty solid, solid school to get through. I've got a lot I want to dive into, so I want to find out kind of how you got here. I want to talk to you a little bit about Zurich, Switzerland. I want to talk to you about, you know, what it was like kind of working with mailchimp inside of a bigger organization. So we'll kind of let the conversation happen organically. But why don't you give us a little bit of your background and what got you into your role today.

[Sheldon Cummings]

So as you mentioned, I'm native of New York City, so born and raised in Cyprus, Brooklyn. My family now lives in Queens. And when I was growing up in New York, there was a program called the Albert G. Oliver program. And I'm going to go way back because I think it all building blocks, right? And so this Albert Galliver program, which took kids within the inner city public schools and sort of gave them opportunity, exposure to prep Schools. And so I didn't even know what that was growing up, you know, in New York. And I had an opportunity to go to a school called George School, which was in a Quaker school in Pennsylvania for high school, and sort of was one of those first building blocks, if you will, for prioritizing opportunity. And, you know, my mother is from an immigrant from Trinidad. My dad's from New York City. And I think, well, what's. What's true in my household is a focus on education and a focus on opportunity. And so went to high school, Pennsylvania, as I mentioned, then went on to Wesley University in Connecticut, as you talked about, and there again, focused on how I was building that toolkit, then moved on to Chicago. So I worked at a company that had a general management track called the mastercar. And I like to equate that to kind of like a Home Depot for businesses, if you will, small manufacturing firms and. And worked there for a number of years. Got my MBA when I was in Chicago, and then moved on to my CPG career, consumer package goods. And why I picked that path was it was a path where you had increasing levels of responsibility, but very much around that general management lens, that, that combination between, you know, sort of strategy and finance and marketing and how they came together around the consumer and that consumer insight. So moved to Kimberly Clark, worked on the Huggies business in Neenah, Wisconsin, for those that might know the northern Wisconsin area. So was in. Was in Neenah and then moved on to Kraut Foods in New York. Had a variety of different roles there through bigger and bigger pieces of the portfolio. So my. My last role in the US Was managing the Ritz Cracker business. So go Big Red. And I really wanted an international experience, and I wanted international experience that was from outside of the US Lens. I think many, many people typically, you know, manage global businesses, but I wanted to do so in a different context where I can see and run an international business from an international location. So that took me over to Zurich, Switzerland, where Kraft Foods, or what became Mondelez at that time was headquartered. And I had teams on the ground in a variety of different countries, you know, within Germany, Switzerland, et cetera, sorry, Austria, Sweden, et cetera. And basically was. Had a Portfol from a general manager perspective. So even though I was there for six years, my Deutsche niche are good. My German is not very good, even for being there that long. But I pivoted at one point and said, okay, do I want to become European or do I want my kids to grow up sort of in the states, near family and grandparents, et cetera, and made the move to tech and moved to it in California back in 2017. What's interesting is people might think that the chasm between packaged goods and sort of tech is a large space. I think often within consumer tech, you're obviously engaged with consumers all the time. And so that's TurboTax. If we think about people who are doing their taxes every day, and even with many of the small businesses, often they are consumers. They're very small business, smallest businesses. They're consumers with a skill. Right. They have a skill set, they have a dream, they have a passion. And that was a relatively smooth transition. So moved over to Intuit, had a variety of roles within that time. I can talk to you more about the diversity, equity, inclusion, lead role before I moved over to CEO because that was also an interesting sort of building block. And then became the chief operating officer at Mailchimp Quality Acquisition back in 2021.

[Cameron Herold]

Okay, so you just gave me a whole bunch. And it's funny that you almost answered all a bunch of my questions as you were even talking too, when you said that, you know, the leap from. From these bigger brands into. Into tech, I was like, it seemed like going from. It seemed like oil and water to me. Right. It seemed like. So I don't know where to go. Where to go here. I got a whole bunch of spots. Let's go back to the. You said something about prioritizing opportunity at the Quaker school. What did you mean by that?

[Sheldon Cummings]

Yeah, great question. So I think often you either are really focused on as you're building a career, you're potentially going to be geolocated. Right. And so saying I'll take whatever the opportunities are that might happen within a certain location, or you might be focused on the opportunity, wherever the location might be. And so as I've been looking at building my career and my education, it's been very focused on what's the opportunity, wherever the location might be. So that's what took me from New York to Pennsylvania, Connecticut, Chicago, Switzerland, California, and then now Atlanta, Georgia. So all those things is when I really looked at kind of prioritizing where that opportunity was and how that could help sort of build that toolkit.

[Cameron Herold]

Build that toolkit off. What do you think? Some of. And you mentioned this, the GM truck that you were in and was it. Did you call it Mastercar?

[Sheldon Cummings]

Oh, so there was. The company was called McMaster Car. Oh, so yeah, it's a pro. Yeah. And most people say. Do you say MasterCard? If you are in the manufacturing space and you look for a solution of a catalog that has anything and everything in it. That's the company. And they had a general management program where you spent time, this is right out of undergrad, where you spent time in, in marketing and accounting and the warehouse and sales. And so it was a great foundation before then I went on to B school and then went on to package goods.

[Cameron Herold]

That's amazing. That was what I was curious about was what was that GM track. So it was really giving you the exposure to all these different business areas.

[Sheldon Cummings]

Correct. And then at a very young age, having some level of supervisory kind of experience and that component of how important the people are, whether you're leading and managing individuals is key. And that cross functional nature is critical. Right. So all my years that I spent in Crowd Foods and Mondelez, I don't know how to make an Oreo, you know, I can't make a ritual cracker to save my life. But it's how you work with the teams, with the consumer always at the center. Right. Building the innovation to bring forward.

[Cameron Herold]

It's interesting, Starbucks at their head office level does that with their management as well. They move their management around often every two or three years. They kind of take you out of a role and they move you on purpose to give you more exposure to kind of create that, that real top line leadership. Do you do that now within, you know, mailchimp, within Intuit or.

[Sheldon Cummings]

Yeah, I would say that there is, there is this notion of how are you building, you know, your box, right. How are you building that, that experience that. I wouldn't say that it's a structured rotational program, but it is where, you know, when we think about mobility and into more broadly, we don't think about mobility of someone's career only being, you know, up. It is also across how are you building those experiences from a variety of different lenses? Because when you have those different perspectives, you'll have an outsized impact.

[Cameron Herold]

So you've got kind of the skills from there, you've got the cross training and then you've also got. Did something happen with you at the private school as well that you saw the, the, the value of a network or, or kind of that. Did you see anything and learn anything from that that you still carry with you today?

[Sheldon Cummings]

Great, great question. The truth I would say is not immediately so. And let me break that down. So when you first get out of school, whether that be high school, whether that be undergrad and even for college, graduate school, for me it wasn't an immediate impact of the network. I think as you progress through your career, then you find connection points as you are potentially interviewing with a company. And now it's the so and so that I used to work with is also at that organization. And then you're building that connection where you can learn more about it and what really is happening at that organization. I would say the benefit that is immediate when you're going through the private school and college, et cetera, is this notion of resiliency, this notion of putting yourself into environments where you're not comfortable and sort of relying on yourself and quickly building a network and quickly building trust to then. To then navigate and have an impact. And so didn't know what that high school was, Never heard of, prep school, never lived outside, you know, overseas, you know, before in the US and when people hear about my background, they would think about me being more in a military family. But the reality is, is my. My parents are still in the same home that I was in, you know, when I was a kid.

[Cameron Herold]

I love the fact that you get to live in Switzerland too. Like, you couldn't have picked a more perfect country, Right? It's just amazing.

[Sheldon Cummings]

It's absolutely amazing. And one of the things about Switzerland, which is fascinating is just how the society works so smoothly. Like, you know, there's the stereotype and. But it's actually true.

[Cameron Herold]

It does. Like, it's crazy. They say that the trains, like, leave and leave. Exactly. They just leave on time. Like, everything works like a Swiss clock. It just functions.

[Sheldon Cummings]

It just. I'll give you one, one quick aside. So in my time there, there was. And you live in the city of Zurich, there was a little app that you would have on your phone, right? It's called the ZVV app. And with this app, you can pick any location you are in the city of Zurich and any location that you want to go to. And the app would map out the amount of time it would take to walk to the bus, the time the bus would arrive, the time the train would arrive, the time would take to walk to the final destination. And I tell you, it literally worked perfectly. Yeah, like that. So can you imagine how much from a clockwork perspective it needs to be to make that type of system work? And it did.

[Cameron Herold]

Do you ever try to bring any of that into the business?

[Sheldon Cummings]

Well, I think that what you try to bring in is that user experience in those magic moments. Right. So as we are digging into the consumer insights, our customer insights, as we're thinking about the overall experiences, it's really about how you are. One, from a UI perspective, how simple is that, how engaging is that? And then two, how do you leverage AI and all the machine learning to make it even easier to bring that magic to the hands of the, of the customer so they're not, you know, we, we want to support and continue to support that underdog. Right? We want to support that person that has that dream of the small business and they're willing to put that into action. And when you think about the importance of what small businesses know, mean, you know, in the US for example, there are a million, 61 million small businesses across. They are truly the ones that are driving a key chunk of the economy. So being a tool that not only helps them sort of with their books and obviously their taxes, Equip Works Turbo Intuo, Equip works intuit turbo sex, etc. But then also how with intuit mailchimp, we're helping you grow your business. What we do is try to bring the power of the platforms together to, to make magic for the customers and help them deliver against their dreams.

[Cameron Herold]

I love that, I love that you just gave a data point of the 64 million US small companies too. It's crazy town. Okay, I want to ask you about. Everybody tells me about, you know, their, their experiences and what they've learned out of their mb. So I'm not going to ask you about that. I've always been kind of enamored with the CPG space, the consumer packaged goods. When I was graduating from university, I really got. Wanted to go work for Proctor and Gamble and I wasn't the smart kid, so I just didn't get to do that. And I was running my own business at that time anyway, I guess. But what do you think you pulled from the CPG experience? Because for me it seemed like you were kind of running a business, you know, entrepreneurial in a way that you were kind of running a business or a business unit. But what skills did you pull from that that you carry with you today?

[Sheldon Cummings]

Great question. I like the way you just like, yeah, I was actually running a business at that time, so you.

[Cameron Herold]

I had 12 employees when I was 20 years old, so I really was.

[Sheldon Cummings]

That's awesome. One thing that she learned is how to decipher and tell a narrative from numbers. So before you ever do a commercial or mess with marketing or any of that, you need to be able to understand the fundamentals of the business. And so every week when we started out, we had to say, this is what happened last week from Nielsen, this is what happened across our, the competitive set, our share, what was happening across the overall business. And you had to, in essence, is that on plan, is it not on plan and be able to tell a narrative off of the numbers. So that was a great sort of foundation because you literally rolled up your sleeves, got into the data, but not only sort of reported the data, but had to pull a narrative, pull a story and say, what do we do next? The second key foundational component that you bring forward today is this notion of that consumer obsession or that customer obsession. When you're thinking about the brands that have been around for a long time, you say, well, how can you innovate anymore and how can you drive any more impact? But this notion of that customer and that consumer is at the heart of everything that you do and you're not able to sort of build more broadly without them is something that's true, was true within cbg. It's something that's true. Add into it today we have processes like Design for Delight, which we're actually, we actually look at how we're getting the insights for the customer that we have and how we can bring that through our products. The third one is that cross functional nature that I touched on and it's even more complex when you think about the level of functions that need to be included. So that's both the people that are doing the marketing, the people that are doing the manufacturing, the supply chain, the quality assurance, the customer. Right. So now you're bringing in another intermediary in the process and how are you going to sell and give that co benefit? And that's another thing that you can bring forward in your career is as you think about partnerships and how you're leveraging partnerships, it needs to be that win, win, win. Right. A win for the organization you work for, win for the partner and then the win for the joint customer. So that notion of how you bring that through is another, another critical piece. And then lastly, I would, the, the sort of the, the vision and setting the strategies, initiatives. How are you setting the vision for this brand and business as we move forward? And then how does that translate into the strategies and initiatives that we have and how we have accountability every single week? And so those are great foundational skills that you have and can take anywhere.

[Cameron Herold]

I love it. All right, I, I had some questions around data that I'm going to get to next, but I just realized we're, you know, 20 minutes into the episode and I haven't even asked you to tell us what mailchimp is. And how did that kind of acquisition of Intuitive mailchimp go?

[Sheldon Cummings]

So mailchimp, basically what's interesting about about us and the company is we are one that is an email marketing and automations platform. So mailchimp focuses on how we drive for that underdog and how we're looking for growing businesses. And so we're empowering millions of customers around the world to build and grow their businesses. And we are putting sort of data backed recommendations at the heart of our customers marketing. So we talked a little bit earlier about how you can leverage data information to help the end customer. And that's what we're doing sort of every day across, whether it be email or social media, the landing pages, the advertising, et cetera, and how that can be powered by the AI talked about the company is a global organization. So from a global organization perspective, half the business is in the US and half is outside. And so when you think about that mix, it's amazing and how we're able to engage customers truly around the world. The acquisition piece so from an acquisition perspective, as I mentioned earlier, Intuit is very, very strong in sort of those backend components working on people's books, their accounting, their taxes, as well as all the other necessary components of how to run payroll, Intuit payments, et cetera. So all those core building blocks running a business. But one of the pieces that customers are asking for is help me grow, how do I grow, how do I engage with my customers that are here, how do I get more revenue? And then that's where mailchimp came in. So it provides sort of both ends of the need, both how we help customers grow every day as well as how we help them run their businesses more effectively. The acquisition closed back in November of 2011. And you know, through that time what was interesting was if you take a step back, it's different today because obviously many of us have gone back to our kind of like quote unquote daily lives. But back in November, we were still very much in sort of the throes of COVID if you will. And so going through that from a engagement perspective and how you're engaging teams and how you're engaging people that you haven't met yet, but yet you've acquired through Zone was a huge learning, you know, for me. How do you keep that? How do you make sure that they know who Intuit is and understand that organization? How do you make sure that you build those bonds and connections through a screen? And so we take that for granted of how to do that and how to build those relationships. And I think that that's one of the interesting parts and unique parts about this acquisition versus typically many others. There were a number of people who started at Intuit mailchimp who never met their peers live right, much less have gone through and meeting other people within Intuit. So one of the ways that we worked through that was not only sort of the constant connection, you know, via Zoom, but then once things started opening back up, forging ways to build the connective tissue between the two organizations.

[Cameron Herold]

I love that, by the way, when we're offline, I'll, I'll send a link to you. It's about something called Workplay Jam, but it could be a fun way to build some more connections. It's these online social fun activities that groups run for you to kind of merge these hybrid teams. Well, I'll send it to you later. Hey, it's Cameron Herold, founder of the Second in Command podcast. Are you a COO who's struggling to level up? Every COO or second command should join the COO Alliance. Go check out COO alliance.com and for just the cost of a few coffees a month, you can get world class training, 12 monthly masterminds, and attend two live events a year with top COOs from around the world. For the last 10 years, we've been building and growing the CO alliance to put the tools, peer support and strategies in place to help COOs grow themselves. And their companies, backed by rave reviews from hundreds of COOs and their CEOs have seen insane growth. We also have a 10x guarantee. It's your tribe. Go check out cooalliance.com, sign up for a quick call to learn more. Welcome home. My question though, around mailchimp is was it an acquisition that was a strategic acquisition? Like, were you doing it as a way to. What, like what was the strategic part? Because it, it doesn't necessarily make sense from the outside looking in as to why Intuit would buy it. What was the, what was the strategic reasons?

[Sheldon Cummings]

Yeah, so, so from a strategic reason, that's the pillars, right? It truly is. It trul. Foundational around that growth component, right? It truly is. So I'll give you an example. So one of the things that mailchimp towers in is how that engagement component for say, emails, right? So email, email marketing and that customer relationship piece. So now as you think about leveraging that as a platform, we could do and leverage multiple tools within the Intuit, you know, sort of family for things like you know, receiving payment through that method. And then that's something that makes it easier for our end customer because they're used to both sides of the spectrum. They're used to it. They're used to how they're leveraging the email and now they're also used to how they are creating that email to have more power with things like being pay enabled and then how that then links back to the overall books and it helps them run their business better. And then they can see the effectiveness of the marketing. And so you can see how it's this virtuous cycle of both the growth, growing one's business and running one's business and how they work and interact together.

[Cameron Herold]

Chris, just on the product side of things is how do you stay lean as an organization when you have the opportunity to continue to, you know, add features? Right. When every customer has, oh, I would love it even more if it did this or, you know, we could use your software if it only did that. How do you, you know where I'm going?

[Sheldon Cummings]

Yeah, no, I know where you're going. Right. So a lot of that is about the, the product roadmap, right? So how you have the product roadmap that is again, still grounded in the insight and what our consumers and customers are saying. But that's where the discipline comes in, right? Because in essence, when you have your product roadmap and how that ties into your strategic plan and the initiatives that you're trying to bring forth for the customers, you're doing that rugged prioritization process as a team and as a cross functional team, you're understanding what the impact is of the various product launches that we have. You're aligning with everything from your marketing side. Your engineers, your product managers, your customer success component. Like they all have to be aligned and know what's happening and then that gives you that magnified impact. If, if you're just constantly running and just launching things, one, you're never going to break through the noise in terms of the communication. There's not going to be the clear awareness. Your customer is going to get flooded with a variety of different messaging and so it becomes dilutive versus accretive. So it's that, it's that rigorous prioritization and that cross functional connection that's needed in order to have the impact, the desired impact that you want.

[Cameron Herold]

I'll go back to the data for a second. You kind of mentioned earlier about, you know, you had to be able to tell the story from the data and really looking to interpret the data, it's kind of like in any organization, there's almost an infinite amount of data.

[Sheldon Cummings]

Right.

[Cameron Herold]

I guess as the organization scales, you've got every business area is all their data sets as well. How do you know at the COO level what data to look at and what data to kind of hide? Like what if I picture like a spreadsheet of a gazillion rows? How do you know which 9,000 rows to hide and which four or ten to look at?

[Sheldon Cummings]

Yeah, no, it's a great question. So my role within COO is very much focused on our go to market. So our marketing, our sales, our customer success, our care strategically, where do we go as an organization and our operations and then working, you know, sort of cross functionally with our engineering team and our product management team. And then obviously we're supported by legal, hr, et cetera. So as we're looking at that growth component, it's the end to end customer funnel for the key metrics. And so when I say the end to end the key metrics looking at is how are we doing from an acquisition perspective and are we acquiring the customers at the clip that we intend based on our media spending, et cetera? The second piece is a mailchimp is very much a product like growth organization. Right. So you can start and join sort of mailchimp for free and then work your way through the various features that we have. And so looking at that discovery and active use of our customers, how are, how are they engaging with the products and features that we have? And then how is that translating to a booking? Right. How is that translating to a paid customer? And what is the experience that they're having from that lens around? You know, again, looking at active use of features and then the retention component. Right. So how are we retaining and is it just, you know, sort of a leaky bucket or not? Those are some of the main ones that we're looking at because it gives you a lot of information from the acquisition side to the use and that is a key indicator to what the retention will look like. You have a number of other KPIs that we do look at and that we measure, but the health of the business for you to say from a snapshot perspective, holding costs relatively equal. Right. That will give you some of the most important critical metrics.

[Cameron Herold]

I'm curious, are you able to see which features or which functions of the software customers are using and which ones are just kind of laying idle?

[Sheldon Cummings]

Correct. You can see. And that instrumentation is an important point. Right. So not only the instrumentation in terms of what are people using from features, et cetera, or not. But then also looking at the funnel, right? So when people are landing, where are they hovering? Who is engaging with the sales team, who's engaging with chat, Those that are going through the rest of the funnel, where are they getting hung up? And where do we have sort of drop off that will help you optimize to have the impact that you want so that they have a smooth and easy experience.

[Cameron Herold]

I often think about, you know, something like Microsoft Excel and how many gazillion features and functions there are within that software. And there's probably like 50 that we use, right? And then there's like 5,000 that seven people use. And I always wonder why. Or do companies try to. Do you try to eliminate some of those to try to bring the product set back to something that's simpler? Or is it just. You just keep building out something and if people use it, it's there. And how does that work on the product side?

[Sheldon Cummings]

Yeah, so we definitely. So one, your point is true. There's always going to be a curve and a long tail, right? So that, that is always that true about every product that exists. Going back to your earlier point around, do just build things. Well, the goal of that ruthless prioritization and the testing is to ensure that when you build it will have that desired impact and have that use that we're looking for with our customers so that it's not just adding to that long tail. Understanding what you sunset is important too, right? So it's not just. Just what you build is also what you sunset. Now, the. The goal will be as you are doing your testing for a launch and as you're iterating, because speed is critically important of continuing to learn and test as you go. The goal would be to do as much learning as you can before you, let's say, do a full roll up. You're understanding that level of engagement with the cohorts so that you are knowing which will land the way you intend. And so that those are all the things that we put in place. One is the rigorous prioritization and testing. Two is you're testing along the way and pivoting through that journey to ensure that you have the optimal experience. So you prevent as much as you can that long tail, which could be confusing to customers and sort of muddy down the experience, but also be willing to sunset things when needed.

[Cameron Herold]

I love that. All right. Curious about when you came in as the COO for mailchimp. I mean, so there's an acquisition. How many employees were in or at Mailchimp when you joined?

[Sheldon Cummings]

Yeah, so Mailchimp, you know, roughly has 1500 plus employees. And so, you know, what we've done throughout that time is it's in that ballpark, we're a few hundred more than we were when we started. And again, we started that within, in the COVID context, we are predominantly within the US from an office location perspective. And the headquarters that we have is in Atlanta. So it's been in Atlanta for a few decades and really has a sort of unique space and presence in the Atlanta market. One of the things that's been very welcoming and different is I used to be in San Jose, as I talked about into its headquarters is in Mountain View. And there are, obviously it's Silicon Valley, it's the Bay Area that we know of. And so the number of tech companies you could, you can't count. What's great about Atlanta is not only is it a strong tech scene and a growing tech scene, but then because, you know, mailchimp has had such a presence for so long, both within the tech scene and within the community, the number of people that you connect with that you might say, hey, you know, I'm the chief operator at mailchimp. Oh, and you'll get a story, right? Or it is not just a story from a tech lens, but also the impact of the community community, because throughout that time there's been a lot of, you know, corporate, social, giving, etc. And it's been not only the tech, but also the impact on, on the, the community and organizations in Atlanta. So it's, it's, it's something that we are building on from an Intuit perspective and we're looking to continue that. I think that's one of the questions that I received, you know, when I started is, well, now that mailchimp has been acquired by Intuit, does that mean that, that we're going to be less invested in the Atlanta area? And actually it's the contrary. One of the programs that we support is Clayton State has its technology program. And what we've done since the acquisition is taken that mailchimp foundation from a funding perspective and then tripled it. So that's one of those types of examples where we're really invested in the Atlantic community.

[Cameron Herold]

I love this. So question I've got related to that was when you came in as the COO, there was, you know, 1500 ish people that were already there before you. How did you navigate that whole like, well, who the fuck is he? Like, why does he get the job that I didn't get? And now I'm reporting to this new guy. You know, at least you're likable, but, you know, it'd be hard for somebody who is a jerk. You seem like a good guy. How did you. How do you move into an organization above everybody else and build the relationship? What is the first 90 days like? Can you give us any lessons there?

[Sheldon Cummings]

A couple things. One is really starting off with being human first. I know it sounds cliche and those types of things, but. But being vulnerable with the teams and the people to say, you know, there's a lot that I don't know there's about mailchimp. There's a lot that I'm looking to learn from all of you. And there's an opportunity and excitement to work together. And people know and they can tell whether someone's coming in thinking that they know everything. And I try to be more of a learn it all than know it all. And so asking questions of the team, asking questions of the leadership, and again, doing this over zoom, not doing this in person. Right. Where it's a lot easier to. To build those connections by, by asking those questions and then. And then playing back that what we've heard then linking the overall insights that are being presented to strategies and initiatives that they see later. They see their voices in the outcomes that are driving in total three, I would say, is ensuring that they know that the missions of the organization are the same. You know, Intuit is focused on prior and prosperity around the world. Like that is truly what it's about and how we are championing the underdog. That same language is used Intuit mailchimp and has been in terms of how to champion that underdog, that focus on small businesses and the resiliency that's required in our here to help. So that's another sort of tick point where people can say, okay, I'm being heard and I can see how my voice is included in some of the direction and I understand the why. And that why is the same for both organizations. So I know that where I've invested my time for the last few years, I know that this new organization is similarly minded, similar passions and interests and outcomes that they're striving for for the customers. And so those are some of the things that we put together to win the hearts and minds, if you will, of the employees.

[Cameron Herold]

I like that. I'm not thinking of your direct reports because I would imagine your direct reports are fairly seasoned, solid executives already. I'M thinking of one layer below them. Not just say that these, this next group is not seasoned or solid, but what kind of skills are you trying to impart on that kind of mid level management group? And my question is because I launched a course recently called Invest in your leaders and I have these 12 skills. I'm curious what you're working with those kind of mid level managers. What are you trying to skill them up on the leadership side? So less about, less about your product and software, more like the skills and leadership. Where do you focus with them? Where are you trying to grow them?

[Sheldon Cummings]

Great question. So one thing that especially as you're going through change and we're all going through change at rapid paces and again, I know it sounds cliche, but it's true. Especially when you think about, about how to navigate and lead through Covid. Right. That's something that people have not seen before. And so this notion of leading through change, right. Leading at a speed and a rate through change because often the middle managers can be frozen and they are critical to the success of how messages and how key strategies get implemented across the whole organization. So their buy in and their leadership, right. It's like it's not only about kind of being on the sideline, but it's also about being there in the game with the leaders to help continue to drive and put forth, push through change. When yes, there's a lot of uncertainty, yes, there might be concern about, you know, what about me? Yes, there might be some unknowns about how we navigate this because we haven't seen it before. And so that notion of leading through change I think is one that we are continuing to work with and continuing to reinforce. The second piece is around how the teams are continuing to assess and sort of push talent on their teams because that is a key component. As we think about that acceleration component, how we accelerate that team assessment, that team development, that team leadership, that's something that's a skill like every other one, right. It's not something that just happens, it has, we have to be intentional about it. So there's a lot of foundational learning that we have within the internal structure that we have going across into the mountain to focus on, you know, development and development or managers, development of skills, those types of things. Because it's a critical piece for how we move forward. So leading through change, the development of the team and then how we cascade that information down and have that listening loop. So we do engagement surveys, you know, a few times a year because we want to know where the Employee base is right. We want to know how they're doing and then how are we going to be actionable about those insights? So it's not just listening for listening sync. It's truly about the here's what we're hearing with our various cohorts and then now how are we going to address it? The same way we would with our customers.

[Cameron Herold]

I love this. All right, how about yourself? Where are you working on your skill sets?

[Sheldon Cummings]

I'm continually working on, you know, one, how being that bridge, an effective bridge between sort of the mailchimp organization and the Intuit organization. Right. Because in essence, I know both. But how do we ensure that we are moving with speed through those both, both of those organizations? So that's one thing that I'm working on is being that not only that connective tissue, but then finding ways to leverage the strength of the mothership, if you will, to then accelerate the Intuit mailchimp division. The other thing that we're focused on is how can we ensure that, that from a technology and capability perspective, we're leveraging the great wealth of everything from the engineering skills and capabilities, the marketing skills and capabilities, and taking that power and bringing it to life to drive the Intuit mailchimp business harder and, and sort of faster. So looking at ways that we are doing that are things that I'm, you know, continue to work on. And then to be honest, how now that we are open, just really in. I've been working on how I'm engaging with those next level ventures. Right. What, what that next level down is because for the first few months when we were all closed, it was Covid. I didn't have that, you know, that similar opportunity. But now that we do have that opportunity to get together at work, how we're creating that community because there is power that comes from those hallway conversations and so driving that encouragement to having people come in, having that conversation, having the workshops together, the whiteboard, you know, is a powerful thing to write on together collectively. I'm trying to continue to build that sense of the community.

[Cameron Herold]

Are you having people come back into the office now? Is it a requirement? Is it more optional? What's the, what's happening?

[Sheldon Cummings]

Yeah, so we are, we're, we're hybrid in the way that, you know, we approach it. I think that's similar to lots of other companies. We are not, you know, you know, mandating that people are in their office five days a week or anything like that. But it's more about within that hybrid space and in that hybrid Opportunity. It's more about how we're creating those moments of connection that honestly, people value once, once they are in a few times they're like, oh, I missed this. Yeah. Oh, I missed these conversations. And so that's what we're trying to foster.

[Cameron Herold]

Yeah, that's what I'm hearing and seeing as well. All right, I want to go back to the 21, 22 year old Sheldon. You're just kind of graduating college. You're going to go off and start in your first career job. What advice would you give the, the young Sheldon?

[Sheldon Cummings]

Oh, that's a good one.

[Cameron Herold]

It's advice that you know to be true today. Right?

[Sheldon Cummings]

Yeah. No, I love it. You know, I would say so often I've been very driven by the, you know, so the result, if you will. So whether that result be that grade, you know, within school and I kind of blame my mom because she was always one that was on me. But stuff but the grades within school or, or the impacts, you know, on the business. And I think one of the things that I would encourage the, the younger me is to sort of pick your head up from time to time and what else can you absorb? Work. Right. Are you truly getting as much as possible from the various cities that you're living in or the various people that you're bumping up sort of against? And are you maintaining a lot of those connections, relationships over time? And so I would, I would push him to, to do that because there's robustness of the collection of experiences that I've had over time where I've been so focused on the outcomes, whether it be career or sort of business mind. So that's why I would push him on.

[Cameron Herold]

I love that Sheldon Cummings, the COO or Chief Operating Officer for Intuit mailchimp. Really appreciate the time today on the Second Command podcast.

[Sheldon Cummings]

Well, thanks so much, Kendra.

[Podcast Announcer]

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