The Best CMOs Don't Have All The Answers. They Ask Better Questions.

Marketing leaders are expected to deliver growth, align with sales, lead high-performing teams, and adapt to constant change. But where do you start?

In this episode of Marketing in Progress, Gayle Kalvert sits down with Michelle Randall, CMO at Onspring, to discuss the leadership habits, customer-first mindset, and practical strategies that have shaped her career—and why the best marketing leaders spend more time listening, and asking questions, than talking.

In This Episode You'll Learn: 

• Why every new CMO should interview 30 customers in their first 30 days
• How to build stronger alignment between marketing and sales
• The difference between managing people and leading them
• Leadership practices that help teams grow and perform
• How to use AI thoughtfully without losing the human touch

Highlights:

• 00:00 The legacy Michelle hopes to leave through mentorship
• 01:59 The "30 Customers in 30 Days" CMO playbook
• 05:55 Demand generation and sales alignment
• 11:37 Leadership lessons for building stronger teams
• 16:57 Mentorship, AI, and the future of marketing leadership

Resources Mentioned:

• Michelle Randall on LinkedIn
• Onspring
• She Leads Tech
• Marketing in Progress Community

🎧 Enjoyed the conversation? Follow Marketing in Progress on Apple Podcasts, Spotify, and YouTube for more practical conversations with today's marketing leaders. Join the discussion and stay connected by following us on LinkedIn, and share this episode with someone who'd benefit from it.

Transcript

SPEAKER_00 0:00

My dream is that every one of the women that I mentor pays it forward to the next woman and the next woman and the next woman. And so the legacy I hope to lead is this beautiful network of women supporting other women. Nothing would make me happier than working for a woman that I once mentored.

SPEAKER_01 0:19

Welcome to Marketing in Progress. I'm Gail Calvert. This show is for B2B marketing leaders who are under real pressure to deliver results without a clear roadmap. Each episode is built to give you practical insight you can use right away. We focus on what actually matters, how success is measured, and the decisions and trade-offs necessary for success. If you're trying to cut through the noise, do better work, and build credibility inside your organization, you're in the right place. Let's get into it. Hey everyone, welcome back to Marketing in Progress. I'm your host, Gail Calvert. Today I'm joined by Michelle Randall, CMO at Onspring. Michelle is a proven leader in B2B Tech with more than 15 years experience driving revenue growth and building powerful customer-centric brands. During this conversation, we'll explore how to build marketing organizations that deliver both measurable growth and meaningful customer experiences. Equally as important, Michelle shares with us how she mentors and fosters team member growth. I can't wait for you to hear from her. Let's get into it. Michelle, thank you for being here.

SPEAKER_00 1:28

Oh, it's a delight. Thanks for having me.

SPEAKER_01 1:31

And I'm really excited about not just the marketing we're going to talk about, but mentoring. No, you're really passionate about helping mentor professionals. So that's something near and dear to my heart. But let's start first with something that you've shared with me, which is a playbook that you use each time you have taken on a CMO role. Can you tell us about this playbook? What is this all about?

SPEAKER_00 1:58

Yeah, so I feel really strongly that when you start in an organization, you should stay quiet a lot and you should be asking many, many, many questions. And so I try and really take that to heart and listen a lot when I first begin at an organization and don't make any assumptions. One of the things I always do is interview 30 customers in 30 days because then as I am making conclusions about the business, about some of our opportunities, about some of our challenges, I'm coming from a place of knowledge that is not necessarily in company or tribal knowledge, but hey, I heard this from this customer, and this is one of our largest customers, and here's what they said good, bad, or indifferent. So I try and always do that. I made the mistake of walking into organizations and having a way of operating from my previous one where I'm like, oh yes, I've seen this before and I'm gonna immediately fix it. And what I think sometimes then you forget is every organization is its own beast. And what worked really well, even if the organizations are the exact same size and makeup and even industry, they're still really, really different. And so you have to spend a lot of time in addition to listening and talking to customers, 30 customers in 30 days. I get on and listen to support calls, listen to sales calls, I go on demos, I go on ride-alongs. Anything that gets me closer to the customer to hear exactly what the customer is saying about our solution, about our company and about our people, because that lets me form a playbook for growth and thinking ahead to say, okay, what do I now need to do as a leader?

SPEAKER_01 3:54

I love that. I also think it's important for people to know that you don't have to show knowledge by speaking. I think when we're junior, when we're more junior and we're stuck into these roles for the first time, we think you need to come in and have all the answers. And what you're saying, and what we learn a lot of the times, is won't fill in the silence all the time. Let the silence be there for a second. What comes to the forefront? Is there anything that's been really surprising to you in that playbook experience?

SPEAKER_00 4:26

He has actually. So I won't name names, but I was at an organization a few years ago. And when I asked about the 30 customers in 30 days, it was like going teeth. And it took me probably six months to finish the interviews. It was like, well, this customer has had this issue, so we don't know if we want you to talk to them, like all of that. On the exact opposite end, when I started it on sprain, one of the real things that drew me to the company was everyone talked about being customer obsessed and how customers were raving fans. And I did some back channel and I did find that out. But I started and I said, Hey, I talked to 30 customers in 30 days. You know, I worked with RVP of client dev and I said, Hey, can you give me 30 customers? I had so many that I had to say, please stop. I can't reach out to all of these people. And every time I got on the phone, they would start with, We love Onspring. And I was like, holy Moses, it was such a great start to my entry into Onspring. And it gave me a playbook of how can I take advantage of all of that customer evangelism that's just sitting there? Like, what are you afraid that they're going to say? Or how could my questions, because I don't ask like super invasive questions. I just ask questions like, why did you choose us? What else did you consider, et cetera? They're kind of benign and they shouldn't cause a customer to like run from me screaming.

SPEAKER_01 5:54

Yeah, that's terrific. So you grew up in demand gen, which again, Michelle, we have so much in common from a marketing and leadership standpoint. Like Demand Gen and aligning marketing and sales is where my heart is. That's how I grew up professionally. I can say with our clients and the conversations I have with marketers, it's like there's so much pressure on marketers to drive pipeline and to attach marketing to revenue. How do you feel about you know demand gen and how do you think about that today in 2026?

SPEAKER_00 6:26

Yeah, so I love demand gen. And, you know, often as a CMO, you have to straddle three main areas. And if you're new to an organization or if a recruiter is reaching out, the first thing they'll ask is like, where are you really shine? Is it product? Is it brand? Is it demand? And ideally, as a CMO, you need all three. Like you really have to have a strong foundation, all three. But the reason I love Demand Gen is I actually was in sales for about seven years of my career. And so I have an incredible amount of empathy and understanding for folks that start every month at zero or every year at zero and then have to build as they go. The other thing I love about demand is you get to see the impact of what you're doing like every day. Like the scorecard doesn't lie, and the pipeline doesn't lie. And seeing the pipeline you you're you've built turn into sales and revenue is just amazing. You're like, ah, that person came in and then they went to a webinar and then they read this white paper and they did all these things and all of the marketing touches. And you're right, there's never been more pressure on marketers to deliver. And I think core to being a successful CMO or a successful marketer is deeply aligning yourself with sales. So I talk to my, you know, sort of like left arm, right arm, my CRO almost every day about something. And whether it is like, hey, this territory is is struggling a little bit. We have this opportunity with a partner. What are you thinking? Hey, we need to change the way we're qualifying things, like whatever it is, she and I, and we don't always agree, but we have a tremendous amount of respect for each other. And we each come to every meeting assuming the the best, never assuming sort of ill intent. And I think that is really key to being successful, having a successful partnership.

SPEAKER_01 8:33

I would love to dig into that a little bit more, if you don't mind, because we hear a lot about this and that it can be difficult. What if you were any advice for marketers who are in an organization where they might not be set up that way or they might not have that trust or they're new? What are your best pieces of advice to marketers who want to get more aligned with the sales function?

SPEAKER_00 8:56

First and foremost, assume good intent. So I think often, and especially in a remote world where we're communicating over Slack or over email, you can read things in that probably aren't there. Second is when you're in an interaction and say someone comes at you and they're like, I hate this campaign. This is stupid. I don't know why this isn't what we do. This isn't who you know, like that happens. And asking lots of questions coming from a place, it it's hard. We all invest ourselves and our personal gumption for what it's worth into anything that we produce, right? But you have to distance yourself enough so that you can really hear what someone is saying. So it's like, help me understand. Like those are my favorite words to say. Help me understand why you think this misses the mark. Help me understand what you think might have been better, help me understand how I could have gotten your feedback earlier in this process so that we didn't get to something that was done that you now really don't like. And then the other really important thing, in addition to being like open and transparent, is your word is everything. So make and meet commitments. If you say you're gonna do something, if you start letting your commitments go early on, then you're not trustworthy. And it sounds so basic, but if you say, hey, I'm gonna deliver you X, and instead I deliver you Y, like that's just a terrible way to form a partnership. So whenever I have been anywhere, I never ever ever. My golden rule, like, you know, your golden rule is do you want to others as you want them to treat you? But my golden rule is you never throw sales under the bus. Ever. Ever. Like you work with sales, you talk to sales, you communicate, you're transparent, you have one-on-one conversations all the time. But when you're in a meeting and if someone's like, why isn't this working? What is going on? You never ever say, Oh, it's these folks over here. And to add to like that, help me understand, I think it's an opportunity to get curious. So, like approach the conversations you're having with curiosity. It's easy to go into defensive mode, but if you if you just change, as if you're writing a story and you're interviewing someone, help me understand your point of view, help me understand where you're coming from, help me understand why this matters to you. It produces so much more productive conversations.

SPEAKER_01 11:38

Are you a marketing leader in B2B Tech? Do you want to hear what your peers are actually doing, what's working, what they're ditching, and how they're navigating the pressure we're all under? Well, you're in luck. We just launched the Marketing in Progress community. It's a space for sharing ideas, learning from your peers, and having fun along the way. Visit creocollective.io forward slash marketing in progress to learn more and join us. Yeah, and that leads us directly to mentoring, because you mentioned the same to me, right? When you were younger manager, perhaps you didn't come into that role exactly as in an understanding way, should we say?

SPEAKER_00 12:20

Or well, tell us how to how I sort of want to write, or maybe I should reach out and make amends to people I managed early in my career because here's what happens: you you do really well in your job, and then as a reward, you get to manage people. And but nobody teaches you how to be a good leader. And being a manager and a leader are two very different things. And the way I be a manager is someone who's like, I am following up, Gail, like, did you do this, did you do this, etc.? Like almost like a micromanager. A leader is somebody that inspires the team to do better and be better and removes roadblocks and is there to serve the team, not for the team to serve them. And so, yes, over time, I I learned a ton. I've had some amazing leaders that I then tried to emulate. I've also early in my career, I had someone say to me, a manager at the time or a leader at the time, said, People aren't going to want to work with you because you sometimes come up as the smartest person in the room. I will tell you at first, I was like, Well, sometimes they're idiots.

SPEAKER_01 13:39

Sometimes I am the smartest person in the room. Right.

SPEAKER_00 13:41

Well, but sometimes, and she was like, Yeah, but like you're not being able to collaborate in that way. And like people can read your face, like, my face gets me in so much trouble. And so instead, I think it goes back to coming from that place of curiosity and not assuming that you know all the answers.

SPEAKER_01 14:01

So, can we get practical from a leadership perspective? What do you do? Do you build in moments? We're all busy, right? We want to be great mentors, we want to lead teams, we also have a time to get done. How do you make sure that you're actually, you know, practicing what it is you you'd like to do? But we sometimes get off track.

SPEAKER_00 14:22

So for me, I have a couple of rituals. One is a weekly stand-up with the team so we can all share what we're working on. What are the top three things you accomplished last week? What are the top three things you're going to accomplish this week? And how does it relate to everybody else? I never skip my one-on-ones. If I do, there's something like I had to, had to, but though that I try and hold that time as sacred. Or if I have to reschedule, I always reschedule for the next day. And I have one-on-ones. And the one-on-ones are not for me to say, hey, Gail, take me through what you're working on. It is a time for people to come and say, I am blocked here, I need your help here, or I am struggling to prioritize this versus this versus this. Can you help me prioritize that more effectively? It's all about the people. The one-on-one is for the person that you're having it with. It is not for you as the leader. So it is to remove roadblocks, it's to listen. Sometimes it's just to listen. Like, hey, I'm having a really rough time right now. I just went to this event and it was rough, and the shipping didn't go well, and they didn't put us where they wanted to, and you just need to listen. And I think also as a leader, you constantly need to be self-reflective. So I had an experience a month ago where I didn't show up for someone on my team the way they needed me to. And I heard about it, and I went back to her and I said, Hey, I heard that you said this kind of crappy thing about me, quite honestly. And tell me more. And she was so like, Oh, I'm so sorry. No, I said, No, I'm not coming back to you because I'm angry. I'm coming back to you because I want to be better and I want to show up better. So tell me how I could have supported you differently. And I'm really sorry I missed the mark. And it ended up being a really good conversation, and it helped me learn. You're always trying to figure out what makes people on your team click. And it helps me understand, like for this particular person, I need to show up sometimes in a different way. I sometimes worry more about how to get the work done than the emotions that might be behind it. And so it was a moment for me to stop and say, I need to be better.

SPEAKER_01 16:36

I think everyone who works with you is very lucky. Oh, that's really kind. Really, really kind of you to say. I think a lot of people listening are probably wondering, well, where can I go and have a team like that? Right. Because you never know what you're gonna get. That's terrific. So you mentioned to me that one of your goals is for the particularly women. We we want to help everybody succeed and be successful in their careers. But I think both of us realize that women do need, I think, more support and more of like a spotlight shown on them oftentimes, kind of helping women realize how much success they can have and supporting them. Tell everyone what you told me. Your goal is that every woman that works for you does what now?

SPEAKER_00 17:23

My dream is, and it's not just women who work for me, it's women who I nunture. So I feel like it is my personal responsibility as someone who has risen up the ranks and been really fortunate in my career and had some amazing mentors in my life to reach my hand behind and pull up women to stand alongside me and then go past me. And my dream is that every one of the women that I mentor pays it forward to the next woman and the next woman and the next woman. And so the legacy I hope to leave is this beautiful network of women supporting other women. Nothing would make me happier than working for a woman that I once mentored.

SPEAKER_01 18:06

One of the things we always like to talk about here is what are we learning about, or what do we want to learn about? Is there an area of marketing right now where you're curious or you're spending time or you'd like to figure it out?

SPEAKER_00 18:19

Two primary areas right now. So we market to CISOs, and I have been trying to enmesh my experience in the CISO experience. And I interviewed a dear friend of mine's older sister who's a uh CISO, and she referred me to a group that is called She Leads Tech, and it's all female CISOs and people who females who are trying to get more diversity in technology. And I've been going to their events, I've been participating in their in their book clubs because it's all I, in order to do my job more effectively, I really need to be in in their heads. And so I've just been really like that's been a major focus for me personally. The other thing is I can't believe so much time has gone by without us saying AI. I want to use AI as a thought partner, as a workflow and automation tool, as an efficiency multiplier. But I need to make sure across our organization that we still are human and it's still humans that are producing our content. And ultimately it's humans that are buying our solution. So I have to be very, very diligent to make sure that we don't over-AI anything and that we leverage AI where it makes sense and make sure that we have humans in the process and in the loop where it also makes sense.

SPEAKER_01 19:54

Well, Michelle, every single thing that you said today literally is a reflection of how you are uh connector first. And I really learned a lot from our conversation, and I love getting to know you better. I know our listeners will too. Thank you for spending time with us. Where in the digital world can everyone find you?

SPEAKER_00 20:13

Owen on LinkedIn under Michelle Randall, or you can go to our website on Spring.com, or I'll see you at an event if you're a marketer. Okay, excellent. Well, thank you so much, Michelle. We'd love to have you back. Thank you. I would be delighted.

SPEAKER_01 20:28

If this episode was helpful, please follow Marketing in Progress and tap like. It helps other marketing leaders find the show. And if you know someone who's navigating similar challenges, feel free to share this episode with them. Thanks for listening. We'll see you next time.