Summer Story Series - the Simple Pin Team - Simple Pin Podcast: Simple ways to boost your business using Pinterest

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Hey there and welcome back to another episode of the Simple Pen podcast. This is part three of our story series, our wrap up and I wanted to highlight those who make this company run, the women who show up every day to manage accounts, manage teams and market this company, to test out theories and continue to contribute their time and talents to make this agency run. I thought about how this would be received by you, the listener. Would you care? Is it interesting? Are you curious? My first thought was not so sure. I've done stories in the past about how I started the company, how I built it, but I haven't really gone into team. My second thought was, but this is the story of how the company works, why this podcast is exists, why we keep innovating on Pinterest marketing. It's the why and the how that most people actually never see. Frankly, I came with this idea. This idea came to mind while I was falling asleep. I had been searching for someone to interview for our last story series podcast and either they weren't available or it just wasn't going to work out. And so I felt like sometimes when you can't figure out an idea, it's because there's a reason. So this one popped up. So I started to recount all the people on my team, their years of experience, their stories, and the way in which they've all stayed here, despite the ups and downs, especially of the last three years. Now, the company has been existence for 11, but the last three years have been the hardest, as with many businesses. So yes, I could continue to search around for someone to interview and their story would be amazing. But why not tell the stories of the people who work so hard to bring you the best Pinterest marketing, service and education? Alrighty, let's dive in. The Simplepen team is made up of all women. Now, I didn't set out to design it this way, but it kind of just happened. And majority of us live in the Pacific Northwest. We did have one male contractor at one point, but right now it's all women in the company at this point. We are moms, we are sisters, we are daughters, we are grandmothers and wives. The youngest person on Our team is 25 and the oldest person is 64. The longest team member has been with me 10 years and the shortest three years. No one person has the same schedule on our team and the flexibility to work any hours is always encouraged. Whether team members work in the early hours of the morning or late at night, even during nap time, it's been set a time or two that if only people could see or hear our conversations, then they would know how much we dedicate our time to serving clients and serving our community. That in moments where we just can't jog the traffic on Pinterest to start trending upward again, we are grieved, we are saddened, we are frustrated and wish we could do more. We don't give up at this point. We keep digging, we keep trying. Even sometimes long after the client has given up themselves. Sometimes we just can't be defeated. However, when we discover a new tactic works, we celebrate that win. We celebrate the big wins and the small wins of each and every one of our clients and people in our community. Even though it's small, we want every single client to experience growth. But there are moments when we question ourselves, when we wonder if we're confused. Even though we've done something a hundred times, we will look at it and say, I think I know the right answer. I'm pretty sure we just need the rest of the team to affirm where we are at. Some common phrases we have within our team are one. Fail forward. Each failure is an opportunity for growth. That each moment has learning and value for us to better ourselves. We acknowledge our mistakes, but we are intentional about learning learning from them. The other phrase is build the plane as we fly it. Four years, new services, new memberships, new systems, we would feel like we were building a plane as we flew it midair. Those times are less frequent now. Thankfully, the team is breathing a sigh of relief. But we know that at each turn there might be something new where we have to build the plane as we fly it again. We know we want to accomplish something. We are driven to get there, but we don't always know the system. System is so important here at Simplepen. And it's our system. It's a system that works for us and it works for our clients. No one system is the same and it is not modeled after any book or anything else. It is the system that is the simple pin way. This allows us the freedom to be a little bit messy as we grow. Our core values have shortened from 7 to 5 to 3 because frankly, no one in a company has time to remember seven core values or even five. There's an abbreviation we use, I see you Initiative Communication. Uplifting Communication is my number one on the strengths. Finder communication was core to my everything. When I started this company. I wanted every email, every interaction, everything we were sending to the clients to be clear, to be concise, and to be quick. There is a rule here, that 24 hours is our threshold. Within 24 hours, we want to be getting back to a client and if we don't know something or if we're on the receiving end of a really upset client email, which thankfully doesn't happen often, our first response is to say, I've received your email. I'm going to take a little bit of time to dig into this and I will get back to you within 24 hours. That's the same with a customer service email or anything else. Initiative is also really important to us. We want to take the initiative. We don't want to wait for someone else to do it. We want to combine both our creativity as well as our ideas to lean into something that goes back a little bit to build the plane as we fly it. We've got to have initiative to build the plane effectively and uplifting. That is so important on this team. We sometimes get so busy that we forget to do shout outs. But we have an employee of the month every month where we nominate them. We have this thing called Frog Fridays where we forever recognize other people's greatness, where we call out the work. And this doesn't just happen on those assigned days. But even just yesterday, I saw somebody call out two other team members for doing such a great job within one of our programs to really affirm that they had seen their hard work, they had seen the dedication that they put in. You cannot have a really great and amazing team without this part. So I want to introduce you to these amazing team members. They have names, they have families, they have lives. And sure, I could just talk really high level about them, but I'd love for you to meet them and I'm going to tell their story. Leslie is my chief operating officer and integrator. She is my sounding board, my gatekeeper, and she has been in this role for the last five years. She is the person that can read me, understand me the most. And it has been a gift that is not lost on me that she is able to do that. Not every CEO is this fortunate. She started at the company as account specialist. She actually didn't even know that she was in an interview. That was about nine years ago now, almost 10, I believe, and has worked her way up to this position. Some of you may have even met her at conferences. I think this position is so important for me because I have had in the past a tendency to go on my first idea. And sometimes your first idea is not the best idea or sometimes your first instinct is not the best instinct. So she Allows me the buffer to throw all of these ideas out there. And it is very common for me to be so passionate about something and be so eager about it. And then I say, okay, let's wait a week. And then next week she's like, hey, what about that idea? I'm like, oh, I totally forgot. I don't care. I think that's very true to an entrepreneur, right? Is that we are very excited in the moment, but when it gets down to boots on the ground, eh, maybe it's not that important. We have two other directors on our team. Risa is the director of services. She is the one who takes care of that part of the team. She assess the situation. She keeps track of progress. She works with the discovery call team to coach them on having better calls. She works with account specialists and primarily with our team manager, Sarah, who I'll talk about in a minute. But Rissa kind of has overseen all of this and she has actually started as an account specialist too. Worked her way up to being a team lead and then team manager and then services director. Erin is our director of Pinterest advertising and design. She is deep on all things Pinterest ads as well as using her creative skills within the design of new pins. Erin is passionate about her clients and loves to watch them succeed. Her favorite abbreviation is Roas. Roas return on ad spend. We like to do a lot of creative things to really succeed. On the ad side. She is very picky about the clients that she works with because she wants to to ensure that we can really help them succeed. And she has knocked it out of the park for some of those clients. So we're very excited to have her brain in this section of our team because if we did not have Pinterest ads, there wouldn't be this good, like crossover between organic and ads. Sarah is the team manager and if you've ever been a part of the inner circle, she's also the lead in that group as well. She is so great about supporting the team with education, testing out certain things. And she actually is the catcher of a lot of my crazy ideas for things I want to try. When it comes to Pinterest marketing, she's the one I go to when I say, hey, Sarah, I'm thinking about this, or what do you think about this whole board section thing? Or what do you think about this whole theory that's kind of over here in the ether? Like, let's bring it all together. I want to see if it works or not. And she's a willing and helpful participant who can also be really honest to share with me whether or not it's a waste of time or whether or not it's worth it. And I love having this here because Sarah not only has clients of her own and also works with the inner circle and also oversees the team with their clients. But what I love about it is that she can be transparent with something to say like, ah, this is not going to work, or I tried this tool. Sarah tries a lot of tools for me and she will find places where they are lacking. A lot of people will send us their tools. We don't test out all of them, but it might be certain new features on Tailwind or there might be a new Pinterest AI tool or something like that. We want to be the first on the ground to test it before I talk about it. So Sarah's really great to work with those things. I'm going to breeze through a few of these a little bit quicker, but that doesn't mean they are less important. Becky, who works on our image team is also a team lead. She's really familiar with E commerce side of Pinterest and working with our clients. Rosanna, a faithful and dedicated account specialist that's worked with some really tricky accounts. Megan is also an account specialist, but she manages our vacation floaters. This is essential because when a team member needs to take a vacation, we need to have floaters to fill in and watch over those accounts. Megan ensures that happens. That is incredible. Jolene wears many hats from analytics to account specialists to image team and now supporting our ADS team as we gain more clients there. Carrie is an account specialist that always gets great feedback from clients. She's curious, she's hardworking, she has a lot of accounts to juggle. Jenny was actually my second hire on the team and has been a long time really faithful account specialist and loves her work with clients. Amy is our operations specialist. I think there's probably a better name for it, but I'm just gonna say operations. She is the one who has to build the plane as we fly it sometimes, which God bless Amy. She onboards all of our new clients from invoicing to handing off the team. And actually she also helps with payroll and she doesn't run payroll for the team, but helps with those pieces. Helps with some HR pieces. I cannot tell you how many times I will get something from our insurance company or from some state and something has screwed up and Amy has to be on the phone with them. Amy is detailed, she goes deep because these are some parts of Running a company that people don't think about when they have employees. You don't think about all these updates to these plans, you don't think about these updates to retirement plans. Like those have been some of the biggest headaches. And Amy has beared that burden. And that is incredible because I, I have a hard time calling the pharmacy to figure out my prescription, not because I can't do it, but because I get annoyed too fast. So Amy has the dedication to go the distance here, which is just incredible. Emily, she manages the discovery call team as well, alongside Rissa, our services director handling audits, strategy calls and is incredibly supportive and another mentor in our inner circle. She is a new mama and so she's juggling both work and having a baby at home. She's our latest baby here at Simple Pen Media for sure. Um, many have gone before her on the Simple Pen team, so we understand working with a baby, maybe you slack at weird times, answer emails in the middle of the night. Grace and Nikki. These two are the greeters at the door of our company. As the discovery call team specialist, they have a front row to see all the people interested in our services. They ask questions, they get curious, they look for ways we can serve people. And they are nice. Never afraid to say no if a client isn't a great fit. But they will always be diligent in looking for ways that we can serve clients. We touch base every single Monday about what's happening on our discovery call team. Emily runs that snap report for us to tell us what's happening, how many calls we have. Surprisingly, we have a lot of no shows sometimes, so we keep track of those too. So just note, if you ever book a call with somebody, cancel the call, please. That'd be so great. Not just for us, but for other people. And last, the marketing team, Amanda and Daphne. These two are our powerhouse. Daphne wears many, many hats. She's an account specialist as well as managing the Simple Pen shop as well as doing analytics and answering questions from our customer support email beautifully, even if they are a little bit off. She's quick, she's fast and she's curious about all the things marketing and how to optimize. Amanda is a marketing team admin. She makes all things run on the marketing side. Her love language is efficiency and great customer care. I'm sure I drive her nuts overlooking details. And yes, Amanda know I know I haven't re recorded that video. Just need to make that public. Our marketing team meets twice a month and we're always talking about ways to serve people better, make sure we are relevant and not wasting our community's time. This team is the lifeblood of Simplepen Media. Sure, I get to be on the mic, I get to be in these videos speaking on stages, but they care so deeply about our clients, our listeners, our buyers. They care that what we share at Simple Pin Media is business building and it does not draw attention away. We constantly ask ourselves questions if we're better at something or if we're just chasing something because the crowd around us is doing it. When a team member leaves Simple Pen, we have a tradition. We give notice in Slack, make sure everyone supports them, and then the day after they're done, we send flowers so they show up at their door. Even if people have left our team on more of a sour note, which again, thankfully, that has not happened that often. But we want to finish well. I know building a team is not on everyone's list of goals for their business, but if I had to share a few resources that have helped, here's a few that have worked best, I would. I didn't add this actually to my notes, but I'm going to add this right now. You have to be willing to allow people to make mistakes. And if you are somebody that is hyper controlling, you are hyper gatekeeper, and you are so afraid of people making mistakes, this will not work for you. You cannot build a team if you are unwilling to have a motto like we have, which is fail forward. People are going to make mistakes. How they respond to those mistakes and how you respond will build this amazing culture in your team that it is a safe place for them to do that. And I find that a lot of people who think about scaling an agency or hiring more people, they just think everybody can do it. And it takes time to finesse that, to figure it out. So right off the bat, if you're thinking, man, I need all the control. This might not be for you to hire a team, but if you're somebody who can kind of let that out a little bit, maybe you can. These two books have been essential. One, the Ideal Team Player. I'll put these actually in the show notes. There's also a YouTube video you can go watch as well. I'll put that in the show notes. This has revolutionized the way we hire, the way we fire, and the way we evaluate our team. Hands down, best book I've ever read. The Ideal Team Player. He has other books as well. They are written in a fiction format and then they go into some practicalities at the end. He also has five dysfunctions of a team and a couple others. I I recommend all of them, hands down the best team books I've ever read. The next is Traction. This is dry and this is for a specific type of company. If you are a fairly large company, you're doing a large amount of revenue, you have a lot of people and you feel like things are just a little bit out of control and you need to pull it all together. This is a teaching on the entrepreneurial operating system eos. Actually how I discovered that Leslie was the person I needed to hire as my integrator, my chief operating officer was was through reading the sister book Rocket Fuel. It talks about visionary integrator, those two kind of that suite of books in the traction space is really good for creating structure. Now it is very detailed again and it is very dry. It isn't for everybody but for us. We have taken and we now run on a modified EOS system for our meeting case cadence and our accountability structure. This really works for us. Last I feel like I made a conscious choice in the beginning to train people in a way that will allow them to be creative, honest and always getting better at their job. I promised I wouldn't nitpick them, but I would ask questions and attempt to see their perspective. I would be honest with my shortcomings even if I didn't always see them. I have been far from perfect, but I want to always remain teachable and kind to the team that is working for me. I have no idea how many more years Simplepen Media has. I hope many, but sometimes it's not up to me. However, whatever may happen, I always hope that the Simple Pen team will remain strong, educated, joyful and driven to succeed. Thank you for allowing me to share their story, to share who they are. So when you listen to this podcast in the future, think about all the people that are in this, that make this company run and think about their investment. And then it's not just me who's doing all this education, but it's all the people behind me who are gathering all these ideas, testing, doing all the stuff. And thank you again for listening to this story series Sam.

Detailed Summary of "Summer Story Series - The Simple Pin Team"

Podcast Information:

Title: Simple Pin Podcast: Simple ways to boost your business using Pinterest
Host: Kate Ahl
Episode: Summer Story Series - The Simple Pin Team
Release Date: July 23, 2025

I. Episode Overview

In the episode titled "Summer Story Series - The Simple Pin Team," host Kate Ahl delves deep into the backbone of Simple Pin Media—the dedicated team of women who drive the company's success. This third installment of the story series shifts the spotlight from Kate's entrepreneurial journey to the individuals who manage accounts, lead teams, and innovate Pinterest marketing strategies.

II. The Heart of Simple Pin: The All-Women Team

Kate emphasizes the unique composition of her team, highlighting that it consists exclusively of women. This was an organic development rather than a deliberate strategy. She states, "The Simplepen team is made up of all women. Now, I didn't set out to design it this way, but it kind of just happened" [04:30]. The team is diverse in age and experience, ranging from 25 to 64 years old, with the longest-tenured member having been with the company for a decade.

The majority reside in the Pacific Northwest, fostering a close-knit work environment. Kate underscores the team's flexibility, allowing members to work unconventional hours to balance personal commitments, which has been crucial especially during challenging times over the past three years.

III. Company Culture and Core Values

Kate elaborates on the resilient and adaptive culture at Simple Pin Media. She introduces two key phrases that embody their approach:

"Fail Forward": "Each failure is an opportunity for growth. That each moment has learning and value for us to better ourselves" [25:45]. This mindset encourages the team to view mistakes as stepping stones rather than setbacks.
"Build the Plane as We Fly It": Reflecting their dynamic growth and constant innovation, Kate explains, "Four years, new services, new memberships, new systems, we would feel like we were building the plane as we flew it midair" [29:10]. This adaptability has become less frequent but remains a foundational aspect of their operations.

Kate also discusses the importance of their unique system—the "Simple Pin way"—which allows for creativity and flexibility while maintaining effective structures. Over time, their core values have been distilled for clarity and easier recall, with a strong emphasis on communication, initiative, and uplifting interactions within the team.

IV. Meet the Team

Kate takes listeners on an introduction to each team member, showcasing their roles, backgrounds, and contributions:

A. Leslie - Chief Operating Officer and Integrator

Leslie serves as Kate's sounding board and gatekeeper. With nearly a decade at the company, she provides stability and invaluable insights.

"She is the person that can read me, understand me the most. And it has been a gift that is not lost on me that she is able to do that." [11:30]

B. Risa - Director of Services

Risa oversees the services division, coaching the discovery call team, and ensuring client progress.

"She assesses the situation. She keeps track of progress. She works with the discovery call team to coach them on having better calls." [14:50]

C. Erin - Director of Pinterest Advertising and Design

Erin specializes in Pinterest ads and creative pin design, ensuring clients' advertising strategies are both effective and visually appealing.

"Her favorite abbreviation is ROAS—Return On Ad Spend. We like to do a lot of creative things to really succeed on the ad side." [18:15]

D. Sarah - Team Manager

Sarah manages the inner circle, oversees client work, and tests new tools and strategies.

"She is the catcher of a lot of my crazy ideas for things I want to try. She's a willing and helpful participant who can also be really honest." [21:10]

E. Other Team Members

Becky: Team lead on the image team, specializes in e-commerce Pinterest strategies.
Rosanna: Dedicated account specialist handling challenging accounts.
Megan: Manages vacation floaters to ensure seamless client support during team member absences.
Jolene: Multifaceted role covering analytics, account specialization, and supporting the ADS team.
Carrie: Account specialist known for excellent client feedback.
Jenny: Long-standing account specialist passionate about client engagement.
Amy - Operations Specialist: Manages client onboarding, payroll assistance, and handles intricate operational tasks.

"Amy has the dedication to go the distance here, which is just incredible." [38:40]

Emily: Manages the discovery call team and balances work with her new role as a mother.

"She's our latest baby here at Simple Pen Media for sure." [41:55]

Grace and Nikki: Frontline discover call specialists who greet potential clients and assess their needs.
Amanda and Daphne - Marketing Team: Drive the marketing strategies, manage the Simple Pin shop, and ensure efficient customer support.

"This team is the lifeblood of Simplepen Media." [50:20]

V. Overcoming Challenges and Innovation

Reflecting on the past three challenging years, Kate highlights the team's unwavering commitment to client success. When faced with stagnant Pinterest traffic, the team remains resilient:

"We don't give up at this point. We keep digging, we keep trying. Even sometimes long after the client has given up themselves." [09:15]

Their relentless pursuit of effective strategies leads to both big and small victories, all of which are celebrated to foster a sense of achievement and motivation within the team.

VI. Building a Positive Work Environment

Recognition and support are pivotal in Simple Pin's work culture. The team engages in various initiatives to uplift each other:

Employee of the Month: Regular nominations highlight individual achievements.
Frog Fridays: A tradition of recognizing and celebrating team members' contributions.

"We sometimes get so busy that we forget to do shout outs... But we have Frog Fridays where we forever recognize other people's greatness." [32:50]

Kate underscores the importance of these practices in maintaining a supportive and motivated team environment.

VII. Leadership Insights and Recommendations

Towards the episode's conclusion, Kate shares valuable resources and philosophies that have shaped their team-building approach:

Books:
- "The Ideal Team Player" by Patrick Lencioni: Revolutionized their hiring and evaluation processes.
- "Traction" and "Rocket Fuel" by Gino Wickman: Helped implement the Entrepreneurial Operating System (EOS) for structure and accountability.

"These two books have been essential... Hands down, best book I've ever read." [54:30]

Team Management Philosophy:
- Emphasis on allowing team members to make mistakes and learn from them.
- Fostering an environment where honesty, creativity, and continuous improvement are encouraged.

"You have to be willing to allow people to make mistakes. If you are somebody that is hyper controlling... this will not work for you." [45:10]

Kate concludes by expressing her commitment to remaining teachable and kind, ensuring that the team's culture remains strong and supportive regardless of the company's future trajectory.

VIII. Final Reflections

In her closing remarks, Kate thanks the team for their relentless efforts and dedication. She encourages listeners to appreciate the people behind the services and education Simple Pin Media offers, emphasizing that the company's success is a collective achievement.

"Thank you for allowing me to share their story, to share who they are. So when you listen to this podcast in the future, think about all the people that are in this, that make this company run..." [58:20]

Kate's heartfelt acknowledgment serves as a testament to the power of a cohesive and passionate team in driving business success.

Conclusion

This episode of the Simple Pin Podcast offers an intimate look into the foundational team behind Simple Pin Media. Through Kate Ahl's detailed narration, listeners gain an appreciation for the diverse talents, unwavering dedication, and collaborative spirit that propel the company forward in the competitive landscape of Pinterest marketing.