Sam Chandler Of Zendesk On How We Can Increase Women’s Engagement in Leadership and Management

Despite strides towards equality, women remain underrepresented in leadership and management roles across various sectors. In this series, we would like to discuss the barriers to female advancement in these areas and explore actionable strategies for change. We are talking with accomplished women leaders, executives, and pioneers who have navigated these challenges successfully, to hear their experiences, tactics, and advice to inspire and guide the next generation of women toward achieving their full potential in leadership and management roles. As part of this series, we had the pleasure of interviewing Sam Chandler.

Sam Chandler is a customer retention & engagement expert who has been featured in a variety of articles, podcasts, and digital marketing campaigns about all aspects of concepts of user experience, the psychological drivers behind consumer behavior, and how AI will impact consumer expectations.

Sam has advised hundreds of companies from early stage startups through Fortune 500 corporations on launching go-to-market (GTM) strategies and was named as a Top Voice in Customer Retention by LinkedIn. She thrives on building highly capable & diverse teams and is incredibly proud to have helped dozens of her reports advance into senior positions and into senior leadership roles.

Sam lives in Atlanta where she developed the ultimate brownie recipe and consistently bombards her husband, Carl, with theories about the manifestations of humanity’s collective anxieties through popular horror movie themes and other movie nerd fodder. Rumor has it her personal consumption of sugar free Red Bull has single handedly funded the entirety of Max Verstappen’s left front tires since the 2019 F1 season.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Funny you should ask. Statistically speaking I shouldn’t be here at all. I am the product of a single mom whose entire childhood was lived well below the poverty line and in an extended family with just a couple of high school diplomas between the whole lot of us. Considering that 70% of children living with a single mother are poor or low income and that I had a 3% chance of even finishing college, the fact that I graduated cum laude with a full scholarship from a top 20 university is apparently pretty unheard of. I guess I should probably go buy a lotto ticket!

I entered the University of Georgia as a Drama major. I had no idea what I wanted to be when I grew up, but I knew the things I enjoyed most in high school had centered around my time onstage in our school productions and in my duties as Drama Club president. One time I had a prominent lawyer in my hometown tell me that I would change my major once I “realized I couldn’t get a job.” And he was right — I did change my major. But it was to go from Drama to Film Theory. I’d love to go back and ask him if that’s what he had in mind!

After graduating college, my main objective was to make enough money to support myself. I worked retail throughout my time in school and my mom’s entire adult life had been spent in various retail management positions, so it seemed a natural transition into a steady role with steady pay. Little did I know that being a Guest Services Manager at Target would be foundational in shaping who I am today. It’s where I met my husband, where I learned how to manage a team, where I learned how to handle sensitive customer situations when everything is on fire, and where I learned the extent of what can happen to a public restroom on a holiday weekend.

Since my path was not supposed to lead me here, I don’t tend to plan too many steps ahead of where I am in terms of title. Perhaps it’s my own little slant on mindfulness but while some people are constantly pushing towards their next title, I try to soak in all I can within my current role. It helps me pursue things that I genuinely find intriguing as opposed to swinging from tree limb to tree limb trying to climb some kind of corporate-y ladder-y thing. It also focuses my mindset around becoming a subject matter expert as opposed to being senior-this or VP-that of insert-company-here. Every role I’ve held since Target has been a referral from one of the amazing people I’ve worked with. Which is an incredible honor to say and I believe a direct result of a pursuit of thought leadership, of finding ways to be useful within an organization, and of taking care of the people around me. My most rewarding work these days is helping others realize how to find value in their knowledge and expertise as well.

Can you share the most interesting story that happened to you since you began your career?

There’s no one big eureka moment that comes to mind, instead I find myself with a compendium of seemingly insignificant moments that in retrospect were essential threads in the fabric of my journey. Kinda like a Butterfly Effect situation. One of the most significant insignificant moments for me was someone else’s choice of customer service software. About 13 years ago I was on the operations team for a startup here in Atlanta. We sold these massive industrial-strength surge protector boxes to huge enterprise companies. We were running our business out of Outlook and Excel spreadsheets and customers were falling through the cracks because we had no way of knowing if anyone was following up with their requests. One day our Senior VP of Operations came into my office and said “Great news. Operations is now in charge of customer service. I just bought this thing called Zendesk. Sam, figure out how to make it work.”

This is the 483rd time I’ve told that anecdote. The 398th time I told it, I realized what a pivotal moment that little decision had been in my life — and it wasn’t even my decision! Had my Senior VP used a different platform for customer service at his previous company I wouldn’t have discovered Customer Success, or built any of the programs & teams I’ve built, or have a great anecdote to break the ice with new customers. It’s taught me the profound impact these insignificant moments can have on your life.

Can you share a pivotal moment in your career that significantly influenced your path to leadership?

2020 was a pivotal time in my leadership development. People were scared, they were angry, they were confused and none of us knew what was around the corner. It was in this chaos that I started getting a lot of folks coming to me for guidance on “being an authentic leader.” At first I was confused on what that meant — authenticity is one of those words that gets thrown around and applied to everything. But as I spoke with people I slowly realized they were actually talking about courage.

One of the most important jobs we have as leaders is to help give people the confidence to share their ideas and speak up when something is wrong. It can be really daunting for a team member to share positive things they’re doing, but it’s downright terrifying to have that conversation with their manager when they need help addressing inappropriate behavior or other issues they can’t tackle on their own. Once they do surface the topic they expect their manager to take it to the appropriate channels and be their champion for change. Over the years I’ve realized that many managers don’t have the confidence to be the escalation point for these kinds of issues. They point their team members to HR and think they are done.

Amidst the uncertainty of COVID and all of the social and political upheaval, it was a time where people were trying to find their voice. When someone asked me about being authentic, they wanted to know how I was able to find the courage to speak truth to power when something needed to change. I’ve kept the lessons of that period with me as I advocate for people who need a voice and mentor others to find the same courage as they’re becoming leaders in their own right. One of my former reports was just sharing a story with me about how she defended the needs of one of her reports and I was so proud I almost started crying!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

It’s so true! It absolutely takes a village. So many people have supported me and allowed me opportunities I wouldn’t have otherwise had. Over the years I’ve learned really important lessons from leaders who taught me how to build authentic relationships while setting boundaries, how to fight and stand up for myself, and how leaders should show people that they’re seen and heard. I’ve also learned a lot from the people I’ve had the honor of managing over the years. My goal is always to create environments where the best ideas win — even if they aren’t my own. A common theme among my team meetings is “prove me wrong.” This is where I tell them the direction we’re going in but tell them to convince me that their way is better. I’m always thrilled when they do!

If I had to narrow it down to one story though, I’d have to go back to the beginning. I realize that so much of the ingenuity that was fostered during my childhood has found its way into my adulthood. I constantly find myself thinking back to a time in elementary school when my class was having a Thanksgiving celebration and we all dressed like pilgrims. My mom had absolutely no money to go and find anything resembling a pre-made pilgrim costume, so she made a hat and apron from a white sheet and put it over the dress from an old witch’s costume she found in the closet. Not only did I have a pilgrim’s costume, I won the award for best pilgrim’s costume in the class. This is just one example of the times I had to be better while starting from way behind. It’s taught me to disregard anyone’s expectations because I know I’m going to blow past them anyway. Which is exactly what I strive to teach my team members as well.

Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

I’m usually more of a short form and periodical kind of girl, but there are two books in this world that I keep on my phone because I can’t stop quoting them: The Effortless Experience by Matt Dixon, Rick DeLisi and Nick Toman. And Hooked by Nir Eyal.

So often in my profession decisions are made because they sound like a good metric. Or on the opposite end of the spectrum, companies veer so far into their data that they lose the humanity necessary to curate their strategies. I am obsessed with both of these books because they do a wonderful job of balancing both behavior and data. The Effortless Experience has not only shaped how I consult with companies on their customer experience strategies, but I’ve also developed a mini-course I make all my new team members participate in to inform their recommendations to their customers and to hone their presentation skills.

Hooked is about habit-forming. It’s usually sought out by product folks, but I’m obsessed with it because it helped me reframe my mission in Customer Success around what it could look like to build retention & growth models around the goal of generating habitual engagement in order to grow revenue. A couple years ago I got to talk to Nir Eyal during a course he taught on product development and I freaked out like I was meeting a rockstar!

Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?

“While you’re fighting for a seat at the table, I’ll be down in Atlanta building my own.”

–Tyler Perry

Even just saying it now gives me the chills. This was my favorite part of Tyler Perry’s acceptance speech for the BET Ultimate Icon Award in 2019. Watching his career, how he’s done it, and all the folks he’s brought with him along the way is truly inspiring. Forget clamoring for a seat at someone else’s table — build your own damn table! It’s such an important message for women, people of color, and anyone who isn’t intimidated by doing things differently than they’ve always been done. It’s a message that’s made all the more special because I live just down the road from Tyler Perry Studios and get to see first hand all the goodness he’s done for Atlanta and for people of color.

How have you used your success to make the world a better place?

People have done so much to support me throughout my life — including paying my way when I wouldn’t have otherwise been able to join. I try to pay it forward whenever I can by making sure no one is left out of an activity or opportunity because they can’t afford it. I also believe a huge part of leadership is using your voice to highlight others. When you’re early in your career, your impact is largely measured by your individual contributions to an organization. But the further you progress, the more you realize your impact is multiplied by the success of those you’ve supported. This isn’t relegated to people managers either — anyone with a platform is capable of using it to help highlight the impact of those around them. Every time I am able to celebrate someone else’s wins, or use my network to connect great folks to one another, or be a champion for someone who needs a voice, it brings me so much joy to be able to support others as I was and still continue to be supported. When you put goodness into the world, it comes back to you tenfold.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this report, only about 31.7% of top executive positions across industries are held by women. This reflects great historical progress, but it also shows that more work still has to be done to empower women. In your opinion and experience what is currently holding back women from leadership and management?

Ourselves. I know that sounds controversial but hear me out. Women are less likely to be in top executive positions because they are less likely to be promoted in the first place. Women are less likely to ask for promotions and negotiate for pay raises because gendered politeness is socialized in us from an early age.

I’m reminded of the famous Sandra Day O’Connor quote “the first but not the last.” She graduated from Stanford Law in the top 10% of her class, but couldn’t find a job because in those days law firms didn’t hire women. Instead of taking the more “gender-appropriate” secretary role offered by one of the firms, she worked for free for the San Mateo County District Attorney’s office until she was hired as the deputy district attorney and began her pursuit towards becoming the first woman appointed to the US Supreme Court.

We know the cards are stacked against us. If we want to redefine the status quo we have to push the boundary ourselves. This means having to be what we can’t yet see. The more women blaze their own trail and redefine what it means to be a leader, the more we reshape society’s views on what a leader can be and in turn establish a more equitable foundation for those who will follow.

This might be intuitive to you but I think it will be helpful to spell this out. Can you share a few reasons why more women should become leaders and managers?

Yes it should be intuitive but unfortunately it still has to be spelled out: Diverse businesses do better. A 2020 McKinsey study revealed a massive 48% performance differential between companies with the most and least gender-diverse executive teams. This doesn’t just apply to gender-diversity either. Nonhomogenous teams of ALL kinds perform better because they’re smarter. They focus more on facts, process those facts differently, and are all-around more innovative. This is because they break down the stale thought that non-diverse groups can fall into when they don’t consider problems from new perspectives.

Mark Cuban said it best: “…If you find the companies who think diversity is a negative, let me know. I want to short them or compete against them.”

Can you please share “5 Things We Need To Increase Women’s Engagement in Leadership and Management?” If you can, please share an example or story for each.

1 . Authenticity — So often we think we have to change who we are in order to be taken seriously or to be seen as a leader. But the behavior of a leader is dictated by those who lead. If we want to increase the number of women in leadership, we have to show them their unique perspective is not only welcome but needed in order to create the diverse teams that will innovate and outperform their peers.

2 . Perspective — Do NOT accept the little victories as winning the war. We still have a long way to go! It’s wonderful to see companies investing in programs to increase participation from women and people of color. But we cannot mistake revised company mission statements as problems solved — there’s still a gap in participation for women in leadership positions. We have to keep going until we’ve neutralized the inequities that still exist for women to progress into these positions.

3 . Allies — Allyship isn’t about the big moments; it’s about the little ones. Oftentimes microaggressions are so common they aren’t even registered as bad behavior but they add up to a profound impact in suppressing a woman’s pursuit of higher leadership positions — even when that impact isn’t acknowledged. Small actions like ensuring women have space to talk during meetings without getting interrupted go a long way towards changing the culture.

4 . Mentorship — Women need mentors in their lives not only to convey advice and experience, but also to empower them to maintain their authentic selves as they progress in their career.

5 . Sponsorship — Mentorship is a pretty well known aspect of increased participation of women in leadership, but sponsorship might arguably be even more important. Sponsors are people who say your name in rooms you’re not in. Guidance is vital to helping women prepare for leadership positions, but there comes a point where we actually have to get women into leadership positions. We need more sponsors!

In your opinion, what systemic changes are needed to facilitate more equitable access for women to leadership roles?

First and foremost: executive adoption. A company can say they’re committed to creating equitable access for underrepresented groups, in fact their mission statement most likely does. But you can tell a lot from a company based on who they’ve put in charge of making it happen. Employee Resource Groups (ERGs) and other employee-led initiatives are great, but equity is like any other goal at an organization. If an executive doesn’t have it tied to their pay then it’s not truly a priority. Don’t let fancy words fool you into thinking otherwise.

We also need more benefits that support women’s needs. Kate Ryder literally founded the Maven platform around the need to support women through their family planning stages and beyond. I’m also seeing options like Carrot Fertility included more and more in a company’s benefits package. While these are larger organizational investments that need to be made and will take much longer to implement, even small considerations like keeping free tampons in the bathroom can communicate that an organization is keeping their female employee’s needs in mind at every level.

We need returnship programs to support women and caregivers in returning to work after gaps in employment. As recently as 2022, the US Chamber of Commerce reported that 32% of unemployed women didn’t return to work because they had to care for a family member. Career gaps are stigmatized by recruiters, and jobseekers have few resources when it comes to articulating the reasons for their leave or demonstrating their transferable skills. One of my favorite and longest tenured colleagues came to Zendesk through a program called Path Forward. She is an amazing asset to our marketing team and I can’t imagine our company without her contributions.

And lastly, we need more research on the impact and handling of microaggressions on women in the workplace. From an anecdotal perspective, I can personally say that microaggressions and poor behavior are often conflated as interpersonal agreements between colleagues. But I don’t see enough research on the topic. McKinsey has studied the occurrence of microaggressions in the workplace — women reporting 2x more comments about their emotional state, and 1.5x more frequency of people taking credit for their ideas or mistaking them for someone more junior. But I’m yet to see any studies on how often these microaggressions are mislabeled as interpersonal disagreements when they’re reported to HR, or if this happens more frequently to women than men. Which is probably because they’re miscategorized in the first place. If someone out there reading this can fix this gap in research, please let me know what you find!

What strategies have you found most effective in mentoring and supporting other women to pursue leadership positions?

The first thing I try to understand is what motivates that individual. Oftentimes we find ourselves chasing titles without even thinking about whether it’s the path we’re interested in. One of the most impactful people in my career has been a previous manager who introduced me to her Motivational Pie Chart exercise. It asks team members to consider what is most important to them in a role and to rate their satisfaction with that component of their current job. I have my own team members do this exercise at least once a year and several of my former team members have taken it with them as they have become managers. Earlier this year I was sitting at a conference with two amazing women I used to manage and have since become senior managers themselves. The speaker on stage started talking about incentivizing employees and both of these ladies turned to me and whispered “motivational pie chart!” I can’t describe how warm my heart was when I thought about how I had passed down the lessons I myself took from the awesome women in my life.

It’s also important for mentors to not only impart lessons, but help their mentees recognize the greatness within themselves. One of the biggest challenges I’ve seen in my team members is not recognizing achievements they consider pedestrian. Helping them articulate those achievements on resumes is great — encouraging them to share their expertise across larger audiences is even better. And shouting their greatness from the rooftops when they’re too intimidated to do so is even better than that! It’s imperative for mentors to use their platform to highlight others. This is where mentorship turns into sponsorship.

How would you advise a woman leader about how to navigate the challenges of being a woman in a leadership role within a male-dominated industry?

Don’t think of yourself as a woman leader; just think of yourself as a leader. Leadership titles don’t come in pink for girls and blue for boys. Be useful, be knowledgeable, act like you’ve been here before. The rest will follow. Are you going to run into people along the way who will try to make it about your gender? Yup. Will you have to work twice as hard to get to the same starting spot as your male counterparts? Probably. Does that mean your own accomplishments will normalize women leadership in your industry and create a more equitable playing field for the next generation? You betcha.

How do you balance the demand for authoritative leadership with the stereotypical expectations of female behavior in professional settings?

Actually, I adore being underestimated. That might sound sarcastic but I truly mean it! The more you’re underestimated the more traction you have to run circles around anyone who doubts you. Nothing I have ever done has been stereotypical and I don’t intend to start with conforming to anyone’s idea of what stereotypical female behavior is. This is why we need more women to come into leadership with their whole selves so that the status quo evolves away from someone else’s view of normal or acceptable.

Leaders lead because people follow them — not because they have a title that says people should. Be authentic. Care about your team. Say smart things. Be useful. Give credit when people do good things. Follow those steps and you’ll never have to worry about stereotypical female behavior in professional settings.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

Well first off, thank you for saying that. It means a lot. As I think about the root cause of a lot of the issues we’ve talked about today, I would love to inspire others to stop being nice. We equate being nice with being a good person when in actuality it means we let issues lie dormant instead of confronting them. Over the years I’ve learned that people will do just about anything to avoid confrontation. Whether that’s standing up to someone who is disrespecting them, or even just rejecting a pushy sales pitch. This can result in some pretty bad things that go way beyond just buying something you didn’t want. Both gendered politeness and the human tendency to avoid conflict get women into some dangerous situations that could be prevented with just one little word: no.

If I could leave one gift to this world, it would be to help people be more comfortable with healthy confrontation and the confidence to question motives without feeling impolite about it.

How can our readers further follow your work online?

All my upcoming events and the latest topics that are living in my brain rent-free can be found at sam-chandler.com but I also love connecting and collaborating with folks on LinkedIn.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

About The Interviewer: Vanessa Ogle is a mom, entrepreneur, inventor, writer, and singer/songwriter. Vanessa’s talent in building world-class leadership teams focused on diversity, a culture of service, and innovation through inclusion allowed her to be one of the most acclaimed Latina CEO’s in the last 30 years. She collaborated with the world’s leading technology and content companies such as Netflix, Amazon, HBO, and Broadcom to bring innovative solutions to travelers and hotels around the world. Vanessa is the lead inventor on 120+ U.S. Patents. Accolades include: FAST 100, Entrepreneur 360 Best Companies, Inc. 500 and then another six times on the Inc. 5000. Vanessa was personally honored with Inc. 100 Female Founder’s Award, Ernst and Young’s Entrepreneur of the Year Award, and Enterprising Women of the Year among others. Vanessa now spends her time sharing stories to inspire and give hope through articles, speaking engagements and music. In her spare time she writes and plays music in the Amazon best selling new band HigherHill, teaches surfing clinics, trains dogs, and cheers on her children.

Please connect with Vanessa here on linkedin and subscribe to her newsletter Unplugged as well as follow her on Substack, Instagram, Facebook, and X and of course on her website VanessaOgle.