Issue #49: 15 Customer Success Leaders Share Their Best Career Advice

To wrap up Women’s History Month, we’re highlighting the best career advice from the incredible women driving Customer Success. They offer unique and powerful lessons about focusing on what matters, advocating for yourself, building a strong network, and more. 

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Mary Poppen, CCO of Glint at LinkedIn

While reflecting on lessons learned throughout my career in Customer Success and Experience, five key principles came to mind (not necessarily in priority order):

1. Put the customer at the center of all decisions: If decisions are made with what is in the best interest of your customers, business results will follow, including increased revenue as well as enhanced employee engagement. 
2. You can be kind and successful at the same time: Having empathy and compassion for employees and customers goes a long way in fostering engagement and loyalty.
3. Stay curious! You don't know what you don't know. Your career is a journey of unending learning opportunities. Keep an open mind and look for ways to continually improve.
4. Focus on customer intimacy as the primary outcome: Understand your customers better than anyone else. Know what they need, when they need it, and deliver it in a way that’s best for them—before they even know they need it! This is the key to personalization and differentiation and it’s the foundation of a long-lasting, trusted partnership.
5. Lead, don’t follow: Continuously innovate and look for improvements in the customer experience. Just because things are working and results are strong doesn't mean they can't get even better!

Cairo Amani, CX Lead at Cutback Coach and Co-Founder of ThriveNetwork

Build a strong professional brand. Be able to speak confidently to who you are and what you bring to the table. When you walk into a room, no one should get the chance to tell your story except you.

Gemma Cipriani-Espineira, VP Customer Success at Chili Piper

Gloria Steinem said, “The truth will set you free, but first it will piss you off.” The truths I have learned in my career are that: 1) people are unpredictable, 2) systems can be unfair, and 3) top performers don’t like having a “boss.” Acknowledge these hurdles and choose to focus your energy on driving results.

Georgia Harrison, Senior Director of Customer Success EMEA at Braze

1. In Customer Success, learn the product under the hood. You’ll be credible with more stakeholders and move more efficiently through your customer tasks.
2. For women in Customer Success, ask for a promotion every time you’re eligible to practice the skill of representing yourself. Agree on this principle early on with your manager—after all it can help them explain areas where you need to grow to get that promotion.
3. As you transition from a CSM to a CS leader, don’t hold on to accounts for too long. It can feel like a safe zone in new water, but the longer you spend there, the shorter the runway you give yourself to set up for a future VP role.

Anita Toth, Churn Consultant

Follow your heart, despite your head and everyone else telling you that it isn't the right path. I've taken jobs that were lower pay, less stable, and harder work because I knew in my heart that ultimately those jobs would bring me to the place I wanted to be in my career. It was hard tuning out the strong voice of my inner head and the external voices of my friends and family. But in the end it worked out far better than if I had gone against what my heart wanted. The career path we take isn't always easy, but you truly do know what's best for you—because your heart tells you.

Emily Garza, AVP of Customer Success at Fastly

1. Create your own Board of Directors. Throughout your career you hit sticking points where you'll need advice or someone to brainstorm with. Similar to a corporate Board that is maximized for diverse experiences, you want to create relationships with people of different backgrounds to leverage depending on the challenge you face. Maintaining this network (especially when you don't “need them”) is critical. 
2. Be clear on your goals. In setting a goal, communicate it to create awareness, gather feedback, and be held accountable. Set milestones so you can see progress and wins as well as checkpoints for feedback to understand if you are on the right path. If there isn't a clear path, sit down with your manager (or on a broader scale, with people in your personal Board of Directors) and create a plan. 
3. Be able to tell your value story. Advocating for yourself can be uncomfortable at first, but it is critical for career growth. Determine how you feel most authentic in sharing wins and successes—your manager doesn't see everything! Be able to articulate your own personal elevator pitch, reflecting on your key “superpowers,” and how they benefit the role, project, etc. 

Lauren Costella, VP of Customer Success at GoodTime.io

Never be ashamed to fully understand. This advice came from my mentor Jeanine Moss earlier in my career when I worked in Strategic Communications at the Pentagon. People would use jargon and language I didn't understand, and I felt, fairly or not, pressure that I was supposed to know what everyone was talking about to be good at my job, even though I had never been exposed to much of what they were saying. And by golly, sometimes people used so much fluff that what they said didn't have meaning or substance!

She encouraged me to keep asking questions, to keep digging until things were clear or broken down in a way I could understand. I use that technique in both my personal and professional life because communication and, more importantly, understanding between people - customer, client, teammate, colleague, boss, family, or friends - remains critical for any kind of business and/or personal success.

Kim Oslob, Senior Director of Customer Engagement at MeasuringU

Every company and every Customer Success role is different. Align with a strong mentor who has worked in a variety of different situations and can help you in your career. When you have grown in your career, become a mentor to help others grow strong. 

Teresa Anania, VP of Global Customer Success and Renewals at Zendesk

1. Build a network internally and externally. Learning from peers will accelerate your growth immensely plus enable you to nurture relationships that will be invaluable in your career.
2. Be resilient. Model how to have courageous and difficult conversations and how to "lean in." Have a strong point of view grounded in data (know your data). Expect to be "equal" with stellar performance, but don't make gender your issue.
3. Balance work and family. Prioritize what matters most to your kids (e.g. making cookies at 3 a.m. for a bake sale the kids knew nothing about isn't where I focused my volunteer time). You can have it all, but you have to self-manage to make it work.

Katrina Coakley, Director of Customer Success at talentReef

To anyone new in Customer Success, track your major wins, your losses, and trust yourself. There will be times when you may not take the next right step. Tracking your wins will help to provide clarity on all the times you get it right. Tracking your losses is meaningful as long as you learn from the experience. And trust yourself because no one at the company knows more about your customers than you do.

To Customer Success leaders, write down your “why.” You took on the role for a reason. Determine your priorities and put leadership battles that fall outside of those areas in the parking lot. Spend time with the CSMs you are privileged to lead. And set healthy boundaries for yourself—this includes setting aside time for an activity that you enjoy purely because you enjoy it.

Shirley Chapman, Senior Director of Customer Success Management (EMEA) at Pluralsight

Don’t count yourself out before exploring the possibilities. There is nothing to lose in expressing an interest, even if you think it’s a "not now but later" opportunity. I got my first leadership role because I applied for a position I didn't think I would get, but wanted to experience the process! Ask for feedback and advice from a range of people, inside and outside the company to get different perspectives. Believe in yourself and always bring your best self forward.

Kelly Berg, VP of Customer Success and Solutions at Ambition

Focus on timing. Was it the right time to move across the country for an opportunity or take a risk to join a startup? Was it the right time to ask for more responsibility? Or was it the right time to stick with something through a challenge and come out on the other side? That advice has helped me stay dialed in on maintaining balance between big career moves and my other key values—my family, where I want to live, and what I want each day to look like.

Maranda Dziekonski, SVP of Customer Success and People at Swiftly

I've received a lot of advice over the years, but a few points that have always stuck with me are:

• Approach all conflicts with curiosity.
• Ask for help often.
• Never be afraid to admit what you don't know.

I've always carried these with me, and while I am less than perfect, on occasion, I use them to ground me!

Monica Trivedi, Director of Global Customer Success at Schneider Electric

My best career advice centers around four pillars that have guided me for most of my professional and personal journey: 1) be authentic, 2) challenge the status quo, 3) advocate for what you deserve, and 4) embrace uncertainty.

Shadavia Jones, Scaling Customer Success Team Manager at HubSpot

To build your personal brand within a company, become the expert at something. It is not enough to just be great at your job function. People need to think of you and your skillset when opportunities arise, even if it's unrelated to your role. Find your thing, your foundation that you can build any career on, then reflect on the question, "Am I a good employee, or am I an expert?"

Negotiation is one of the most underrated skills. You're always negotiating on the job—with your clients, your worth when evaluating a new job offer or raise, and especially when you're trying to gain additional experience via strategic projects, so it helps if you're good at it. Negotiation is a muscle that strengthens over time, so start small but be sure to use it frequently.

The Customer Success mantra is typically some version of "put the customer first." My edited version of this is, "put humans first" — yourself included. You won't be able to delight customers if you aren't feeling like your best and most productive self. Do what's best for your customer by showing up as your authentic, well-rested, and energized self—the human in your customer depends on it.

No matter what line of business or role you're in, remember you're in the people business first. People are the foundation for all that you want to achieve over your career. Connect, empathize, and show compassion for them. 

This week's top posts

INDUSTRY

The Missing Piece of Software Sales

Here’s Rav Dhaliwal with a call to end the dated sales orthodoxy mindset of considering a sale complete at contract signature. He makes the case that Customer Success teams are still in a reactive state because they are “focused on solving the problems of a legacy perpetual license sales motion” instead of being able to drive the “continuous sales” cycle. 

Read the full post

COACHING

Change Management in Customer Success

Being able to influence changes in behavior is at the core of the role of a CSM. This article articulates what “change management” includes and shares some scenarios of what it looks like in practice. Consider sharing this article with the team, and continue to reinforce this approach through coaching. 

Read the full post

VIRTUAL DISCUSSION

Lessons From Running CS Ops at Zoom, Gainsight, Stack Overflow, & More 

On April 22, we’re hosting a live panel discussion on everything CS Ops related. Sign up, submit your questions early, and share the link with your colleagues. (If you can’t attend live, you can still register and get the recording afterwards.)

Reserve your seat

Success Happy Hour is a weekly newsletter for Customer Success leaders. Each week we feature one digestible piece of advice or a framework from a top Success leader, along with the best resources from that week. Subscribe here.