“I can’t keep doing this,” the harried customer success executive confided during their first meeting with the consultant. As a Director of Customer Success, managing a team of ten, she was drowning in work and drastically underpaid. Her eyes told the story of countless late nights and missed family dinners. What happened next, the process of moving from overwhelmed to empowered, would transform not just her career, but her entire approach to leadership.
In the coaching sessions, the focus was on three key areas: strategic leadership, organizational design, and executive presence. Like an oak tree growing stronger with each passing season, she developed deep roots in her leadership philosophy while reaching higher in her aspirations.
The results came faster than either of us expected. Within six months, she earned her first VP promotion, and her team doubled to twenty passionate CS professionals. By the time she completed her tenure, she was leading three directors and a thriving organization of forty team members.
But the real breakthrough came with her next move. Armed with confidence and clarity about her value, we negotiated a compensation package that placed her among the top-paid VPs of Customer Success in the industry. In her new role, she didn’t just manage an organization – she transformed it. While she put in the hard work every single day, she often reflected that having a coach who had walked this path before accelerated her journey exponentially. “Having someone who could see both the pitfalls and opportunities ahead of me,” she says, “made all the difference between gradual progress and transformational change.”
I remember one pivotal coaching session where my client’s voice cracked with exhaustion over our video call. After years of pouring everything into her role, she’d hit that dangerous precipice where burnout wasn’t just looming – it was actively pulling her under. Her usually sharp focus had given way to a distant stare, and her typical strategic questions were replaced with something that stopped me in my tracks: “Maybe I’ll just go get a job at Lowe’s or Home Depot,” she said with a hollow laugh. “Organizing paint swatches and helping people pick out light fixtures sounds really nice right about now.” The weight of her words hung heavy in our virtual space. This wasn’t just ordinary stress speaking – this was a seasoned executive who’d lost sight of her own worth amid the chaos. The pressure she’d been putting on herself had compressed her vision so tightly that she could barely see beyond the next crisis, let alone the next week.
As she continued, years of pent-up frustration spilled out in a torrent of words and emotions. Each challenge she described painted a picture of accumulated battle scars: the 11 PM emergency calls from her CEO, the resignation email from a key team member that landed in her inbox on a Sunday, and the churn notices that felt like personal failures. In our previous sessions, she mentioned these issues with professional detachment. Now, they emerged raw and unfiltered.
Instead of jumping in with solutions, I let the silence hold space for her truth. When she finally paused, I shared an observation that seemed to shift something fundamental in her perspective: “Leadership isn’t about avoiding problems – it’s about knowing with absolute certainty that they’ll appear on your desk every single day. The real power comes not from preventing the inevitable, but from approaching each challenge with a confidence that transcends the specific situation.”
I watched her expression change through my screen as this landed. The idea that she didn’t need to prevent every crisis – that her value came from her ability to handle them skillfully – visibly lifted a weight from her shoulders. We weren’t just talking about survival anymore; we were talking about mastery.
“What makes a great leader isn’t having all the answers,” I continued, “it’s having the tools and confidence to find them, no matter what question life throws at you. Every problem that lands on your desk is an opportunity to demonstrate that mastery.”
My role as an executive coach isn’t to eliminate the challenges my clients face – it’s to help them build such a robust leadership toolkit that they can approach any situation with unwavering confidence, whether they’ve seen it before or not.
That day, watching her reconnect with her own capability and power, I saw the moment when this truth transformed from an intellectual concept into a lived experience.
The lesson? When you combine raw talent with experienced guidance, you don’t just climb the career ladder – you take the elevator to the top.
The Challenge: Provide Coaching to Move a CS Exec from Overwhelmed to Empowered
The Consultant: Nils Vinje – Glide Consulting
The Outcome: A New VP of Customer Success
Glide Consulting delivers creative solutions to customer success challenges. We partner with our clients to bring clarity and definition to each area of Glide’s 4 P’s framework – People, Purpose, Process, and Platform. Glide was founded and is led by Nils Vinje, Customer Success industry veteran and recognized thought leader.
- Consulting – Deliver predictability in customer renewals and expansions.
- Leadership Coaching – Take your leadership to the next level with a tailored coaching program designed just for you by an industry expert and certified coach.
- Training – Enable your team to build strategic relationships with your clients that are the key to your long-term success.
