Refusing to Lose: 5 Ways Freshworks CMO Stacey Epstein Leads Through Change

As an experienced tech CEO and entrepreneur, I have seen firsthand the importance of leadership, especially during challenging times.

It was an enlightening experience when we had the privilege to hear from Freshworks CMO, Stacey Epstein, during our Leadership Day of G2’s recent company-wide Midyear Meetup. 

A member of our newly formed Executive Advisory Board and an acclaimed enterprise software veteran who has helped build many iconic SaaS brands – including SAP SuccessFactors, ServiceMax, and now Freshworks – Stacey is no stranger to the stormy weather of business.

During her session with us, she shared her perspective on leading through change, which resonated deeply with our group of G2 leaders. Here are the distilled key lessons from Stacey's decades of experience.

1. Maintain a "refusing to lose" mentality

Stacey, a former collegiate soccer player, compared business to sports, using NBA phenom Steph Curry as a poignant example. Despite his relatively small 5’6” stature in high school, Curry refused to adopt a losing mentality – an approach that Stacey adopted in her role as a CEO.

She had been in what she called a dire situation: facing problem after problem, when nothing was going right. But she maintained that mentality of refusing to lose and found a path forward.

Her business reached the successful outcome of getting acquired, which she credits to the perseverance of herself and her leadership team – weathering the storm, no matter how long it would take.

2. Remember that economic and business cycles are temporary

Both Stacey and I share the battle scars of economic downturns. She advises that we must remember these cycles are temporary and encourages communicating this perspective to teams, which is critical for preventing morale decay when facing challenges.

Underscoring the cyclical nature of business, Stacey shared an example of working as a sales rep earlier in her career. Despite landing an amazing deal she worked hard on, the next quarter, she was back to not having enough pipeline and questioning how she would make her numbers.

Rather than getting mired in short-term difficulties and the temporary nature of economic and business cycles, she focuses on the long view that tough times will pass. Communicating this perspective to teams prevents morale from sinking when obstacles arise.

3. Empathize with your team and remove obstacles for them

In tough times, understanding your team’s personal motivations becomes more crucial than ever. Stacey emphasizes adopting a hands-on approach, where leaders actively work to understand and remove the barriers their teams face, rather than just dictating orders.

This creates a unified, motivated team, even in the direst circumstances. Even if the team isn’t winning right then, it will band them together to feel and know they’re all part of the same mission.

4. Prioritize sustainable growth over short-term metrics

Amid the chaos of day-to-day and growing list of deliverables, it's easy to lose sight of the ultimate goal: building a profitable, sustainably growing business. Stacey believes in elevating this principle as the North Star that aligns the entire team.

Achieving those long-term goals can only occur when teams are aligned on efficient goals through OKRs and roles/responsibilities exercises.

5. Let negative emotions pass and take action to solve problems

Stacey practices letting negative emotions pass and swiftly shifts into problem-solving mode. Whether it’s through a rejuvenating hike or a strategic pivot in the business, action is her remedy for paralysis that negativity can induce.

When faced with problems, she’s not one to dwell. She's ready to find solutions, a lesson she actively imparts to her team. Stacey’s advice to embrace exercise to help negative emotions pass and shift into problem-solving mode resonates with me deeply.

To be a conscious leader, I block one hour each day for an outdoor activity that I enjoy – going for a run, bike ride, hike, or hitting the gym. I always feel clear-headed and energized when I return. 

Focusing on the long-term

Ultimately, Stacey's leadership style is a blend of hard-won wisdom, empathy, and unshakeable focus on the long-term vision. It is not just about surviving the challenges; it’s about leading a united and motivated team that thrives despite them. 

Reflecting on Stacey’s lessons, the main message I have for our team at G2 and other business leaders navigating tough times is this: It’s easy to be mired in today, where budgets are being cut and we’re not growing as much as we’d like. But as leaders, we have an opportunity to test our potential if we embrace a “refusing to lose” mentality, stay focused on the long-term vision, and see these difficulties as mere temporary phases.