Refuse to Lose: 5 Ways Freshworks CMO Stacey Epstein is Driving Change

As an experienced CEO and tech entrepreneur, I've seen firsthand the importance of leadership, especially in tough times.

It was a rewarding experience when we had the privilege of hearing from Stacey Epstein, Chief Marketing Officer of Freshworks, during our leadership day at the recent company-wide G2 Mid-Year Meetup.

A member of our newly formed Executive Advisory Board and a recognized 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 world.

During her session with us, she shared her perspective on driving change, which resonated deeply with our G2 leadership group. Here are key lessons learned from Stacey's decades of experience.

1. Maintain a “refuse to lose” mentality

Stacey, a former college football player, compared business to sports, using NBA phenom Steph Curry as a poignant example. Despite his relatively small height (1.70m) in high school, Curry refused to take on a loser mentality – an approach Stacey took in his role as CEO.

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

Her company was successful in its acquisition, which she attributes to her persistence and that of her management team in weathering the storm no matter how long it took.

2. Remember that business and economic cycles are temporary

Stacey and I share the scars of economic recessions. She advises to remember that these cycles are temporary and encourages communicating this perspective to teams, which is essential to avoid morale degradation in the face of challenges.

Highlighting the cyclical nature of business, Stacey shared an example of working as a salesperson earlier in her career. Although she landed an amazing deal that she worked hard on, the following quarter she didn't have enough pipeline and wondered how she was going to make her numbers.

Rather than getting bogged down in short-term difficulties and the temporary nature of business and economic cycles, it focuses on the long-term 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 barriers for them

In difficult times, understanding your team's personal motivations becomes more crucial than ever. Stacey emphasizes taking a hands-on approach, where leaders actively work to understand and remove the obstacles their teams face, rather than simply dictating orders.

It creates a unified and motivated team, even in the most difficult circumstances. Even if the team doesn't immediately win, they will bring them together to feel and know that they are all part of the same mission.

4. Prioritize sustainable growth over short-term indicators

In the midst of the daily chaos and growing list of deliverables, it's easy to lose sight of the ultimate goal: to build a profitable and sustainably growing business. Stacey believes in elevating this principle as the North Star that aligns the whole team.

Achieving these long-term goals can only happen when teams are aligned to effective goals through OKRs and role/responsibility drills.

5. Let go of negative emotions and take action to solve problems

Stacey practices letting go of negative emotions and quickly shifts into problem-solving mode. Whether it's a rejuvenating ride or a strategic pivot in the business, action is his remedy for the paralysis that negativity can cause.

When faced with problems, she is not one to linger. She is ready to find solutions, a lesson she actively passes on to her team. Stacey's advice to exercise to help negative emotions pass and go into problem-solving mode touches me deeply.

To be a conscious leader, I set aside an hour each day for an outdoor activity that I enjoy: running, biking, hiking, or going to the gym. I always feel lucid and full of energy when I return.

Focus on the long term

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

Reflecting on Stacey's lessons, the main message I have for our G2 team and other business leaders

Refuse to Lose: 5 Ways Freshworks CMO Stacey Epstein is Driving Change

As an experienced CEO and tech entrepreneur, I've seen firsthand the importance of leadership, especially in tough times.

It was a rewarding experience when we had the privilege of hearing from Stacey Epstein, Chief Marketing Officer of Freshworks, during our leadership day at the recent company-wide G2 Mid-Year Meetup.

A member of our newly formed Executive Advisory Board and a recognized 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 world.

During her session with us, she shared her perspective on driving change, which resonated deeply with our G2 leadership group. Here are key lessons learned from Stacey's decades of experience.

1. Maintain a “refuse to lose” mentality

Stacey, a former college football player, compared business to sports, using NBA phenom Steph Curry as a poignant example. Despite his relatively small height (1.70m) in high school, Curry refused to take on a loser mentality – an approach Stacey took in his role as CEO.

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

Her company was successful in its acquisition, which she attributes to her persistence and that of her management team in weathering the storm no matter how long it took.

2. Remember that business and economic cycles are temporary

Stacey and I share the scars of economic recessions. She advises to remember that these cycles are temporary and encourages communicating this perspective to teams, which is essential to avoid morale degradation in the face of challenges.

Highlighting the cyclical nature of business, Stacey shared an example of working as a salesperson earlier in her career. Although she landed an amazing deal that she worked hard on, the following quarter she didn't have enough pipeline and wondered how she was going to make her numbers.

Rather than getting bogged down in short-term difficulties and the temporary nature of business and economic cycles, it focuses on the long-term 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 barriers for them

In difficult times, understanding your team's personal motivations becomes more crucial than ever. Stacey emphasizes taking a hands-on approach, where leaders actively work to understand and remove the obstacles their teams face, rather than simply dictating orders.

It creates a unified and motivated team, even in the most difficult circumstances. Even if the team doesn't immediately win, they will bring them together to feel and know that they are all part of the same mission.

4. Prioritize sustainable growth over short-term indicators

In the midst of the daily chaos and growing list of deliverables, it's easy to lose sight of the ultimate goal: to build a profitable and sustainably growing business. Stacey believes in elevating this principle as the North Star that aligns the whole team.

Achieving these long-term goals can only happen when teams are aligned to effective goals through OKRs and role/responsibility drills.

5. Let go of negative emotions and take action to solve problems

Stacey practices letting go of negative emotions and quickly shifts into problem-solving mode. Whether it's a rejuvenating ride or a strategic pivot in the business, action is his remedy for the paralysis that negativity can cause.

When faced with problems, she is not one to linger. She is ready to find solutions, a lesson she actively passes on to her team. Stacey's advice to exercise to help negative emotions pass and go into problem-solving mode touches me deeply.

To be a conscious leader, I set aside an hour each day for an outdoor activity that I enjoy: running, biking, hiking, or going to the gym. I always feel lucid and full of energy when I return.

Focus on the long term

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

Reflecting on Stacey's lessons, the main message I have for our G2 team and other business leaders

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