Over the course of his career, Alex Santangelo has learned that being a strong leader isn’t about driving success — it’s about creating the right conditions for it to manifest.
That’s why he aims to remove obstacles, foster collaboration and ensure everyone on his team understands the value they bring to the table in his role as sales director at Klaviyo. Santangelo said he has seen his fair share of great — and not so great — leaders throughout his career, and after analyzing their behaviors and decisions, he has learned how to effectively help others excel.
Honesty is key to his leadership philosophy, reflected in the ways he communicates ideas and information with his team and how he shows up to work each day.
“This openness builds a culture where people feel safe to contribute boldly, challenge ideas constructively, and grow beyond their own expectations,” Santangelo said.
When team members feel valued, supported and driven by a sense of purpose, they consistently achieve extraordinary results, which is why leaders like himself must strive to ensure people have the right resources and support they need to work as a team.
Outbound Business Development Manager Taylor Chinitz embodies a similar leadership style, guided by the idea that employees deliver their best work when they feel seen, supported and trusted rather than micromanaged.
“That’s why I lead with empathy, curiosity and a deep commitment to helping each rep grow in the direction they want, whether that’s within sales or beyond it,” she explained.
Chinitz said that “culture is everything” when it comes to driving success, which is why she makes an effort to create a team environment in which people speak up, make mistakes and learn out loud.
“I want my team to feel connected to each other, to our broader company initiatives and to the work, so we build shared rituals, collaborate constantly, and always make room for a little fun along the way,” she said.
For Santangelo and Chinitz, being a leader isn’t about standing at the helm; it’s about giving others the chance to steer while providing them with the opportunities and support needed to help them reach their goals — and those of the business as a whole.
Below, both leaders outline the key pillars that define their leadership philosophies, offering insight into what it’s like to work on their teams at Klaviyo.
About Klaviyo
Klaviyo aims to make it easier for business-to-consumer brands to understand their customers and grow more quickly. The company’s platform combines marketing automation, analytics and customer service to enable B2C brands to deliver personalized, real-time customer experiences.
1. Set a High Bar
“Sales is a metrics-driven role and is defined by our ability to not only achieve but exceed our goals. Naturally, this starts with quota, but my greatest impact can be felt in pushing my team to exceed in areas beyond quota. For example, pipeline is the fuel that feeds our team. If we set too low of a bar, it will ultimately impact our ability to achieve our quota. I focus on compartmentalizing the role, setting clear and achievable expectations and holding the team accountable to them. But the best leaders go further; they see potential in people that they may not yet see in themselves and push them to reach it. By raising the standard, providing the right support, and challenging individuals to grow, we create a culture where exceeding expectations becomes the norm.”
2. Have a Team-First Mindset
“My firm belief is that a leader’s primary responsibility is to ensure the success of their team. While I may have my own number to hit, that is secondary to the overall performance of my team. My success as a leader is tied to my team’s success and this is manifested in things like quota attainment, time to ramp, the number of promotions, etcetera. When my team is thriving, I thrive.”
3. Cultivate an Environment of Coaching and Enablement
“A commitment that I make to my team and hold myself accountable to is that you will be a better version of your ‘sales self’ when you leave my team. I uphold this commitment through a consistent focus on training, coaching and development work. This includes segment-wide sessions on core topics, manager enablement to support their own team, and one-on-one coaching. We take a long-term mindset to build the skills to drive long-term overachievement, at times to the slight detriment of the short term. This focus helps develop a sustainable structure for long-term performance and growth.”
4. Provide Transparency and Clarity
“I believe in providing absolute clarity, defining exactly what ‘good’ looks like and ensuring every goal is connected to the broader company mission. When changes occur, I communicate the full context behind the decision, highlighting both the pros and cons, and most importantly, outlining a clear plan for how we move forward and the results we expect to see. I view transparency not as a one-time communication but as an ongoing commitment to keeping the team informed, aligned and focused. This means setting explicit expectations so there is no ambiguity about targets, priorities or the path to achieving them. By pairing clear direction with open communication, I create an environment where every individual understands how their work contributes to our success, ensuring we are united in both purpose and execution every day.”
“By pairing clear direction with open communication, I create an environment where every individual understands how their work contributes to our success, ensuring we are united in both purpose and execution every day.”
5. Be Vulnerable
“I endeavor to bring my true authentic self to work every day. I lead with vulnerability, recognizing that I don’t always have every answer, and at times, I am wrong. I work to understand my gaps or blind spots and make an effort to fill those so that I can be the best version of myself that I can be. This authenticity creates a safer and more comfortable environment for my team to bring their own selves to work as well. When people can bring their whole selves to work, they are more engaged, collaborative and innovative. This type of supportive and encouraging culture not only strengthens relationships within the team but also makes coming to work something to look forward to. That positivity, in turn, fuels performance and creates a cycle of continued success, where both individuals and the team as a whole are motivated to excel and grow together.”
6. Find Opportunities for Collaboration
“While each team member has their own individual number to hit, I believe strongly that sales is a team sport. We are in this together — facing similar challenges, overcoming the same objections and striving toward shared goals. While the path to success can vary for each individual, collaboration ensures we find the best possible solutions, whether it’s strategizing on a deal, developing a new approach or solving an operational challenge. By fostering a culture where team members actively share ideas, insights and best practices, we leverage the strengths of the collective to elevate performance across the board. This collaborative mindset not only improves results but also builds stronger relationships and mutual trust. When we work together, we amplify each other’s strengths, fill in gaps, and create an environment where the whole team can achieve at the highest level. Ultimately, our shared success becomes greater than the sum of individual achievements.”
1. Lead With Empathy and Curiosity
“I make it a priority to truly understand each team member; not just their work, but what motivates them, their strengths, challenges and long-term goals. This means asking thoughtful questions, listening actively, and tailoring my coaching and support to fit each person’s unique needs. Approaching leadership with empathy helps build trust and openness, which creates a stronger connection and better collaboration. Curiosity keeps me from making assumptions and encourages continuous learning not just for my team but for myself as a leader. I believe when people feel genuinely seen and understood, they’re more engaged, confident and willing to push themselves, which drives overall team success.”
2. Tailor Coaching to the Individual
“I believe there’s no one-size-fits-all approach to coaching. Every rep comes with different experiences, strengths and growth areas, so I focus on meeting them where they are. I use data and metrics closely to identify specific coaching opportunities, whether it’s activity levels or conversion rates, to pinpoint where someone might need extra support or skill-building. For those who are excelling, I look for ways to challenge and stretch them with new projects, mentorship roles or leadership opportunities. By customizing coaching based on both qualitative insight and hard data, I help each rep build confidence and skills in a way that feels meaningful to them, which leads to stronger performance and deeper engagement.”
3. Psychological Safety Encourages Risk-Taking and Learning
“I prioritize building an environment where my team feels safe to speak up, share ideas, and take risks without fear of judgment or punishment. Mistakes are framed as learning opportunities, not failures, which encourages experimentation and growth. When business development representatives know their voices matter and won’t be dismissed, they’re more likely to openly share challenges they’re facing, collaborate on solutions and try new approaches to engage prospects, leading to faster problem-solving and better pipeline outcomes. This sense of safety leads to stronger trust, better communication and ultimately higher performance across the team.”
“Mistakes are framed as learning opportunities, not failures, which encourages experimentation and growth.”
4. Promote Team Culture and Shared Goals
“I believe a tight-knit, collaborative team culture is essential to success. I work to create a space where everyone feels bought into our shared mission and goals not just individually but as a collective. This means encouraging teammates to support each other, share knowledge, and celebrate wins together. We build rituals like presenting on weekly wins, sharing each time a meeting is booked and how in our team Slack channel, or starting meetings with fun ice breakers that help everyone connect on a personal level and keep morale high. When the team feels connected and aligned, motivation and productivity naturally follow.”
5. Make Work Fun
“I firmly believe that enjoying the workday matters just as much as hitting our numbers. I prioritize creating moments of joy and connection, whether that’s kicking off team meetings with silly ice breakers, celebrating wins big and small, or organizing fun team outings. We’ve played pickleball, gone to arcades, had team dinners and even visited dart bars. These experiences build camaraderie and help the team decompress, which boosts energy and resilience. When people enjoy the journey, they stay motivated and engaged, and the results speak for themselves.”
