Leading with Transparency & Vulnerability by Dave Sherry, Gong

Senior Sales Manager, Mid-Market & Commercial at Gong, Dave Sherry sat down with us to discuss how he influences high performance & motivation, his biggest learnings and failures as a leader, and how to create a diverse, inclusive culture.

With 11 years of experience working for AdRoll, Amplitude, and now leading the Mid-Market & Commercial team at Gong, Dave is an emotionally intelligent leader, who has good judgment, drive, and leads with transparency, and vulnerability.

Influencing high performance & motivation

“In today’s challenging market conditions, which extend beyond just the tech sector, it’s easy for us all to feel overwhelmed—especially with the media constantly highlighting issues like the housing crisis, the rising cost of living etc.

My core belief in creating a high-performing team is to first foster an environment at Gong that not only gives people a break from these external pressures, but a place they want to be part of. The environment needs to be fun and energetic but also encourages vulnerability. This is foundational for establishing clear, aspirational, and team-based goals and objectives people aspire to achieve.

A key part of this process involves understanding each team member’s motivation and connecting that to our collective objectives. I draw this inspiration from Daniel Coyle’s "Culture Code," and this approach has consistently shown positive results for us, quarter after quarter.”

To be a great leader, you must have a why, a purpose, something that drives you to get up every day and inspire others around you. Dave’s why is two-fold; “1. is my wife & kids. I want my children to get the same opportunities I did growing up, and I want them to hold me in the same esteem as I did with my parents growing up. 2. I want to be the person at the top of the pile such as the CRO/CEO. I have strong ambitions to feel the challenges, the sense of progress, the achievement, and the pride that comes with the territory of this role.”

When speaking with Dave, it was clear he was not only purpose-driven but emphasised the importance of having your own values, instead of just leaning on your companies’. Here is what Dave said are the core values he lives by:

We’re not saving lives - enjoy the process & be grateful. Pressure is a privilege.

Assume good intent in others.

Act now, worry later. Pace is everything.

Share a lot.

Creating an inclusive team, and allowing them to bring their full selves to work

Wiser Elite’s mission is to change the way people think about sales. We want to change the stereotype of sales being a white, male-dominated industry. You wouldn't have 11 defenders on a football team, so why have people in your team who are all from similar backgrounds, with similar experiences and views on the world?

“I work to ensure our team is diverse and unified, allowing everyone to thrive and contribute their best selves.”

It’s clear that Dave and the team at Gong align with our mission, and here is how he does it:

“Creating a Culture of Belonging:

In our weekly team meetings, I focus on building a culture where storytelling and openness are encouraged. I start by sharing what’s happened in my life over the past weekend —both the good and the challenging—along with what’s on my mind and what I’m excited about. The rest of the team is then encouraged to do the same, allowing us to share stories & perspectives in a safe space where everyone’s voice is valued. Mostly, it turns into a healthy amount of deep belly laughs which can only be a good thing.

Weekly 1:1s:

I hold weekly one-on-one check-ins with each team member to understand their individual needs, progress toward their goals, and overall feelings about their work experience. This regular communication helps me better support them, tailor their work experience, and build stronger relationships with each team member.

Celebrating Differences:

I celebrate our diversity by highlighting & showcasing the different backgrounds, hobbies, and experiences across the team. Whether someone has a passion for cooking, or someone is competing at an elite level in showjumping for example, I want to ensure each person’s thing is given the time & space to be highlighted & celebrated. These activities not only strengthen our connections but also enhance our team’s creativity in different ways.”

Lessons in leadership

As we all know, things don’t always go the way you planned, especially when leading a team. Failure is a byproduct of success, and unless we are aware of those mistakes, we will struggle to develop and move forward as not only a leader but an individual.

Dave shared a mistake he has made in his career, and what it taught him:

“One standout experience was transitioning from SDR management to AE management. Initially, I jumped into deals, wanting to be the hero, but I realised this was counterproductive. The real focus should have been on listening to my team, recognising their strengths, and coaching them to reach their desired outcomes independently. This shift not only improved my leadership skills but also strengthened our team collaboration.

A key lesson I've learned in leadership is the importance of managing expectations to avoid overpromising and underdelivering. Early on, I tried to solve every issue myself, but I’ve since learned the value of saying no and delegating effectively. Empowering my team to take ownership of their results has proven to be more productive for everyone.”

And whilst reflecting on mistakes is crucial for learning, we need to look back on what went well, and celebrate those successes.

“The standout highlight for me as a leader is when I’m actively supporting new reps on the team to land their first deal. It's such a rewarding milestone, and I know firsthand how fulfilling it is for them.

I also take great pride in seeing seasoned reps on my team reach their goals, whether that means earning a promotion, making it to President’s Club, or saving enough to make a significant purchase, like buying a home. It's inspiring & incredibly fulfilling to witness their achievements.”

Leadership isn’t for everyone, and some will have a hugely successful career staying as an IC. Often people think leadership is the only next step for progression, which has hindered so many people’s careers, as they don’t possess the skills to be an effective leader. Knowing which route is right for you, and not rushing into leadership before you’re ready is crucial. We wanted to understand why Dave took the step and the skills he possesses to make him right for the job.

“It might sound cliché, but sports have had a significant impact on my life, and I see strong parallels between being part of a sports team and working in a performance-driven environment like sales. I've always been more drawn to the leaders and captains of teams, rather than the teams themselves. Their charisma, sense of accountability, and ability to unite top talent to achieve great results really resonate with me. Figures like Sir Alex Ferguson, Jose Mourinho, Michael Jordan, Phil Jackson, and Graham Henry inspire me.

I've also experienced firsthand how a great leader can make a huge difference, while a poor manager can be really discouraging, especially for newer reps like SDRs and entry-level reps. I believe the SDR team is the backbone of the go-to-market organisation, nurturing the company’s future top sales reps, sales engineers, and customer success managers. If a leader effectively coaches these reps, sets clear expectations, and removes obstacles, the company’s future looks promising.

In terms of what I bring to leadership, I believe I possess strengths like emotional intelligence, good judgment, drive, transparency, and vulnerability. I know I’m not the smartest person in the room - and I don’t need to be - but I do excel at bringing people together and motivating them around a common goal, all while having fun along the way.”

Why Gong?

“I chose to work at Gong for three primary reasons:

The Product:

The bulk of my SaaS experience before joining Gong was selling & leading teams targeting Product & Eng personas. I wanted to experience selling a product to GTM leaders like myself, and I saw that Gong was doing something different & exciting for folks on the revenue side of the house - from ICs right up to CROs. Having had prior experience both using & recommending Gong, I knew early on that it was an incredible product that provided so much info more than any CRM could, with an unrivaled velocity for shipping new features & capabilities. The use cases were & still are endless.

The People:

Before joining, I had always been intrigued by how passionately vocal Gong employees were on LinkedIn. I was borderline suspicious of whether or not bots were posting on behalf of employees, promoting the Gong message like it was a testament, but then I met a few “Gongsters” and it made sense. They were welcoming, curious, direct, energetic & laser-focused on acting - operating principles that were felt throughout my interview process and still hold today 3 years later.

The Potential:

The SaaS ecosystem for revenue teams was & arguably still is dominated by CRMs like Salesforce, Hubspot & Microsoft Dynamics. With Gong’s ability to capture, deeply understand and deliver customer interactions to GTM leaders, I felt the platform could offer companies more insights to successfully executive GTM initiatives and grow revenue efficiently. Furthermore, the company’s double-digit annual growth, and headcount plans for Europe, made Gong’s future very appealing for me.

Today, Gong is all about transforming and empowering revenue teams by leveraging customer interactions to boost business efficiency, improve decision-making, and drive revenue growth. Our Revenue Intelligence platform uses cutting-edge AI technology to help teams capture and understand every customer interaction—all in one integrated space.

Gong’s AI platform encompasses conversation intelligence, sales forecasting, and prospecting/engagement. Our 4000+ customers benefit from:

Improved Productivity: Automate workflows and eliminate manual tasks, freeing teams to focus on high-value activities that drive revenue outcomes.

Increased Predictability: Leverage AI-driven insights to improve forecasting accuracy and gain real-time visibility into pipeline health and deal progression.

Revenue Growth: Scale faster by aligning teams around data-backed strategies that maximize win rates, expand customer relationships, and drive revenue growth.”

If you have enjoyed this piece and would like to learn more about Gong, then please visit their website here, or get in touch with Dave Sherry.