At Applied Systems, sales development reps have had the opportunity to “score touchdowns and field goals,” all in effort to drive progress — and connect with each other.
The company’s sales team engaged in a football-themed contest called the “Two-Minute Drill,” where they competed against each other to hit sales targets.
“The competition boosted production, but more importantly, it sparked camaraderie,” Senior Sales Manager Julia Ysbrand said. “Reps were trading tips, coaching each other and celebrating teammates’ wins as if they were their own.”
This is just one of the ways in which she drives engagement on Applied Systems’ sales team, creating an environment that motivates reps to work hard and support each other along the way.
Meanwhile, at Monte Carlo, SDR Manager Devon Bridges fosters engagement through coaching. She tailors development to each rep’s motivations and goals, ensuring every rep has an equal chance to thrive.
“My coaching is direct, constructive and often in the moment, because growth happens fastest with real-time feedback,” Bridges said.
There are many ways for sales leaders to motivate team members, but for Jolene Ortiz, the most effective approach is consistent communication. As executive director of dealer sales and development at Edmunds, she recommends that sales leaders implement weekly team meetings in addition to other regular check-ins to ensure their direct reports have the chance to share their ideas and opinions.
“These regular check-ins are the perfect opportunity to set clear expectations, define monthly goals and track progress toward them,” Ortiz said.
Below, Ysbrand, Bridges and Ortiz share more about their leadership philosophies, how they keep reps engaged, and their advice for other sales leaders eager to motivate their own teams.
Applied Systems’ cloud-based software enables insurance agencies to develop online experiences.
Describe your leadership philosophy as it relates to employee engagement.
My leadership philosophy is built on the belief that iron sharpens iron. I don’t view myself as the person with all the answers; instead, my role is to create an environment where the team can challenge, support and learn from one another. Engagement starts with clarity; every team member should know exactly where we’re headed, what’s expected and how their work ties back to our larger goals. And most importantly, at the leadership level — consistency. Consistency in expectations, consistency in feedback and consistency in how you engage with your team.
“I don’t view myself as the person with all the answers; instead, my role is to create an environment where the team can challenge, support and learn from one another.”
Transparency tools like dashboards, leaderboards and visual progress gauges make performance visible and drive accountability. Just as importantly, engagement comes from recognition. Whether it’s a quick shout-out in Slack, spotlighting someone’s effort in a huddle or running a themed contest, consistent recognition ensures people feel seen and valued. When that happens, they bring energy, creativity and ownership to the work every day.
What types of resources — coaching, tools training, mentorship, etc. — does your team leverage to keep sellers engaged? How does this engagement directly impact their success and the success of the business?
We’ve built a rhythm of structured learning and reflection into the way we operate. Our team philosophy is, “Be better than you were yesterday.” Some of the ways we do that is collectively as a larger team. Our vice president holds regular skill development sessions where we tackle broader topics like, “asking for the business” or we have roundtable discussions about what’s working in prospecting efforts or strengthening our differentiation messaging.
For my team specifically, while we do things like deal reviews and strategy, we also lean into personal and professional development. We do this every other week, where team members rotate as presenters. They bring in a resource — a podcast, article or video — and lead a group discussion. What started as a simple book club has evolved into a broader professional and personal development forum that keeps the team curious and sharp.
In addition, we run quarterly business reviews, where we step back to evaluate performance, review pipeline health and set forward-looking strategies as a team. These sessions aren’t just about metrics; they’re about honest reflection and shared learning.
On the day-to-day side, I provide coaching in one-on-ones, and we use dashboards to keep performance transparent. We also run creative contests that make progress fun and visible. One recent example was a football-themed contest, the Two-Minute Drill, where reps “scored touchdowns and field goals” by hitting sales metrics. The competition boosted production, but more importantly, it sparked camaraderie. Reps were trading tips, coaching each other and celebrating teammates’ wins as if they were their own.
The impact of this engagement is clear: stronger pipelines, higher quota attainment and better close rates. But equally important is the cultural impact — a team that trusts one another, collaborates naturally, challenges each other constructively and shows up motivated every single day. That combination drives both individual success and long-term business results.
What advice would you offer to leaders in your field eager to drive greater engagement on their sales teams?
I’d say don’t overthink it. Engagement doesn’t come from one big program or initiative; it comes from the small, consistent things you do every day as a leader.
First, be clear. People want to know the “why” behind the goals, not just the numbers. When they understand how their work connects to the bigger picture, they feel more invested.
Second, recognize effort as much as outcomes. A deal might take months to close, but the behaviors that get you there — persistence, collaboration and creativity — deserve to be celebrated along the way.
Third, make engagement part of your team’s rhythm. That means connecting through daily huddles, one-on-ones or even quick Slack shout-outs. It doesn’t have to be complicated, but it should be constant.
And finally, don’t feel like you need to have all the answers. Some of the best engagement happens when the team learns from each other. Iron sharpens iron, so create opportunities for reps to share ideas, lead discussions and sharpen one another’s skills. When you do those things consistently, the numbers will follow. More importantly, you’ll build a team that takes real pride and ownership in the work.
Monte Carlo’s data and AI observability platform is designed to help enterprise teams reduce risks, improve data and AI health, and promote trust at scale.
Describe your leadership philosophy as it relates to employee engagement.
My leadership philosophy is built on clarity, empathy and empowerment. High-performing teams thrive when expectations are clear, coaching is consistent and every rep feels heard. I view the SDR role as a career launchpad, tailoring development plans to each rep’s motivations and goals. My coaching is direct, constructive and often in the moment, because growth happens fastest with real-time feedback.
Collaboration is critical; no one wins alone, so I create a culture of shared learning, call blitzes and cross-functional alignment. Curiosity is a superpower, so I push my team to challenge assumptions, share insights and keep learning. Above all, I lead with intentional energy and positivity. Engagement happens when reps know I have their back and future in mind, and that’s what earns me the right to push them to be their best.
“Curiosity is a superpower, so I push my team to challenge assumptions, share insights and keep learning.”
What types of resources — coaching, tools training, mentorship, etc. — does your team leverage to keep sellers engaged? How does this engagement directly impact their success and the success of the business?
Our team thrives because engagement is intentional, from the tools we use to the way we coach. We leverage platforms like Outreach and Nooks, whose live-call analytics and AI insights make coaching sharper and more impactful. Coaching is never one-size-fits-all. Onboarding builds a strong foundation, followed by real-time feedback, tailored coaching and peer-to-peer enablement.
Mentorship is key. SDRs are paired with account executives to learn how to think like full-cycle sellers, fostering ownership and proactivity. We also create space for reps to share expertise with one another, reinforcing a culture of continuous learning. Just as important, I customize growth paths based on each rep’s aspirations, giving them visibility into multiple career trajectories. The results speak for themselves: We’ve had nine SDR promotions in the last 16 to 18 months. This investment in engagement builds confidence, accelerates careers and fuels the pipeline that drives business growth.
What advice would you offer to leaders in your field eager to drive greater engagement on their sales teams?
Start by uncovering each rep’s “why.” Engagement is personal; what drives one seller may not matter to another. Take time to understand their goals and aspirations, then tailor coaching and development around them. This creates true buy-in and makes feedback more impactful.
From there, make clarity and accountability non-negotiable. Set clear expectations, but pair them with empathy and support so reps know you have their back. Build a culture of proactive ownership by coaching reps to run their pipeline like AEs and empowering them to diagnose their own success. Foster collaboration through peer learning and cross-functional alignment, because no one wins alone.
Finally, lead with intentional energy. Your tone sets the pace for the team, and positivity, resilience and belief are contagious. When reps feel seen, supported and challenged, they stay engaged, and when engagement is high, performance follows.
Edmunds’ marketplace enables consumers to shop for new and used vehicles, discover their vehicle’s value and read reviews to guide their car-purchasing decisions.
Describe your leadership philosophy as it relates to employee engagement.
A successful team is built on an understanding of what drives each individual within the group. As a leader, it is paramount to truly understand your employees; their motivations, aspirations and unique working styles. This knowledge enables me to provide resources that align with employee talents, empowering them to perform at their best and make meaningful contributions.
Effective communication and mutual trust are absolutely fundamental when providing feedback. Feedback should be a constructive dialogue, not a one-way street. When employees trust their leaders, they are more receptive to feedback, viewing it as an opportunity for growth rather than criticism. This transparent and respectful approach builds a stronger, more resilient team.
Recognizing accomplishments, both individual and collective, is crucial for fostering an inclusive and positive atmosphere. Celebrating successes, no matter how small, reinforces positive behaviors and demonstrates that every contribution is valued. An inclusive environment where every voice is heard and every contribution is recognized builds an engaged, motivated team committed to shared goals.
“Celebrating successes, no matter how small, reinforces positive behaviors and demonstrates that every contribution is valued.”
What types of resources — coaching, tools training, mentorship, etc. — does your team leverage to keep sellers engaged? How does this engagement directly impact their success and the success of the business?
Peer-to-peer mentorship is a powerful tool for building team synergy and success. I’ve found that individuals often learn most effectively from those who share similar experiences, challenges and successes. The synergy created through these shared journeys empowers team members to support, motivate and elevate each other toward collective and individual triumphs. We put this approach into practice by strategically transforming team meetings into interactive learning hubs.
We dedicate significant portions of these gatherings to success story sharing, where team members discuss their achievements and the strategies that led to them, providing tangible examples for others to emulate. We also create a safe space for open discussion on overcoming challenges, allowing peers to offer insights, alternative approaches and empathetic support. This collaborative problem-solving strengthens resilience and fosters a sense of shared purpose. Lastly, we use these meetings for focused training and open discussion on a specific topic, report or skill area. This hands-on, interactive learning is often more impactful than traditional top-down instruction.
What advice would you offer to leaders in your field eager to drive greater engagement on their sales teams?
Consistency is key to effective leadership, and it starts with consistent communication. By implementing weekly team meetings and monthly or bi-weekly one-on-one sessions, you ensure that your direct reports feel heard, which in turn fosters a culture of trust and transparency. These regular check-ins are the perfect opportunity to set clear expectations, define monthly goals and track progress toward them.
Beyond day-to-day work, it is essential to build a positive and supportive environment. This means celebrating achievements, no matter their scale, as every success contributes to the broader objectives. Recognizing these wins significantly boosts employee morale, cultivating an atmosphere that promotes team camaraderie and a collective determination to succeed.
Ultimately, a truly supportive leader leads by example. While you may not have all the answers, actively seeking solutions to remove obstacles is crucial. Always treat your employees with the same respect and consideration you expect to receive, setting a clear standard for how team members should interact with one another.
