Burnout on a sales team is no joke — and nearly nine out of 10 of sellers face it, according to a study by Gartner.
Sales teams face unique challenges that make them particularly prone to burnout. Challenging quotas and frequent rejection can take a toll on mental health, so it’s critical that salespeople have supportive team cultures to lean on during the peaks and valleys that are the nature of the job.
Built In found three Chicago sales teams that have amazing team cultures and put employees first.
MoLo Solutions is a third-party logistics provider that connects businesses with transportation to get products delivered.
Describe your sales team culture in one word. Why did you choose that word?
Intentional. Because nothing about our sales team is left to chance. Every decision, whether it is our tech stack, how we structure our teams, or how we onboard new sales representatives, is designed with purpose. Being intentional means we are not just chasing short-term wins; we are building a culture and strategy that supports long-term growth for our employees and our customers. Every decision we make is with clarity, care and impact in mind. This approach is what makes our work meaningful.
What are your team’s traditions or growth opportunities, and how do these traditions help team members connect, evolve and stay motivated?
One of our strongest traditions is a commitment to continuous development beyond just the onboarding phase. We are intentional about providing growth opportunities. These opportunities include skill-specific training, market education and career pathing for both individual contributors and aspiring leaders.
One example of our growth mindset in action is our Mock Madness tournament — a March Madness-style, single-elimination sales competition where every rep competes in mock scenarios. It is high-energy, skill-focused and designed to drive mastery through practice. Traditions like this keep our team sharp, connected and motivated. Growth isn’t just encouraged — it is part of who we are.
How does a strong team culture make you feel more connected to your day-to-day work?
A strong culture doesn’t just keep people; it supercharges them by making each day feel purposeful, supported and part of a collective mission. The magic truly happens when our employees have an emotional connection with our work.
Attain's real-time measurement and optimization solutions coupled with high-fidelity audiences and proprietary insights enable marketers to drive valuable outcomes like gaining new customers, retaining existing customers and increasing customer lifetime value.
Describe your sales team culture in one word. Why did you choose that word?
Driven. Our sales team is best described as driven and results-oriented because everything we do is rooted in performance, accountability and forward momentum. We're motivated by clear goals and a shared commitment to exceeding them — not just meeting quotas but constantly pushing the boundaries of what's possible.
Each team member takes ownership of their pipeline and outcomes, showing up every day with a strong work ethic, competitive spirit and hunger to improve. Wins are celebrated, challenges are met head-on and data is used not just to measure success but to sharpen our strategy.
In a driven culture, we work together to find opportunities and support each other as we grow to meet new expectations. Ultimately, we’re all working toward a common goal which is to drive the business forward.
What are your team’s traditions or growth opportunities, and how do these traditions help team members connect, evolve and stay motivated?
Our team has built a set of traditions that bring energy, collaboration and a sense of shared purpose to our culture. Internal pitch sessions give team members a chance to sharpen their storytelling, learn from each other and celebrate individual strengths in a supportive environment. During offsites, we take on team projects that stretch our thinking and spark creativity — helping us break out of our day-to-day routines and reconnect as a group.
We also regularly practice role-playing different sales scenarios, which not only strengthens our techniques but builds trust and camaraderie. (We make sure to make them a little fun, too.) These traditions aren’t just about getting better at the job — they’re about building a team that’s aligned, motivated and always learning together.
How does a strong team culture make you feel more connected to your day-to-day work?
Coming to the office with a driven, results-oriented sales team makes every day feel more meaningful — like you’re part of something bigger than just your individual goals. It creates a sense of shared momentum, where we celebrate wins together and challenges are tackled as a team. You’re motivated to show up, contribute and grow when you know you’re supported, trusted and working alongside people who genuinely care about each other’s success.
It also brings consistency and clarity — you understand what’s expected, what matters and how your work connects to the broader mission at Attain. In that kind of environment, even routine tasks feel more purposeful because you’re not just working on a team — but you feel like you’re helping to shape it.
Toro TMS is on a mission to deliver technology that drives lasting improvements for the trucking industry.
Describe your sales team culture in one word. Why did you choose that word?
At Toro TMS, we’re a startup stepping into a new market with a product that’s still earning its place. That’s why we never take anyone’s time, attention or trust for granted. Every interaction is an opportunity we deeply respect.
Our sales team embodies grit. We show up every day with resilience, persistence and a relentless dive toward long-term success. Challenges don’t deter us, they sharpen us. Grit is what fuels our growth, shapes our culture and keeps us moving forward even when it gets tough.
If you’re looking for a team where perseverance is celebrated, where obstacles are seen as stepping stones and where your work truly makes an impact, you’ll find your place here.
What are your team’s traditions or growth opportunities, and how do these traditions help team members connect, evolve and stay motivated?
We're very lucky that Toro is filled with opportunity. Being at an early-stage company means your personal growth can mirror the company’s trajectory if you’re willing to put in the work. On our team, growth isn’t left to chance — instead we have clearly defined career progression milestones and we’re intentional about developing talent from day one. The SDR role, while foundational, is built as a launchpad, not a destination. We’re proud to help early-stage professionals carve out paths that align with their strengths and ambitions while solving real company needs. This shared sense of purpose and momentum keeps our team connected and motivated about what’s ahead.
How does a strong team culture make you feel more connected to your day-to-day work?
At Toro, we are building a culture that gets a little better every day. We focus on helping customers, supporting each other and compounding trust and results over time. Our three core cultural pillars — Be a Company Builder, Enjoy the Ride and Earn the Right — guide everything we do. They remind us that each call, each meeting and each moment is a chance to build something meaningful together. That sense of shared purpose makes the day-to-day work feel bigger than just hitting quota, but about shaping the future of Toro and the bulk trucking space.
